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https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=5010
It:Retinal
2006-11-07T12:53:59Z
<p>So105: /* The role of retinal in the vision process */fixed molecule b</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''', also known as retinaldehyde or retinene<sub>1</sub> is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="1" bgcolor="lt blue"|<br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Cis-Retinal''' <br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Trans-Retinal''' <br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''<br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''<br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)<br />
=C(C)CCC1<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)<br />
=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
|[[Image:AllTransRetinal.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY BOKSEZ<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 14.761 8.292 15.210 90.00 102.40 90.00 P 21/n 4<br />
ATOM 1 O1 UNK 0 1 8.800 1.137 3.735 1.00 0.00<br />
ATOM 2 O2 UNK 0 1 -3.642 0.109 -1.855 1.00 0.00<br />
ATOM 3 C1 UNK 0 1 7.236 4.986 3.316 1.00 0.00<br />
ATOM 4 C2 UNK 0 1 7.808 4.433 4.641 1.00 0.00<br />
ATOM 5 C3 UNK 0 1 8.881 3.407 4.434 1.00 0.00<br />
ATOM 6 C4 UNK 0 1 8.402 2.292 3.586 1.00 0.00<br />
ATOM 7 C5 UNK 0 1 7.434 2.593 2.496 1.00 0.00<br />
ATOM 8 C6 UNK 0 1 6.851 3.816 2.410 1.00 0.00<br />
ATOM 9 C7 UNK 0 1 5.849 4.111 1.365 1.00 0.00<br />
ATOM 10 C8 UNK 0 1 4.735 3.412 1.188 1.00 0.00<br />
ATOM 11 C9 UNK 0 1 3.695 3.741 0.202 1.00 0.00<br />
ATOM 12 C10 UNK 0 1 2.601 2.943 0.227 1.00 0.00<br />
ATOM 13 C11 UNK 0 1 1.409 3.020 -0.654 1.00 0.00<br />
ATOM 14 C12 UNK 0 1 0.394 2.212 -0.535 1.00 0.00<br />
ATOM 15 C13 UNK 0 1 -0.769 2.174 -1.450 1.00 0.00<br />
ATOM 16 C14 UNK 0 1 -1.684 1.256 -1.236 1.00 0.00<br />
ATOM 17 C15 UNK 0 1 -2.881 0.999 -2.043 1.00 0.00<br />
ATOM 18 C16 UNK 0 1 7.167 1.427 1.567 1.00 0.00<br />
ATOM 19 C17 UNK 0 1 5.974 5.755 3.760 1.00 0.00<br />
ATOM 20 C18 UNK 0 1 8.204 5.906 2.607 1.00 0.00<br />
ATOM 21 C19 UNK 0 1 3.919 4.853 -0.787 1.00 0.00<br />
ATOM 22 C20 UNK 0 1 -0.796 3.178 -2.557 1.00 0.00<br />
ATOM 23 H1 UNK 0 1 6.939 4.113 5.229 1.00 0.00<br />
ATOM 24 H2 UNK 0 1 8.383 5.232 5.110 1.00 0.00<br />
ATOM 25 H3 UNK 0 1 9.085 3.458 5.274 1.00 0.00<br />
ATOM 26 H4 UNK 0 1 9.452 3.930 3.803 1.00 0.00<br />
ATOM 27 H5 UNK 0 1 6.133 4.784 0.772 1.00 0.00<br />
ATOM 28 H6 UNK 0 1 4.476 2.728 1.797 1.00 0.00<br />
ATOM 29 H7 UNK 0 1 2.453 2.222 0.995 1.00 0.00<br />
ATOM 30 H8 UNK 0 1 1.583 3.856 -1.292 1.00 0.00<br />
ATOM 31 H9 UNK 0 1 0.154 1.750 0.238 1.00 0.00<br />
ATOM 32 H10 UNK 0 1 -1.746 0.871 -0.520 1.00 0.00<br />
ATOM 33 H11 UNK 0 1 -2.722 1.857 -2.659 1.00 0.00<br />
ATOM 34 H12 UNK 0 1 5.584 6.194 3.134 1.00 0.00<br />
ATOM 35 H13 UNK 0 1 5.249 5.174 4.323 1.00 0.00<br />
ATOM 36 H14 UNK 0 1 6.345 6.509 4.442 1.00 0.00<br />
ATOM 37 H15 UNK 0 1 7.632 6.136 2.080 1.00 0.00<br />
ATOM 38 H16 UNK 0 1 9.036 5.224 2.674 1.00 0.00<br />
ATOM 39 H17 UNK 0 1 8.192 0.796 1.411 1.00 0.00<br />
ATOM 40 H18 UNK 0 1 6.845 1.683 0.891 1.00 0.00<br />
ATOM 41 H19 UNK 0 1 6.601 0.730 1.664 1.00 0.00<br />
ATOM 42 H20 UNK 0 1 3.287 5.000 -1.055 1.00 0.00<br />
ATOM 43 H21 UNK 0 1 3.641 5.431 -0.312 1.00 0.00<br />
ATOM 44 H22 UNK 0 1 4.744 4.677 -1.233 1.00 0.00<br />
ATOM 45 H23 UNK 0 1 -1.169 2.952 -3.075 1.00 0.00<br />
ATOM 46 H24 UNK 0 1 -1.270 3.988 -2.080 1.00 0.00<br />
ATOM 47 H25 UNK 0 1 -0.054 3.018 -3.313 1.00 0.00<br />
CONECT 1 6<br />
CONECT 2 17<br />
CONECT 3 4 8 19 20<br />
CONECT 4 3 5 23 24<br />
CONECT 5 4 6 25 26<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 18<br />
CONECT 8 3 7 9<br />
CONECT 9 8 10 27<br />
CONECT 10 9 11 28<br />
CONECT 11 10 12 21<br />
CONECT 12 11 13 29<br />
CONECT 13 12 14 30<br />
CONECT 14 13 15 31<br />
CONECT 15 14 16 22<br />
CONECT 16 15 17 32<br />
CONECT 17 2 16 33<br />
CONECT 18 7 39 40 41<br />
CONECT 19 3 34 35 36<br />
CONECT 20 3 37 38<br />
CONECT 21 11 42 43 44<br />
CONECT 22 15 45 46 47<br />
CONECT 23 4<br />
CONECT 24 4<br />
CONECT 25 5<br />
CONECT 26 5<br />
CONECT 27 9<br />
CONECT 28 10<br />
CONECT 29 12<br />
CONECT 30 13<br />
CONECT 31 14<br />
CONECT 32 16<br />
CONECT 33 17<br />
CONECT 34 19<br />
CONECT 35 19<br />
CONECT 36 19<br />
CONECT 37 20<br />
CONECT 38 20<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 18<br />
CONECT 42 21<br />
CONECT 43 21<br />
CONECT 44 21<br />
CONECT 45 22<br />
CONECT 46 22<br />
CONECT 47 22<br />
MASTER 0 0 0 0 0 0 0 0 47 0 47 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="2" bgcolor=""|[http://www.ch.ic.ac.uk/wiki/index.php/Image:Trans-retinal.cdx ChemDraw 3D structure]<br />
|}<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''Structure A'''<br />
| align="center" bgcolor="lt blue"|'''Structure B'''<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY CRETAL01<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 13.180 7.499 17.803 90.00 95.66 90.00 P 21/n 4<br />
ATOM 1 C1 UNK 0 1 3.279 5.402 15.975 1.00 0.00<br />
ATOM 2 C2 UNK 0 1 4.046 6.337 15.055 1.00 0.00<br />
ATOM 3 C3 UNK 0 1 3.501 7.731 15.036 1.00 0.00<br />
ATOM 4 C4 UNK 0 1 2.048 7.716 14.547 1.00 0.00<br />
ATOM 5 C5 UNK 0 1 1.242 6.570 15.071 1.00 0.00<br />
ATOM 6 C6 UNK 0 1 1.742 5.525 15.720 1.00 0.00<br />
ATOM 7 C7 UNK 0 1 0.960 4.412 16.249 1.00 0.00<br />
ATOM 8 C8 UNK 0 1 -0.096 3.785 15.688 1.00 0.00<br />
ATOM 9 C9 UNK 0 1 -0.891 2.748 16.260 1.00 0.00<br />
ATOM 10 C10 UNK 0 1 -2.039 2.359 15.656 1.00 0.00<br />
ATOM 11 C11 UNK 0 1 -2.995 1.432 16.171 1.00 0.00<br />
ATOM 12 C12 UNK 0 1 -4.118 0.952 15.603 1.00 0.00<br />
ATOM 13 C13 UNK 0 1 -4.579 1.155 14.210 1.00 0.00<br />
ATOM 14 C14 UNK 0 1 -3.772 1.162 13.168 1.00 0.00<br />
ATOM 15 C15 UNK 0 1 -4.144 1.290 11.748 1.00 0.00<br />
ATOM 16 O1 UNK 0 1 -3.417 1.200 10.832 1.00 0.00<br />
ATOM 17 C16 UNK 0 1 -0.251 6.757 14.825 1.00 0.00<br />
ATOM 18 C17 UNK 0 1 3.537 5.722 17.465 1.00 0.00<br />
ATOM 19 C18 UNK 0 1 3.755 3.989 15.704 1.00 0.00<br />
ATOM 20 C19 UNK 0 1 -0.446 2.130 17.555 1.00 0.00<br />
ATOM 21 C20 UNK 0 1 -6.097 1.275 14.125 1.00 0.00<br />
ATOM 22 H1 UNK 0 1 4.961 6.299 15.236 1.00 0.00<br />
ATOM 23 H2 UNK 0 1 4.033 6.074 13.960 1.00 0.00<br />
ATOM 24 H3 UNK 0 1 3.361 8.099 16.086 1.00 0.00<br />
ATOM 25 H4 UNK 0 1 4.112 8.346 14.368 1.00 0.00<br />
ATOM 26 H5 UNK 0 1 1.613 8.609 14.846 1.00 0.00<br />
ATOM 27 H6 UNK 0 1 2.096 8.271 13.429 1.00 0.00<br />
ATOM 28 H7 UNK 0 1 1.167 4.027 17.220 1.00 0.00<br />
ATOM 29 H8 UNK 0 1 -0.283 4.132 14.828 1.00 0.00<br />
ATOM 30 H9 UNK 0 1 -2.166 2.700 14.811 1.00 0.00<br />
ATOM 31 H10 UNK 0 1 -2.959 1.140 17.220 1.00 0.00<br />
ATOM 32 H11 UNK 0 1 -4.766 0.337 16.175 1.00 0.00<br />
ATOM 33 H12 UNK 0 1 -2.863 1.012 13.199 1.00 0.00<br />
ATOM 34 H13 UNK 0 1 -5.051 1.500 11.604 1.00 0.00<br />
ATOM 35 H14 UNK 0 1 -0.500 7.641 14.882 1.00 0.00<br />
ATOM 36 H15 UNK 0 1 -0.354 6.404 13.677 1.00 0.00<br />
ATOM 37 H16 UNK 0 1 -0.828 6.374 15.537 1.00 0.00<br />
ATOM 38 H17 UNK 0 1 4.443 5.482 17.539 1.00 0.00<br />
ATOM 39 H18 UNK 0 1 3.171 6.749 17.876 1.00 0.00<br />
ATOM 40 H19 UNK 0 1 2.971 5.092 18.159 1.00 0.00<br />
ATOM 41 H20 UNK 0 1 3.359 3.330 16.246 1.00 0.00<br />
ATOM 42 H21 UNK 0 1 3.564 3.712 14.704 1.00 0.00<br />
ATOM 43 H22 UNK 0 1 4.832 3.967 15.608 1.00 0.00<br />
ATOM 44 H23 UNK 0 1 0.526 2.025 17.433 1.00 0.00<br />
ATOM 45 H24 UNK 0 1 -0.489 2.700 18.230 1.00 0.00<br />
ATOM 46 H25 UNK 0 1 -1.006 1.387 18.000 1.00 0.00<br />
ATOM 47 H26 UNK 0 1 -6.646 0.300 14.793 1.00 0.00<br />
ATOM 48 H27 UNK 0 1 -6.440 2.100 14.580 1.00 0.00<br />
ATOM 49 H28 UNK 0 1 -6.271 1.320 13.269 1.00 0.00<br />
CONECT 1 2 6 18 19<br />
CONECT 2 1 3 22 23<br />
CONECT 3 2 4 24 25<br />
CONECT 4 3 5 26 27<br />
CONECT 5 4 6 17<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 28<br />
CONECT 8 7 9 29<br />
CONECT 9 8 10 20<br />
CONECT 10 9 11 30<br />
CONECT 11 10 12 31<br />
CONECT 12 11 13 32<br />
CONECT 13 12 14 21<br />
CONECT 14 13 15 33<br />
CONECT 15 14 16 34<br />
CONECT 16 15<br />
CONECT 17 5 35 36 37<br />
CONECT 18 1 38 39 40<br />
CONECT 19 1 41 42 43<br />
CONECT 20 9 44 45 46<br />
CONECT 21 13 47 48 49<br />
CONECT 22 2<br />
CONECT 23 2<br />
CONECT 24 3<br />
CONECT 25 3<br />
CONECT 26 4<br />
CONECT 27 4<br />
CONECT 28 7<br />
CONECT 29 8<br />
CONECT 30 10<br />
CONECT 31 11<br />
CONECT 32 12<br />
CONECT 33 14<br />
CONECT 34 15<br />
CONECT 35 17<br />
CONECT 36 17<br />
CONECT 37 17<br />
CONECT 38 18<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 19<br />
CONECT 42 19<br />
CONECT 43 19<br />
CONECT 44 20<br />
CONECT 45 20<br />
CONECT 46 20<br />
CONECT 47 21<br />
CONECT 48 21<br />
CONECT 49 21<br />
MASTER 0 0 0 0 0 0 0 0 49 0 49 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY BOKSEZ<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 14.761 8.292 15.210 90.00 102.40 90.00 P 21/n 4<br />
ATOM 1 O1 UNK 0 1 8.800 1.137 3.735 1.00 0.00<br />
ATOM 2 O2 UNK 0 1 -3.642 0.109 -1.855 1.00 0.00<br />
ATOM 3 C1 UNK 0 1 7.236 4.986 3.316 1.00 0.00<br />
ATOM 4 C2 UNK 0 1 7.808 4.433 4.641 1.00 0.00<br />
ATOM 5 C3 UNK 0 1 8.881 3.407 4.434 1.00 0.00<br />
ATOM 6 C4 UNK 0 1 8.402 2.292 3.586 1.00 0.00<br />
ATOM 7 C5 UNK 0 1 7.434 2.593 2.496 1.00 0.00<br />
ATOM 8 C6 UNK 0 1 6.851 3.816 2.410 1.00 0.00<br />
ATOM 9 C7 UNK 0 1 5.849 4.111 1.365 1.00 0.00<br />
ATOM 10 C8 UNK 0 1 4.735 3.412 1.188 1.00 0.00<br />
ATOM 11 C9 UNK 0 1 3.695 3.741 0.202 1.00 0.00<br />
ATOM 12 C10 UNK 0 1 2.601 2.943 0.227 1.00 0.00<br />
ATOM 13 C11 UNK 0 1 1.409 3.020 -0.654 1.00 0.00<br />
ATOM 14 C12 UNK 0 1 0.394 2.212 -0.535 1.00 0.00<br />
ATOM 15 C13 UNK 0 1 -0.769 2.174 -1.450 1.00 0.00<br />
ATOM 16 C14 UNK 0 1 -1.684 1.256 -1.236 1.00 0.00<br />
ATOM 17 C15 UNK 0 1 -2.881 0.999 -2.043 1.00 0.00<br />
ATOM 18 C16 UNK 0 1 7.167 1.427 1.567 1.00 0.00<br />
ATOM 19 C17 UNK 0 1 5.974 5.755 3.760 1.00 0.00<br />
ATOM 20 C18 UNK 0 1 8.204 5.906 2.607 1.00 0.00<br />
ATOM 21 C19 UNK 0 1 3.919 4.853 -0.787 1.00 0.00<br />
ATOM 22 C20 UNK 0 1 -0.796 3.178 -2.557 1.00 0.00<br />
ATOM 23 H1 UNK 0 1 6.939 4.113 5.229 1.00 0.00<br />
ATOM 24 H2 UNK 0 1 8.383 5.232 5.110 1.00 0.00<br />
ATOM 25 H3 UNK 0 1 9.085 3.458 5.274 1.00 0.00<br />
ATOM 26 H4 UNK 0 1 9.452 3.930 3.803 1.00 0.00<br />
ATOM 27 H5 UNK 0 1 6.133 4.784 0.772 1.00 0.00<br />
ATOM 28 H6 UNK 0 1 4.476 2.728 1.797 1.00 0.00<br />
ATOM 29 H7 UNK 0 1 2.453 2.222 0.995 1.00 0.00<br />
ATOM 30 H8 UNK 0 1 1.583 3.856 -1.292 1.00 0.00<br />
ATOM 31 H9 UNK 0 1 0.154 1.750 0.238 1.00 0.00<br />
ATOM 32 H10 UNK 0 1 -1.746 0.871 -0.520 1.00 0.00<br />
ATOM 33 H11 UNK 0 1 -2.722 1.857 -2.659 1.00 0.00<br />
ATOM 34 H12 UNK 0 1 5.584 6.194 3.134 1.00 0.00<br />
ATOM 35 H13 UNK 0 1 5.249 5.174 4.323 1.00 0.00<br />
ATOM 36 H14 UNK 0 1 6.345 6.509 4.442 1.00 0.00<br />
ATOM 37 H15 UNK 0 1 7.632 6.136 2.080 1.00 0.00<br />
ATOM 38 H16 UNK 0 1 9.036 5.224 2.674 1.00 0.00<br />
ATOM 39 H17 UNK 0 1 8.192 0.796 1.411 1.00 0.00<br />
ATOM 40 H18 UNK 0 1 6.845 1.683 0.891 1.00 0.00<br />
ATOM 41 H19 UNK 0 1 6.601 0.730 1.664 1.00 0.00<br />
ATOM 42 H20 UNK 0 1 3.287 5.000 -1.055 1.00 0.00<br />
ATOM 43 H21 UNK 0 1 3.641 5.431 -0.312 1.00 0.00<br />
ATOM 44 H22 UNK 0 1 4.744 4.677 -1.233 1.00 0.00<br />
ATOM 45 H23 UNK 0 1 -1.169 2.952 -3.075 1.00 0.00<br />
ATOM 46 H24 UNK 0 1 -1.270 3.988 -2.080 1.00 0.00<br />
ATOM 47 H25 UNK 0 1 -0.054 3.018 -3.313 1.00 0.00<br />
CONECT 1 6<br />
CONECT 2 17<br />
CONECT 3 4 8 19 20<br />
CONECT 4 3 5 23 24<br />
CONECT 5 4 6 25 26<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 18<br />
CONECT 8 3 7 9<br />
CONECT 9 8 10 27<br />
CONECT 10 9 11 28<br />
CONECT 11 10 12 21<br />
CONECT 12 11 13 29<br />
CONECT 13 12 14 30<br />
CONECT 14 13 15 31<br />
CONECT 15 14 16 22<br />
CONECT 16 15 17 32<br />
CONECT 17 2 16 33<br />
CONECT 18 7 39 40 41<br />
CONECT 19 3 34 35 36<br />
CONECT 20 3 37 38<br />
CONECT 21 11 42 43 44<br />
CONECT 22 15 45 46 47<br />
CONECT 23 4<br />
CONECT 24 4<br />
CONECT 25 5<br />
CONECT 26 5<br />
CONECT 27 9<br />
CONECT 28 10<br />
CONECT 29 12<br />
CONECT 30 13<br />
CONECT 31 14<br />
CONECT 32 16<br />
CONECT 33 17<br />
CONECT 34 19<br />
CONECT 35 19<br />
CONECT 36 19<br />
CONECT 37 20<br />
CONECT 38 20<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 18<br />
CONECT 42 21<br />
CONECT 43 21<br />
CONECT 44 21<br />
CONECT 45 22<br />
CONECT 46 22<br />
CONECT 47 22<br />
MASTER 0 0 0 0 0 0 0 0 47 0 47 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
==Effects of Bunazosin on ocular circulation and retinal neuronal damage==<br />
<br />
By applying bunazosin hydrochloride into a healthy humans, it increases the blood velocity in the optic nerve head(ONH),retina and choroid, without changing either heart rate and blood pressure dramaticallt. This drug was also applied to rabbits and rats, giving positive results. These shows that bunazosin hydrochloride have improvement effect both in the ocular circulation and a direct neuroprotective effct. Therefore, it may be useful to use bunazosin hydrochloride as a therapeutic drug against retinal diseases which is associated with the ocular circulation.<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.<br />
*3.Hara, Hideaki / Ichikawa, Masaki / Oku, Hidehiro / Shimazawa, Masamitsu / Araie, Makoto, Cardiovascular drug reviews, Apr 2005</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Serotonin&diff=4997
It:Serotonin
2006-11-07T11:56:41Z
<p>So105: /* Serotonin: Interesting Thoughts */spelling and grammar correction</p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}} colspan="3" |2D Structure <br />
|-<br />
| align="center" colspan="3" bgcolour="#ffffff" | [[image:Serotonin.gif]] <br />
|-<br />
! {{chembox header}} colspan="3" |3D structure <jmol><br />
<jmolApplet><br />
<size>310</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 24-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 24-Oct-06 0 NONE 4<br />
ATOM 1 N 0 4.143 1.513 0.282 0.00 0.00 N+0<br />
ATOM 2 C 0 2.960 0.702 0.600 0.00 0.00 C+0<br />
ATOM 3 C 0 2.369 0.133 -0.691 0.00 0.00 C+0<br />
ATOM 4 C 0 1.156 -0.699 -0.365 0.00 0.00 C+0<br />
ATOM 5 C 0 1.124 -2.029 -0.185 0.00 0.00 C+0<br />
ATOM 6 N 0 -0.152 -2.432 0.097 0.00 0.00 N+0<br />
ATOM 7 C 0 -0.996 -1.341 0.105 0.00 0.00 C+0<br />
ATOM 8 C 0 -0.212 -0.209 -0.178 0.00 0.00 C+0<br />
ATOM 9 C 0 -0.805 1.055 -0.237 0.00 0.00 C+0<br />
ATOM 10 C 0 -2.162 1.182 -0.015 0.00 0.00 C+0<br />
ATOM 11 O 0 -2.745 2.409 -0.071 0.00 0.00 O+0<br />
ATOM 12 C 0 -2.936 0.058 0.265 0.00 0.00 C+0<br />
ATOM 13 C 0 -2.361 -1.191 0.330 0.00 0.00 C+0<br />
ATOM 14 H 0 3.815 2.311 -0.241 0.00 0.00 H+0<br />
ATOM 15 H 0 4.497 1.865 1.159 0.00 0.00 H+0<br />
ATOM 16 H 0 3.247 -0.117 1.260 0.00 0.00 H+0<br />
ATOM 17 H 0 2.215 1.324 1.097 0.00 0.00 H+0<br />
ATOM 18 H 0 2.082 0.952 -1.351 0.00 0.00 H+0<br />
ATOM 19 H 0 3.113 -0.490 -1.188 0.00 0.00 H+0<br />
ATOM 20 H 0 1.980 -2.684 -0.252 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.424 -3.347 0.266 0.00 0.00 H+0<br />
ATOM 22 H 0 -0.206 1.926 -0.454 0.00 0.00 H+0<br />
ATOM 23 H 0 -3.024 2.545 -0.987 0.00 0.00 H+0<br />
ATOM 24 H 0 -3.996 0.169 0.437 0.00 0.00 H+0<br />
ATOM 25 H 0 -2.971 -2.055 0.547 0.00 0.00 H+0<br />
CONECT 1 2 14 15 0 NONE 30<br />
CONECT 2 1 3 16 17 NONE 31<br />
CONECT 3 2 4 18 19 NONE 32<br />
CONECT 4 3 8 5 0 NONE 33<br />
CONECT 5 4 6 20 0 NONE 34<br />
CONECT 6 5 7 21 0 NONE 35<br />
CONECT 7 6 13 8 0 NONE 36<br />
CONECT 8 7 4 9 0 NONE 37<br />
CONECT 9 8 10 22 0 NONE 38<br />
CONECT 10 9 11 12 0 NONE 39<br />
CONECT 11 10 23 0 0 NONE 40<br />
CONECT 12 10 13 24 0 NONE 41<br />
CONECT 13 12 7 25 0 NONE 42<br />
END NONE 43<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
!{{chembox header}} colspan="3" | Properties<br />
|-<br />
|colspan="1"|IUPAC Systematic Name<br />
|colspan="2"|5-Hydroxytryptamine/<br />
3-(2-aminoethyl)-1H-indol-5-ol<br />
|-<br />
|colspan="1"|Chemical Name<br />
|colspan="2"|3-(2-Amino-aethyl)-indol-5-ol<br />
|-<br />
|colspan="1"|Molecular formula<br />
|colspan="2"|C<sub>10</sub>H<sub>12</sub>N<sub>2</sub>O<br />
|-<br />
|colspan="1"|Molecular Mass<br />
|colspan="2"|176.2182 gmol<sup>-1</sup><br />
|-<br />
|colspan="1"|Type of Substance<br />
|colspan="2"|heterocyclic<br />
|-<br />
|colspan="1"|CAS Registry Number<br />
|colspan="2"|50-67-9, 61-47-2<br />
|-<br />
|colspan="1"|SMILES String<br />
|colspan="2"|NCCC1=CNC2=C1C=C(O)C=C2<br />
|-<br />
|}<br />
<br />
==What is Serotonin==<br />
<br />
*Serotonin is a hormone manufactured by the brain that is associated with opiate-specific receptors - so helps maintain a happy feeling.<br />
*It is a neurotransmitter meaning that is a chemical messenger in the brain which allows the brain to communicate with nerve cells.<br />
*The most effective way of increasing serotonin levels is vigorous exercise if the person only has very mild depression. This exercise increases the levels for many days after the exercise takes place. <br />
*Your diet will also effect the levels of serotonin. Low levels of omega 3 and vitamin C in the diet will cause a reduction in the amount of serotonin in the body.<br />
<br />
==What Does Serotonin Do==<br />
<br />
Serotonin affects many basic psychological functions such as <br />
anxiety mechanisms and the regulation of mood, thoughts, aggression, <br />
appetite, sex drive and the sleep/wake cycle. Multiple observations suggest that serotonin, one of <br />
the most abundant neurotransmitters, plays an important role in the regulation of mood and a key role <br />
in the treatment of depression. <br />
<br />
Due to this, lack of serotonin is often associated with depression. Restoring the normal or enhanced level of this neurotransmitter acts as mood enhancer. Prozac is a mood enhancing drug, which acts in the central nervous system by inhibiting the reuptake mechanism of serotonin into the synapse. Since serotonin is not degraded in the synaptic cleft, Prozac promotes a prolonged presence of serotonin keeping the post-synaptic membrane active.<br />
<br />
In the central nervous system, serotonin is involved in fear and flight responses, an activity which is opposed by the aggression stimulating hormone adrenaline (epinephrine) and neurotransmitter dopamine.<br />
<br />
Light modulates the production of certain hormones and brain chemicals, such as serotonin. The amount of serotonin in your brain reflects the amount of light in your environment. More light = more serotonin = more energy, a better mood, and fewer carbohydrate cravings!<br />
<br />
==Serotonin in our bodies==<br />
<br />
Serotonin originates in neurons deep in the midline of the brainstem. Because these neurons profile diffusely throughout the brain, serotonin can affect various brain functions, such as depression. It also interacts with many other neurotransmitters, either directly through neurons that use both serotonin and another neurotransmitter, or by serotonin neurons influencing neurons that primarily use these other transmitters. <br />
<br />
Serotonin can be found in three main areas of the body: the intestinal wall, blood vessels, and the central nervous system.<br />
<br />
==Sources of Serotonin==<br />
<br />
*It is manufactured in the human brain using the essential amino acid tryptophan which is found in pineapples, plums, turkey and milk.<br />
*Bananas contain tryptophan, which the body converts into serotonin, known to make you relax, improve your mood and generally make you feel happier.<br />
*Tryptophan is also found in chocolate, again causing the release of serotonin; which is often why it is eaten as a comfort food.<br />
<br />
==Synthesis of Serotonin==<br />
<br />
Serotonin is synthesized from the amino acid precursor tryptophan, packaged into vesicles, and <br />
released into the synapse following an action potential. Once in the synapse, serotonin can interact <br />
with both the pre- and postsynaptic receptors.<br />
<br />
[[Image:synthesisSerotonin.gif|thumb|synthesis of serotonin]]<br />
[http://www.chm.bris.ac.uk/motm/serotonin/synthesis.htm 1]<br />
<br />
'''Detail of Synthesis:'''<br />
[[image:detail_of_serotonin_synthesis.GIF]] [http://www.neurosci.pharm.utoledo.edu/MBC3320/serotonin.htm]<br />
<br />
==Images of Serotonin==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''Electron Density of Serotonin''' <br />
| bgcolor="lt blue"|'''Electrostatic Potential of Serotonin'''<br />
|-<br />
|[[image:Electron_density_of_serotonin.GIF]]<br />
|[[image:electrostatic_potential_of_serotonin.GIF]]<br />
<br />
|-<br />
|}[http://www.cmste.uncc.edu/new/Document%20Hold/Sawsun-%20Serotonin%20FINAL%20PAPER.doc]<br />
<br />
==Serotonin: Interesting Thoughts==<br />
<br />
*Studies show that there is a chemical hierarchy in humans associated with social "rank" that is linked with serotonin levels. Those in high office, higher positions on sports teams and those of higher rank in academic clubs have been found to have higher levels of serotonin than their lower ranking peers. [http://www.globalhypnosis.com/hypnosis_stories.html]<br />
<br />
*Serotonergic activity gradually decreases as one becomes drowsy and enters slow-wave sleep. An overall slowing of serotonergic activity is observed during slow-wave sleep known as non-REM sleep. During REM sleep (Rapid Eye Movement-the original dream sleep), serotonergic activity falls completely silent. Serotonergic activity returns to its basic level several seconds prior to the end of REM sleep. [http://www.antidepressantsfacts.com/pinealstory.htm]<br />
<br />
*The stimulant in the drug Ecstasy forces the brain to release serotonin, in abnormally large amounts. The neurons (brain cells) that store serotonin are deformed or destroyed. Scientists have found that these injured neurons can regrow, but they may grow back abnormally or in the wrong locations. When Ecstasy wears off, the overflow of serotonin reverses to a lack of serotonin. Without enough serotonin it is difficult to sleep, learn, remember, or feel happy. [http://www.intheknowzone.com/ecstasy/chemistry.htm]<br />
<br />
*When UV light interacts with your skin, it triggers the formation of vitamin D. Vitamin D stimulates the production of feel-good brain chemicals such as serotonin and dopamine. <br />
<br />
*The light that enters your eyes has an immediate effect on your mood, so bright light, especially blue light (around the wavelength 460 nm) shuts down the production of melatonin, the night-time sleep hormone, and stimulates the production of serotonin, its energising, daytime counterpart.<br />
<br />
==References==<br />
*[http://www.healthscout.com/ency/1/409/main.html/ Healthscout]- What does Serotonin do?<br />
*[http://www.chm.bris.ac.uk/motm/serotonin/synthesis.htm/ University of Bristol: Chemistry]- Synthesis of Serotonin<br />
*[http://www.neurosci.pharm.utoledo.edu/MBC3320/serotonin.htm/ MBC Serotonin]- Detail of Synthesis<br />
*[http://www.cmste.uncc.edu/ CMSTE]- Images of Serotonin<br />
*[http://www.angelfire.com/hi/TheSeer/seratonin.html/ Serotonin]- What does Serotonin do?<br />
*[http://www.thebodyblues.com/light.html/The Body Blues]- What does Serotonin do?<br />
*[Belstein (2006/03]- Properties</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=4993
It:Retinal
2006-11-07T11:50:20Z
<p>So105: /* The role of retinal in the vision process */ changed layout of 3D images</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''', also known as retinaldehyde or retinene<sub>1</sub> is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="1" bgcolor="lt blue"|<br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Cis-Retinal''' <br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Trans-Retinal''' <br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''<br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''<br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)<br />
=C(C)CCC1<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)<br />
=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
|[[Image:AllTransRetinal.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY BOKSEZ<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 14.761 8.292 15.210 90.00 102.40 90.00 P 21/n 4<br />
ATOM 1 O1 UNK 0 1 8.800 1.137 3.735 1.00 0.00<br />
ATOM 2 O2 UNK 0 1 -3.642 0.109 -1.855 1.00 0.00<br />
ATOM 3 C1 UNK 0 1 7.236 4.986 3.316 1.00 0.00<br />
ATOM 4 C2 UNK 0 1 7.808 4.433 4.641 1.00 0.00<br />
ATOM 5 C3 UNK 0 1 8.881 3.407 4.434 1.00 0.00<br />
ATOM 6 C4 UNK 0 1 8.402 2.292 3.586 1.00 0.00<br />
ATOM 7 C5 UNK 0 1 7.434 2.593 2.496 1.00 0.00<br />
ATOM 8 C6 UNK 0 1 6.851 3.816 2.410 1.00 0.00<br />
ATOM 9 C7 UNK 0 1 5.849 4.111 1.365 1.00 0.00<br />
ATOM 10 C8 UNK 0 1 4.735 3.412 1.188 1.00 0.00<br />
ATOM 11 C9 UNK 0 1 3.695 3.741 0.202 1.00 0.00<br />
ATOM 12 C10 UNK 0 1 2.601 2.943 0.227 1.00 0.00<br />
ATOM 13 C11 UNK 0 1 1.409 3.020 -0.654 1.00 0.00<br />
ATOM 14 C12 UNK 0 1 0.394 2.212 -0.535 1.00 0.00<br />
ATOM 15 C13 UNK 0 1 -0.769 2.174 -1.450 1.00 0.00<br />
ATOM 16 C14 UNK 0 1 -1.684 1.256 -1.236 1.00 0.00<br />
ATOM 17 C15 UNK 0 1 -2.881 0.999 -2.043 1.00 0.00<br />
ATOM 18 C16 UNK 0 1 7.167 1.427 1.567 1.00 0.00<br />
ATOM 19 C17 UNK 0 1 5.974 5.755 3.760 1.00 0.00<br />
ATOM 20 C18 UNK 0 1 8.204 5.906 2.607 1.00 0.00<br />
ATOM 21 C19 UNK 0 1 3.919 4.853 -0.787 1.00 0.00<br />
ATOM 22 C20 UNK 0 1 -0.796 3.178 -2.557 1.00 0.00<br />
ATOM 23 H1 UNK 0 1 6.939 4.113 5.229 1.00 0.00<br />
ATOM 24 H2 UNK 0 1 8.383 5.232 5.110 1.00 0.00<br />
ATOM 25 H3 UNK 0 1 9.085 3.458 5.274 1.00 0.00<br />
ATOM 26 H4 UNK 0 1 9.452 3.930 3.803 1.00 0.00<br />
ATOM 27 H5 UNK 0 1 6.133 4.784 0.772 1.00 0.00<br />
ATOM 28 H6 UNK 0 1 4.476 2.728 1.797 1.00 0.00<br />
ATOM 29 H7 UNK 0 1 2.453 2.222 0.995 1.00 0.00<br />
ATOM 30 H8 UNK 0 1 1.583 3.856 -1.292 1.00 0.00<br />
ATOM 31 H9 UNK 0 1 0.154 1.750 0.238 1.00 0.00<br />
ATOM 32 H10 UNK 0 1 -1.746 0.871 -0.520 1.00 0.00<br />
ATOM 33 H11 UNK 0 1 -2.722 1.857 -2.659 1.00 0.00<br />
ATOM 34 H12 UNK 0 1 5.584 6.194 3.134 1.00 0.00<br />
ATOM 35 H13 UNK 0 1 5.249 5.174 4.323 1.00 0.00<br />
ATOM 36 H14 UNK 0 1 6.345 6.509 4.442 1.00 0.00<br />
ATOM 37 H15 UNK 0 1 7.632 6.136 2.080 1.00 0.00<br />
ATOM 38 H16 UNK 0 1 9.036 5.224 2.674 1.00 0.00<br />
ATOM 39 H17 UNK 0 1 8.192 0.796 1.411 1.00 0.00<br />
ATOM 40 H18 UNK 0 1 6.845 1.683 0.891 1.00 0.00<br />
ATOM 41 H19 UNK 0 1 6.601 0.730 1.664 1.00 0.00<br />
ATOM 42 H20 UNK 0 1 3.287 5.000 -1.055 1.00 0.00<br />
ATOM 43 H21 UNK 0 1 3.641 5.431 -0.312 1.00 0.00<br />
ATOM 44 H22 UNK 0 1 4.744 4.677 -1.233 1.00 0.00<br />
ATOM 45 H23 UNK 0 1 -1.169 2.952 -3.075 1.00 0.00<br />
ATOM 46 H24 UNK 0 1 -1.270 3.988 -2.080 1.00 0.00<br />
ATOM 47 H25 UNK 0 1 -0.054 3.018 -3.313 1.00 0.00<br />
CONECT 1 6<br />
CONECT 2 17<br />
CONECT 3 4 8 19 20<br />
CONECT 4 3 5 23 24<br />
CONECT 5 4 6 25 26<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 18<br />
CONECT 8 3 7 9<br />
CONECT 9 8 10 27<br />
CONECT 10 9 11 28<br />
CONECT 11 10 12 21<br />
CONECT 12 11 13 29<br />
CONECT 13 12 14 30<br />
CONECT 14 13 15 31<br />
CONECT 15 14 16 22<br />
CONECT 16 15 17 32<br />
CONECT 17 2 16 33<br />
CONECT 18 7 39 40 41<br />
CONECT 19 3 34 35 36<br />
CONECT 20 3 37 38<br />
CONECT 21 11 42 43 44<br />
CONECT 22 15 45 46 47<br />
CONECT 23 4<br />
CONECT 24 4<br />
CONECT 25 5<br />
CONECT 26 5<br />
CONECT 27 9<br />
CONECT 28 10<br />
CONECT 29 12<br />
CONECT 30 13<br />
CONECT 31 14<br />
CONECT 32 16<br />
CONECT 33 17<br />
CONECT 34 19<br />
CONECT 35 19<br />
CONECT 36 19<br />
CONECT 37 20<br />
CONECT 38 20<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 18<br />
CONECT 42 21<br />
CONECT 43 21<br />
CONECT 44 21<br />
CONECT 45 22<br />
CONECT 46 22<br />
CONECT 47 22<br />
MASTER 0 0 0 0 0 0 0 0 47 0 47 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="2" bgcolor=""|[http://www.ch.ic.ac.uk/wiki/index.php/Image:Trans-retinal.cdx ChemDraw 3D structure]<br />
|}<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''Structure A'''<br />
| align="center" bgcolor="lt blue"|'''Structure B'''<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY CRETAL01<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 13.180 7.499 17.803 90.00 95.66 90.00 P 21/n 4<br />
ATOM 1 C1 UNK 0 1 3.279 5.402 15.975 1.00 0.00<br />
ATOM 2 C2 UNK 0 1 4.046 6.337 15.055 1.00 0.00<br />
ATOM 3 C3 UNK 0 1 3.501 7.731 15.036 1.00 0.00<br />
ATOM 4 C4 UNK 0 1 2.048 7.716 14.547 1.00 0.00<br />
ATOM 5 C5 UNK 0 1 1.242 6.570 15.071 1.00 0.00<br />
ATOM 6 C6 UNK 0 1 1.742 5.525 15.720 1.00 0.00<br />
ATOM 7 C7 UNK 0 1 0.960 4.412 16.249 1.00 0.00<br />
ATOM 8 C8 UNK 0 1 -0.096 3.785 15.688 1.00 0.00<br />
ATOM 9 C9 UNK 0 1 -0.891 2.748 16.260 1.00 0.00<br />
ATOM 10 C10 UNK 0 1 -2.039 2.359 15.656 1.00 0.00<br />
ATOM 11 C11 UNK 0 1 -2.995 1.432 16.171 1.00 0.00<br />
ATOM 12 C12 UNK 0 1 -4.118 0.952 15.603 1.00 0.00<br />
ATOM 13 C13 UNK 0 1 -4.579 1.155 14.210 1.00 0.00<br />
ATOM 14 C14 UNK 0 1 -3.772 1.162 13.168 1.00 0.00<br />
ATOM 15 C15 UNK 0 1 -4.144 1.290 11.748 1.00 0.00<br />
ATOM 16 O1 UNK 0 1 -3.417 1.200 10.832 1.00 0.00<br />
ATOM 17 C16 UNK 0 1 -0.251 6.757 14.825 1.00 0.00<br />
ATOM 18 C17 UNK 0 1 3.537 5.722 17.465 1.00 0.00<br />
ATOM 19 C18 UNK 0 1 3.755 3.989 15.704 1.00 0.00<br />
ATOM 20 C19 UNK 0 1 -0.446 2.130 17.555 1.00 0.00<br />
ATOM 21 C20 UNK 0 1 -6.097 1.275 14.125 1.00 0.00<br />
ATOM 22 H1 UNK 0 1 4.961 6.299 15.236 1.00 0.00<br />
ATOM 23 H2 UNK 0 1 4.033 6.074 13.960 1.00 0.00<br />
ATOM 24 H3 UNK 0 1 3.361 8.099 16.086 1.00 0.00<br />
ATOM 25 H4 UNK 0 1 4.112 8.346 14.368 1.00 0.00<br />
ATOM 26 H5 UNK 0 1 1.613 8.609 14.846 1.00 0.00<br />
ATOM 27 H6 UNK 0 1 2.096 8.271 13.429 1.00 0.00<br />
ATOM 28 H7 UNK 0 1 1.167 4.027 17.220 1.00 0.00<br />
ATOM 29 H8 UNK 0 1 -0.283 4.132 14.828 1.00 0.00<br />
ATOM 30 H9 UNK 0 1 -2.166 2.700 14.811 1.00 0.00<br />
ATOM 31 H10 UNK 0 1 -2.959 1.140 17.220 1.00 0.00<br />
ATOM 32 H11 UNK 0 1 -4.766 0.337 16.175 1.00 0.00<br />
ATOM 33 H12 UNK 0 1 -2.863 1.012 13.199 1.00 0.00<br />
ATOM 34 H13 UNK 0 1 -5.051 1.500 11.604 1.00 0.00<br />
ATOM 35 H14 UNK 0 1 -0.500 7.641 14.882 1.00 0.00<br />
ATOM 36 H15 UNK 0 1 -0.354 6.404 13.677 1.00 0.00<br />
ATOM 37 H16 UNK 0 1 -0.828 6.374 15.537 1.00 0.00<br />
ATOM 38 H17 UNK 0 1 4.443 5.482 17.539 1.00 0.00<br />
ATOM 39 H18 UNK 0 1 3.171 6.749 17.876 1.00 0.00<br />
ATOM 40 H19 UNK 0 1 2.971 5.092 18.159 1.00 0.00<br />
ATOM 41 H20 UNK 0 1 3.359 3.330 16.246 1.00 0.00<br />
ATOM 42 H21 UNK 0 1 3.564 3.712 14.704 1.00 0.00<br />
ATOM 43 H22 UNK 0 1 4.832 3.967 15.608 1.00 0.00<br />
ATOM 44 H23 UNK 0 1 0.526 2.025 17.433 1.00 0.00<br />
ATOM 45 H24 UNK 0 1 -0.489 2.700 18.230 1.00 0.00<br />
ATOM 46 H25 UNK 0 1 -1.006 1.387 18.000 1.00 0.00<br />
ATOM 47 H26 UNK 0 1 -6.646 0.300 14.793 1.00 0.00<br />
ATOM 48 H27 UNK 0 1 -6.440 2.100 14.580 1.00 0.00<br />
ATOM 49 H28 UNK 0 1 -6.271 1.320 13.269 1.00 0.00<br />
CONECT 1 2 6 18 19<br />
CONECT 2 1 3 22 23<br />
CONECT 3 2 4 24 25<br />
CONECT 4 3 5 26 27<br />
CONECT 5 4 6 17<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 28<br />
CONECT 8 7 9 29<br />
CONECT 9 8 10 20<br />
CONECT 10 9 11 30<br />
CONECT 11 10 12 31<br />
CONECT 12 11 13 32<br />
CONECT 13 12 14 21<br />
CONECT 14 13 15 33<br />
CONECT 15 14 16 34<br />
CONECT 16 15<br />
CONECT 17 5 35 36 37<br />
CONECT 18 1 38 39 40<br />
CONECT 19 1 41 42 43<br />
CONECT 20 9 44 45 46<br />
CONECT 21 13 47 48 49<br />
CONECT 22 2<br />
CONECT 23 2<br />
CONECT 24 3<br />
CONECT 25 3<br />
CONECT 26 4<br />
CONECT 27 4<br />
CONECT 28 7<br />
CONECT 29 8<br />
CONECT 30 10<br />
CONECT 31 11<br />
CONECT 32 12<br />
CONECT 33 14<br />
CONECT 34 15<br />
CONECT 35 17<br />
CONECT 36 17<br />
CONECT 37 17<br />
CONECT 38 18<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 19<br />
CONECT 42 19<br />
CONECT 43 19<br />
CONECT 44 20<br />
CONECT 45 20<br />
CONECT 46 20<br />
CONECT 47 21<br />
CONECT 48 21<br />
CONECT 49 21<br />
MASTER 0 0 0 0 0 0 0 0 49 0 49 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY TRETAL03<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 14.956 8.277 15.291 90.00 104.92 90.00 P 21/n 4<br />
ATOM 1 O1 UNK 0 1 9.309 3.852 9.139 1.00 0.00<br />
ATOM 2 C1 UNK 0 1 -1.723 -0.739 4.047 1.00 0.00<br />
ATOM 3 C2 UNK 0 1 -0.452 -1.316 3.444 1.00 0.00<br />
ATOM 4 C3 UNK 0 1 -2.519 -1.832 4.761 1.00 0.00<br />
ATOM 5 C4 UNK 0 1 -2.460 -0.197 2.791 1.00 0.00<br />
ATOM 6 C5 UNK 0 1 -3.484 0.764 3.073 1.00 0.00<br />
ATOM 7 C6 UNK 0 1 -3.039 1.904 3.908 1.00 0.00<br />
ATOM 8 C7 UNK 0 1 -2.002 1.579 4.954 1.00 0.00<br />
ATOM 9 C8 UNK 0 1 -1.767 2.692 5.929 1.00 0.00<br />
ATOM 10 C9 UNK 0 1 -1.402 0.397 5.000 1.00 0.00<br />
ATOM 11 C10 UNK 0 1 -0.360 0.092 6.017 1.00 0.00<br />
ATOM 12 C11 UNK 0 1 0.764 0.756 6.175 1.00 0.00<br />
ATOM 13 C12 UNK 0 1 1.826 0.493 7.151 1.00 0.00<br />
ATOM 14 C13 UNK 0 1 1.604 -0.603 8.138 1.00 0.00<br />
ATOM 15 C14 UNK 0 1 2.930 1.234 7.109 1.00 0.00<br />
ATOM 16 C15 UNK 0 1 4.081 1.142 7.980 1.00 0.00<br />
ATOM 17 C16 UNK 0 1 5.145 1.932 7.893 1.00 0.00<br />
ATOM 18 C17 UNK 0 1 6.289 1.962 8.796 1.00 0.00<br />
ATOM 19 C18 UNK 0 1 6.288 1.002 9.940 1.00 0.00<br />
ATOM 20 C19 UNK 0 1 7.263 2.851 8.564 1.00 0.00<br />
ATOM 21 C20 UNK 0 1 8.452 3.036 9.396 1.00 0.00<br />
CONECT 1 21<br />
CONECT 2 3 4 5 10<br />
CONECT 3 2<br />
CONECT 4 2<br />
CONECT 5 2 6<br />
CONECT 6 5 7<br />
CONECT 7 6 8<br />
CONECT 8 7 9 10<br />
CONECT 9 8<br />
CONECT 10 2 8 11<br />
CONECT 11 10 12<br />
CONECT 12 11 13<br />
CONECT 13 12 14 15<br />
CONECT 14 13<br />
CONECT 15 13 16<br />
CONECT 16 15 17<br />
CONECT 17 16 18<br />
CONECT 18 17 19 20<br />
CONECT 19 18<br />
CONECT 20 18 21<br />
CONECT 21 1 20<br />
MASTER 0 0 0 0 0 0 0 0 21 0 21 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
==Effects of Bunazosin on ocular circulation and retinal neuronal damage==<br />
<br />
By applying bunazosin hydrochloride into a healthy humans, it increases the blood velocity in the optic nerve head(ONH),retina and choroid, without changing either heart rate and blood pressure dramaticallt. This drug was also applied to rabbits and rats, giving positive results. These shows that bunazosin hydrochloride have improvement effect both in the ocular circulation and a direct neuroprotective effct. Therefore, it may be useful to use bunazosin hydrochloride as a therapeutic drug against retinal diseases which is associated with the ocular circulation.<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.<br />
*3.Hara, Hideaki / Ichikawa, Masaki / Oku, Hidehiro / Shimazawa, Masamitsu / Araie, Makoto, Cardiovascular drug reviews, Apr 2005</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=4989
It:Retinal
2006-11-07T11:47:05Z
<p>So105: /* Structure of all-trans retinal */minor change</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''', also known as retinaldehyde or retinene<sub>1</sub> is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="1" bgcolor="lt blue"|<br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Cis-Retinal''' <br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Trans-Retinal''' <br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''<br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''<br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)<br />
=C(C)CCC1<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)<br />
=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
|[[Image:AllTransRetinal.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY BOKSEZ<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 14.761 8.292 15.210 90.00 102.40 90.00 P 21/n 4<br />
ATOM 1 O1 UNK 0 1 8.800 1.137 3.735 1.00 0.00<br />
ATOM 2 O2 UNK 0 1 -3.642 0.109 -1.855 1.00 0.00<br />
ATOM 3 C1 UNK 0 1 7.236 4.986 3.316 1.00 0.00<br />
ATOM 4 C2 UNK 0 1 7.808 4.433 4.641 1.00 0.00<br />
ATOM 5 C3 UNK 0 1 8.881 3.407 4.434 1.00 0.00<br />
ATOM 6 C4 UNK 0 1 8.402 2.292 3.586 1.00 0.00<br />
ATOM 7 C5 UNK 0 1 7.434 2.593 2.496 1.00 0.00<br />
ATOM 8 C6 UNK 0 1 6.851 3.816 2.410 1.00 0.00<br />
ATOM 9 C7 UNK 0 1 5.849 4.111 1.365 1.00 0.00<br />
ATOM 10 C8 UNK 0 1 4.735 3.412 1.188 1.00 0.00<br />
ATOM 11 C9 UNK 0 1 3.695 3.741 0.202 1.00 0.00<br />
ATOM 12 C10 UNK 0 1 2.601 2.943 0.227 1.00 0.00<br />
ATOM 13 C11 UNK 0 1 1.409 3.020 -0.654 1.00 0.00<br />
ATOM 14 C12 UNK 0 1 0.394 2.212 -0.535 1.00 0.00<br />
ATOM 15 C13 UNK 0 1 -0.769 2.174 -1.450 1.00 0.00<br />
ATOM 16 C14 UNK 0 1 -1.684 1.256 -1.236 1.00 0.00<br />
ATOM 17 C15 UNK 0 1 -2.881 0.999 -2.043 1.00 0.00<br />
ATOM 18 C16 UNK 0 1 7.167 1.427 1.567 1.00 0.00<br />
ATOM 19 C17 UNK 0 1 5.974 5.755 3.760 1.00 0.00<br />
ATOM 20 C18 UNK 0 1 8.204 5.906 2.607 1.00 0.00<br />
ATOM 21 C19 UNK 0 1 3.919 4.853 -0.787 1.00 0.00<br />
ATOM 22 C20 UNK 0 1 -0.796 3.178 -2.557 1.00 0.00<br />
ATOM 23 H1 UNK 0 1 6.939 4.113 5.229 1.00 0.00<br />
ATOM 24 H2 UNK 0 1 8.383 5.232 5.110 1.00 0.00<br />
ATOM 25 H3 UNK 0 1 9.085 3.458 5.274 1.00 0.00<br />
ATOM 26 H4 UNK 0 1 9.452 3.930 3.803 1.00 0.00<br />
ATOM 27 H5 UNK 0 1 6.133 4.784 0.772 1.00 0.00<br />
ATOM 28 H6 UNK 0 1 4.476 2.728 1.797 1.00 0.00<br />
ATOM 29 H7 UNK 0 1 2.453 2.222 0.995 1.00 0.00<br />
ATOM 30 H8 UNK 0 1 1.583 3.856 -1.292 1.00 0.00<br />
ATOM 31 H9 UNK 0 1 0.154 1.750 0.238 1.00 0.00<br />
ATOM 32 H10 UNK 0 1 -1.746 0.871 -0.520 1.00 0.00<br />
ATOM 33 H11 UNK 0 1 -2.722 1.857 -2.659 1.00 0.00<br />
ATOM 34 H12 UNK 0 1 5.584 6.194 3.134 1.00 0.00<br />
ATOM 35 H13 UNK 0 1 5.249 5.174 4.323 1.00 0.00<br />
ATOM 36 H14 UNK 0 1 6.345 6.509 4.442 1.00 0.00<br />
ATOM 37 H15 UNK 0 1 7.632 6.136 2.080 1.00 0.00<br />
ATOM 38 H16 UNK 0 1 9.036 5.224 2.674 1.00 0.00<br />
ATOM 39 H17 UNK 0 1 8.192 0.796 1.411 1.00 0.00<br />
ATOM 40 H18 UNK 0 1 6.845 1.683 0.891 1.00 0.00<br />
ATOM 41 H19 UNK 0 1 6.601 0.730 1.664 1.00 0.00<br />
ATOM 42 H20 UNK 0 1 3.287 5.000 -1.055 1.00 0.00<br />
ATOM 43 H21 UNK 0 1 3.641 5.431 -0.312 1.00 0.00<br />
ATOM 44 H22 UNK 0 1 4.744 4.677 -1.233 1.00 0.00<br />
ATOM 45 H23 UNK 0 1 -1.169 2.952 -3.075 1.00 0.00<br />
ATOM 46 H24 UNK 0 1 -1.270 3.988 -2.080 1.00 0.00<br />
ATOM 47 H25 UNK 0 1 -0.054 3.018 -3.313 1.00 0.00<br />
CONECT 1 6<br />
CONECT 2 17<br />
CONECT 3 4 8 19 20<br />
CONECT 4 3 5 23 24<br />
CONECT 5 4 6 25 26<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 18<br />
CONECT 8 3 7 9<br />
CONECT 9 8 10 27<br />
CONECT 10 9 11 28<br />
CONECT 11 10 12 21<br />
CONECT 12 11 13 29<br />
CONECT 13 12 14 30<br />
CONECT 14 13 15 31<br />
CONECT 15 14 16 22<br />
CONECT 16 15 17 32<br />
CONECT 17 2 16 33<br />
CONECT 18 7 39 40 41<br />
CONECT 19 3 34 35 36<br />
CONECT 20 3 37 38<br />
CONECT 21 11 42 43 44<br />
CONECT 22 15 45 46 47<br />
CONECT 23 4<br />
CONECT 24 4<br />
CONECT 25 5<br />
CONECT 26 5<br />
CONECT 27 9<br />
CONECT 28 10<br />
CONECT 29 12<br />
CONECT 30 13<br />
CONECT 31 14<br />
CONECT 32 16<br />
CONECT 33 17<br />
CONECT 34 19<br />
CONECT 35 19<br />
CONECT 36 19<br />
CONECT 37 20<br />
CONECT 38 20<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 18<br />
CONECT 42 21<br />
CONECT 43 21<br />
CONECT 44 21<br />
CONECT 45 22<br />
CONECT 46 22<br />
CONECT 47 22<br />
MASTER 0 0 0 0 0 0 0 0 47 0 47 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="2" bgcolor=""|[http://www.ch.ic.ac.uk/wiki/index.php/Image:Trans-retinal.cdx ChemDraw 3D structure]<br />
|}<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br>Compound A 3D Picture<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY CRETAL01<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 13.180 7.499 17.803 90.00 95.66 90.00 P 21/n 4<br />
ATOM 1 C1 UNK 0 1 3.279 5.402 15.975 1.00 0.00<br />
ATOM 2 C2 UNK 0 1 4.046 6.337 15.055 1.00 0.00<br />
ATOM 3 C3 UNK 0 1 3.501 7.731 15.036 1.00 0.00<br />
ATOM 4 C4 UNK 0 1 2.048 7.716 14.547 1.00 0.00<br />
ATOM 5 C5 UNK 0 1 1.242 6.570 15.071 1.00 0.00<br />
ATOM 6 C6 UNK 0 1 1.742 5.525 15.720 1.00 0.00<br />
ATOM 7 C7 UNK 0 1 0.960 4.412 16.249 1.00 0.00<br />
ATOM 8 C8 UNK 0 1 -0.096 3.785 15.688 1.00 0.00<br />
ATOM 9 C9 UNK 0 1 -0.891 2.748 16.260 1.00 0.00<br />
ATOM 10 C10 UNK 0 1 -2.039 2.359 15.656 1.00 0.00<br />
ATOM 11 C11 UNK 0 1 -2.995 1.432 16.171 1.00 0.00<br />
ATOM 12 C12 UNK 0 1 -4.118 0.952 15.603 1.00 0.00<br />
ATOM 13 C13 UNK 0 1 -4.579 1.155 14.210 1.00 0.00<br />
ATOM 14 C14 UNK 0 1 -3.772 1.162 13.168 1.00 0.00<br />
ATOM 15 C15 UNK 0 1 -4.144 1.290 11.748 1.00 0.00<br />
ATOM 16 O1 UNK 0 1 -3.417 1.200 10.832 1.00 0.00<br />
ATOM 17 C16 UNK 0 1 -0.251 6.757 14.825 1.00 0.00<br />
ATOM 18 C17 UNK 0 1 3.537 5.722 17.465 1.00 0.00<br />
ATOM 19 C18 UNK 0 1 3.755 3.989 15.704 1.00 0.00<br />
ATOM 20 C19 UNK 0 1 -0.446 2.130 17.555 1.00 0.00<br />
ATOM 21 C20 UNK 0 1 -6.097 1.275 14.125 1.00 0.00<br />
ATOM 22 H1 UNK 0 1 4.961 6.299 15.236 1.00 0.00<br />
ATOM 23 H2 UNK 0 1 4.033 6.074 13.960 1.00 0.00<br />
ATOM 24 H3 UNK 0 1 3.361 8.099 16.086 1.00 0.00<br />
ATOM 25 H4 UNK 0 1 4.112 8.346 14.368 1.00 0.00<br />
ATOM 26 H5 UNK 0 1 1.613 8.609 14.846 1.00 0.00<br />
ATOM 27 H6 UNK 0 1 2.096 8.271 13.429 1.00 0.00<br />
ATOM 28 H7 UNK 0 1 1.167 4.027 17.220 1.00 0.00<br />
ATOM 29 H8 UNK 0 1 -0.283 4.132 14.828 1.00 0.00<br />
ATOM 30 H9 UNK 0 1 -2.166 2.700 14.811 1.00 0.00<br />
ATOM 31 H10 UNK 0 1 -2.959 1.140 17.220 1.00 0.00<br />
ATOM 32 H11 UNK 0 1 -4.766 0.337 16.175 1.00 0.00<br />
ATOM 33 H12 UNK 0 1 -2.863 1.012 13.199 1.00 0.00<br />
ATOM 34 H13 UNK 0 1 -5.051 1.500 11.604 1.00 0.00<br />
ATOM 35 H14 UNK 0 1 -0.500 7.641 14.882 1.00 0.00<br />
ATOM 36 H15 UNK 0 1 -0.354 6.404 13.677 1.00 0.00<br />
ATOM 37 H16 UNK 0 1 -0.828 6.374 15.537 1.00 0.00<br />
ATOM 38 H17 UNK 0 1 4.443 5.482 17.539 1.00 0.00<br />
ATOM 39 H18 UNK 0 1 3.171 6.749 17.876 1.00 0.00<br />
ATOM 40 H19 UNK 0 1 2.971 5.092 18.159 1.00 0.00<br />
ATOM 41 H20 UNK 0 1 3.359 3.330 16.246 1.00 0.00<br />
ATOM 42 H21 UNK 0 1 3.564 3.712 14.704 1.00 0.00<br />
ATOM 43 H22 UNK 0 1 4.832 3.967 15.608 1.00 0.00<br />
ATOM 44 H23 UNK 0 1 0.526 2.025 17.433 1.00 0.00<br />
ATOM 45 H24 UNK 0 1 -0.489 2.700 18.230 1.00 0.00<br />
ATOM 46 H25 UNK 0 1 -1.006 1.387 18.000 1.00 0.00<br />
ATOM 47 H26 UNK 0 1 -6.646 0.300 14.793 1.00 0.00<br />
ATOM 48 H27 UNK 0 1 -6.440 2.100 14.580 1.00 0.00<br />
ATOM 49 H28 UNK 0 1 -6.271 1.320 13.269 1.00 0.00<br />
CONECT 1 2 6 18 19<br />
CONECT 2 1 3 22 23<br />
CONECT 3 2 4 24 25<br />
CONECT 4 3 5 26 27<br />
CONECT 5 4 6 17<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 28<br />
CONECT 8 7 9 29<br />
CONECT 9 8 10 20<br />
CONECT 10 9 11 30<br />
CONECT 11 10 12 31<br />
CONECT 12 11 13 32<br />
CONECT 13 12 14 21<br />
CONECT 14 13 15 33<br />
CONECT 15 14 16 34<br />
CONECT 16 15<br />
CONECT 17 5 35 36 37<br />
CONECT 18 1 38 39 40<br />
CONECT 19 1 41 42 43<br />
CONECT 20 9 44 45 46<br />
CONECT 21 13 47 48 49<br />
CONECT 22 2<br />
CONECT 23 2<br />
CONECT 24 3<br />
CONECT 25 3<br />
CONECT 26 4<br />
CONECT 27 4<br />
CONECT 28 7<br />
CONECT 29 8<br />
CONECT 30 10<br />
CONECT 31 11<br />
CONECT 32 12<br />
CONECT 33 14<br />
CONECT 34 15<br />
CONECT 35 17<br />
CONECT 36 17<br />
CONECT 37 17<br />
CONECT 38 18<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 19<br />
CONECT 42 19<br />
CONECT 43 19<br />
CONECT 44 20<br />
CONECT 45 20<br />
CONECT 46 20<br />
CONECT 47 21<br />
CONECT 48 21<br />
CONECT 49 21<br />
MASTER 0 0 0 0 0 0 0 0 49 0 49 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
Compound B 3D picture<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY TRETAL03<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 14.956 8.277 15.291 90.00 104.92 90.00 P 21/n 4<br />
ATOM 1 O1 UNK 0 1 9.309 3.852 9.139 1.00 0.00<br />
ATOM 2 C1 UNK 0 1 -1.723 -0.739 4.047 1.00 0.00<br />
ATOM 3 C2 UNK 0 1 -0.452 -1.316 3.444 1.00 0.00<br />
ATOM 4 C3 UNK 0 1 -2.519 -1.832 4.761 1.00 0.00<br />
ATOM 5 C4 UNK 0 1 -2.460 -0.197 2.791 1.00 0.00<br />
ATOM 6 C5 UNK 0 1 -3.484 0.764 3.073 1.00 0.00<br />
ATOM 7 C6 UNK 0 1 -3.039 1.904 3.908 1.00 0.00<br />
ATOM 8 C7 UNK 0 1 -2.002 1.579 4.954 1.00 0.00<br />
ATOM 9 C8 UNK 0 1 -1.767 2.692 5.929 1.00 0.00<br />
ATOM 10 C9 UNK 0 1 -1.402 0.397 5.000 1.00 0.00<br />
ATOM 11 C10 UNK 0 1 -0.360 0.092 6.017 1.00 0.00<br />
ATOM 12 C11 UNK 0 1 0.764 0.756 6.175 1.00 0.00<br />
ATOM 13 C12 UNK 0 1 1.826 0.493 7.151 1.00 0.00<br />
ATOM 14 C13 UNK 0 1 1.604 -0.603 8.138 1.00 0.00<br />
ATOM 15 C14 UNK 0 1 2.930 1.234 7.109 1.00 0.00<br />
ATOM 16 C15 UNK 0 1 4.081 1.142 7.980 1.00 0.00<br />
ATOM 17 C16 UNK 0 1 5.145 1.932 7.893 1.00 0.00<br />
ATOM 18 C17 UNK 0 1 6.289 1.962 8.796 1.00 0.00<br />
ATOM 19 C18 UNK 0 1 6.288 1.002 9.940 1.00 0.00<br />
ATOM 20 C19 UNK 0 1 7.263 2.851 8.564 1.00 0.00<br />
ATOM 21 C20 UNK 0 1 8.452 3.036 9.396 1.00 0.00<br />
CONECT 1 21<br />
CONECT 2 3 4 5 10<br />
CONECT 3 2<br />
CONECT 4 2<br />
CONECT 5 2 6<br />
CONECT 6 5 7<br />
CONECT 7 6 8<br />
CONECT 8 7 9 10<br />
CONECT 9 8<br />
CONECT 10 2 8 11<br />
CONECT 11 10 12<br />
CONECT 12 11 13<br />
CONECT 13 12 14 15<br />
CONECT 14 13<br />
CONECT 15 13 16<br />
CONECT 16 15 17<br />
CONECT 17 16 18<br />
CONECT 18 17 19 20<br />
CONECT 19 18<br />
CONECT 20 18 21<br />
CONECT 21 1 20<br />
MASTER 0 0 0 0 0 0 0 0 21 0 21 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
==Effects of Bunazosin on ocular circulation and retinal neuronal damage==<br />
<br />
By applying bunazosin hydrochloride into a healthy humans, it increases the blood velocity in the optic nerve head(ONH),retina and choroid, without changing either heart rate and blood pressure dramaticallt. This drug was also applied to rabbits and rats, giving positive results. These shows that bunazosin hydrochloride have improvement effect both in the ocular circulation and a direct neuroprotective effct. Therefore, it may be useful to use bunazosin hydrochloride as a therapeutic drug against retinal diseases which is associated with the ocular circulation.<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.<br />
*3.Hara, Hideaki / Ichikawa, Masaki / Oku, Hidehiro / Shimazawa, Masamitsu / Araie, Makoto, Cardiovascular drug reviews, Apr 2005</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=4988
It:Retinal
2006-11-07T11:44:43Z
<p>So105: /* Structure of all-trans retinal */ changed render on molecule to bns</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''', also known as retinaldehyde or retinene<sub>1</sub> is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="1" bgcolor="lt blue"|<br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Cis-Retinal''' <br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Trans-Retinal''' <br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''<br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''<br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)<br />
=C(C)CCC1<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)<br />
=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
|[[Image:AllTransRetinal.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY BOKSEZ<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 14.761 8.292 15.210 90.00 102.40 90.00 P 21/n 4<br />
ATOM 1 O1 UNK 0 1 8.800 1.137 3.735 1.00 0.00<br />
ATOM 2 O2 UNK 0 1 -3.642 0.109 -1.855 1.00 0.00<br />
ATOM 3 C1 UNK 0 1 7.236 4.986 3.316 1.00 0.00<br />
ATOM 4 C2 UNK 0 1 7.808 4.433 4.641 1.00 0.00<br />
ATOM 5 C3 UNK 0 1 8.881 3.407 4.434 1.00 0.00<br />
ATOM 6 C4 UNK 0 1 8.402 2.292 3.586 1.00 0.00<br />
ATOM 7 C5 UNK 0 1 7.434 2.593 2.496 1.00 0.00<br />
ATOM 8 C6 UNK 0 1 6.851 3.816 2.410 1.00 0.00<br />
ATOM 9 C7 UNK 0 1 5.849 4.111 1.365 1.00 0.00<br />
ATOM 10 C8 UNK 0 1 4.735 3.412 1.188 1.00 0.00<br />
ATOM 11 C9 UNK 0 1 3.695 3.741 0.202 1.00 0.00<br />
ATOM 12 C10 UNK 0 1 2.601 2.943 0.227 1.00 0.00<br />
ATOM 13 C11 UNK 0 1 1.409 3.020 -0.654 1.00 0.00<br />
ATOM 14 C12 UNK 0 1 0.394 2.212 -0.535 1.00 0.00<br />
ATOM 15 C13 UNK 0 1 -0.769 2.174 -1.450 1.00 0.00<br />
ATOM 16 C14 UNK 0 1 -1.684 1.256 -1.236 1.00 0.00<br />
ATOM 17 C15 UNK 0 1 -2.881 0.999 -2.043 1.00 0.00<br />
ATOM 18 C16 UNK 0 1 7.167 1.427 1.567 1.00 0.00<br />
ATOM 19 C17 UNK 0 1 5.974 5.755 3.760 1.00 0.00<br />
ATOM 20 C18 UNK 0 1 8.204 5.906 2.607 1.00 0.00<br />
ATOM 21 C19 UNK 0 1 3.919 4.853 -0.787 1.00 0.00<br />
ATOM 22 C20 UNK 0 1 -0.796 3.178 -2.557 1.00 0.00<br />
ATOM 23 H1 UNK 0 1 6.939 4.113 5.229 1.00 0.00<br />
ATOM 24 H2 UNK 0 1 8.383 5.232 5.110 1.00 0.00<br />
ATOM 25 H3 UNK 0 1 9.085 3.458 5.274 1.00 0.00<br />
ATOM 26 H4 UNK 0 1 9.452 3.930 3.803 1.00 0.00<br />
ATOM 27 H5 UNK 0 1 6.133 4.784 0.772 1.00 0.00<br />
ATOM 28 H6 UNK 0 1 4.476 2.728 1.797 1.00 0.00<br />
ATOM 29 H7 UNK 0 1 2.453 2.222 0.995 1.00 0.00<br />
ATOM 30 H8 UNK 0 1 1.583 3.856 -1.292 1.00 0.00<br />
ATOM 31 H9 UNK 0 1 0.154 1.750 0.238 1.00 0.00<br />
ATOM 32 H10 UNK 0 1 -1.746 0.871 -0.520 1.00 0.00<br />
ATOM 33 H11 UNK 0 1 -2.722 1.857 -2.659 1.00 0.00<br />
ATOM 34 H12 UNK 0 1 5.584 6.194 3.134 1.00 0.00<br />
ATOM 35 H13 UNK 0 1 5.249 5.174 4.323 1.00 0.00<br />
ATOM 36 H14 UNK 0 1 6.345 6.509 4.442 1.00 0.00<br />
ATOM 37 H15 UNK 0 1 7.632 6.136 2.080 1.00 0.00<br />
ATOM 38 H16 UNK 0 1 9.036 5.224 2.674 1.00 0.00<br />
ATOM 39 H17 UNK 0 1 8.192 0.796 1.411 1.00 0.00<br />
ATOM 40 H18 UNK 0 1 6.845 1.683 0.891 1.00 0.00<br />
ATOM 41 H19 UNK 0 1 6.601 0.730 1.664 1.00 0.00<br />
ATOM 42 H20 UNK 0 1 3.287 5.000 -1.055 1.00 0.00<br />
ATOM 43 H21 UNK 0 1 3.641 5.431 -0.312 1.00 0.00<br />
ATOM 44 H22 UNK 0 1 4.744 4.677 -1.233 1.00 0.00<br />
ATOM 45 H23 UNK 0 1 -1.169 2.952 -3.075 1.00 0.00<br />
ATOM 46 H24 UNK 0 1 -1.270 3.988 -2.080 1.00 0.00<br />
ATOM 47 H25 UNK 0 1 -0.054 3.018 -3.313 1.00 0.00<br />
CONECT 1 6<br />
CONECT 2 17<br />
CONECT 3 4 8 19 20<br />
CONECT 4 3 5 23 24<br />
CONECT 5 4 6 25 26<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 18<br />
CONECT 8 3 7 9<br />
CONECT 9 8 10 27<br />
CONECT 10 9 11 28<br />
CONECT 11 10 12 21<br />
CONECT 12 11 13 29<br />
CONECT 13 12 14 30<br />
CONECT 14 13 15 31<br />
CONECT 15 14 16 22<br />
CONECT 16 15 17 32<br />
CONECT 17 2 16 33<br />
CONECT 18 7 39 40 41<br />
CONECT 19 3 34 35 36<br />
CONECT 20 3 37 38<br />
CONECT 21 11 42 43 44<br />
CONECT 22 15 45 46 47<br />
CONECT 23 4<br />
CONECT 24 4<br />
CONECT 25 5<br />
CONECT 26 5<br />
CONECT 27 9<br />
CONECT 28 10<br />
CONECT 29 12<br />
CONECT 30 13<br />
CONECT 31 14<br />
CONECT 32 16<br />
CONECT 33 17<br />
CONECT 34 19<br />
CONECT 35 19<br />
CONECT 36 19<br />
CONECT 37 20<br />
CONECT 38 20<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 18<br />
CONECT 42 21<br />
CONECT 43 21<br />
CONECT 44 21<br />
CONECT 45 22<br />
CONECT 46 22<br />
CONECT 47 22<br />
MASTER 0 0 0 0 0 0 0 0 47 0 47 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|[http://www.ch.ic.ac.uk/wiki/index.php/Image:Trans-retinal.cdx ChemDraw 3D structure]<br />
|}<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br>Compound A 3D Picture<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY CRETAL01<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 13.180 7.499 17.803 90.00 95.66 90.00 P 21/n 4<br />
ATOM 1 C1 UNK 0 1 3.279 5.402 15.975 1.00 0.00<br />
ATOM 2 C2 UNK 0 1 4.046 6.337 15.055 1.00 0.00<br />
ATOM 3 C3 UNK 0 1 3.501 7.731 15.036 1.00 0.00<br />
ATOM 4 C4 UNK 0 1 2.048 7.716 14.547 1.00 0.00<br />
ATOM 5 C5 UNK 0 1 1.242 6.570 15.071 1.00 0.00<br />
ATOM 6 C6 UNK 0 1 1.742 5.525 15.720 1.00 0.00<br />
ATOM 7 C7 UNK 0 1 0.960 4.412 16.249 1.00 0.00<br />
ATOM 8 C8 UNK 0 1 -0.096 3.785 15.688 1.00 0.00<br />
ATOM 9 C9 UNK 0 1 -0.891 2.748 16.260 1.00 0.00<br />
ATOM 10 C10 UNK 0 1 -2.039 2.359 15.656 1.00 0.00<br />
ATOM 11 C11 UNK 0 1 -2.995 1.432 16.171 1.00 0.00<br />
ATOM 12 C12 UNK 0 1 -4.118 0.952 15.603 1.00 0.00<br />
ATOM 13 C13 UNK 0 1 -4.579 1.155 14.210 1.00 0.00<br />
ATOM 14 C14 UNK 0 1 -3.772 1.162 13.168 1.00 0.00<br />
ATOM 15 C15 UNK 0 1 -4.144 1.290 11.748 1.00 0.00<br />
ATOM 16 O1 UNK 0 1 -3.417 1.200 10.832 1.00 0.00<br />
ATOM 17 C16 UNK 0 1 -0.251 6.757 14.825 1.00 0.00<br />
ATOM 18 C17 UNK 0 1 3.537 5.722 17.465 1.00 0.00<br />
ATOM 19 C18 UNK 0 1 3.755 3.989 15.704 1.00 0.00<br />
ATOM 20 C19 UNK 0 1 -0.446 2.130 17.555 1.00 0.00<br />
ATOM 21 C20 UNK 0 1 -6.097 1.275 14.125 1.00 0.00<br />
ATOM 22 H1 UNK 0 1 4.961 6.299 15.236 1.00 0.00<br />
ATOM 23 H2 UNK 0 1 4.033 6.074 13.960 1.00 0.00<br />
ATOM 24 H3 UNK 0 1 3.361 8.099 16.086 1.00 0.00<br />
ATOM 25 H4 UNK 0 1 4.112 8.346 14.368 1.00 0.00<br />
ATOM 26 H5 UNK 0 1 1.613 8.609 14.846 1.00 0.00<br />
ATOM 27 H6 UNK 0 1 2.096 8.271 13.429 1.00 0.00<br />
ATOM 28 H7 UNK 0 1 1.167 4.027 17.220 1.00 0.00<br />
ATOM 29 H8 UNK 0 1 -0.283 4.132 14.828 1.00 0.00<br />
ATOM 30 H9 UNK 0 1 -2.166 2.700 14.811 1.00 0.00<br />
ATOM 31 H10 UNK 0 1 -2.959 1.140 17.220 1.00 0.00<br />
ATOM 32 H11 UNK 0 1 -4.766 0.337 16.175 1.00 0.00<br />
ATOM 33 H12 UNK 0 1 -2.863 1.012 13.199 1.00 0.00<br />
ATOM 34 H13 UNK 0 1 -5.051 1.500 11.604 1.00 0.00<br />
ATOM 35 H14 UNK 0 1 -0.500 7.641 14.882 1.00 0.00<br />
ATOM 36 H15 UNK 0 1 -0.354 6.404 13.677 1.00 0.00<br />
ATOM 37 H16 UNK 0 1 -0.828 6.374 15.537 1.00 0.00<br />
ATOM 38 H17 UNK 0 1 4.443 5.482 17.539 1.00 0.00<br />
ATOM 39 H18 UNK 0 1 3.171 6.749 17.876 1.00 0.00<br />
ATOM 40 H19 UNK 0 1 2.971 5.092 18.159 1.00 0.00<br />
ATOM 41 H20 UNK 0 1 3.359 3.330 16.246 1.00 0.00<br />
ATOM 42 H21 UNK 0 1 3.564 3.712 14.704 1.00 0.00<br />
ATOM 43 H22 UNK 0 1 4.832 3.967 15.608 1.00 0.00<br />
ATOM 44 H23 UNK 0 1 0.526 2.025 17.433 1.00 0.00<br />
ATOM 45 H24 UNK 0 1 -0.489 2.700 18.230 1.00 0.00<br />
ATOM 46 H25 UNK 0 1 -1.006 1.387 18.000 1.00 0.00<br />
ATOM 47 H26 UNK 0 1 -6.646 0.300 14.793 1.00 0.00<br />
ATOM 48 H27 UNK 0 1 -6.440 2.100 14.580 1.00 0.00<br />
ATOM 49 H28 UNK 0 1 -6.271 1.320 13.269 1.00 0.00<br />
CONECT 1 2 6 18 19<br />
CONECT 2 1 3 22 23<br />
CONECT 3 2 4 24 25<br />
CONECT 4 3 5 26 27<br />
CONECT 5 4 6 17<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 28<br />
CONECT 8 7 9 29<br />
CONECT 9 8 10 20<br />
CONECT 10 9 11 30<br />
CONECT 11 10 12 31<br />
CONECT 12 11 13 32<br />
CONECT 13 12 14 21<br />
CONECT 14 13 15 33<br />
CONECT 15 14 16 34<br />
CONECT 16 15<br />
CONECT 17 5 35 36 37<br />
CONECT 18 1 38 39 40<br />
CONECT 19 1 41 42 43<br />
CONECT 20 9 44 45 46<br />
CONECT 21 13 47 48 49<br />
CONECT 22 2<br />
CONECT 23 2<br />
CONECT 24 3<br />
CONECT 25 3<br />
CONECT 26 4<br />
CONECT 27 4<br />
CONECT 28 7<br />
CONECT 29 8<br />
CONECT 30 10<br />
CONECT 31 11<br />
CONECT 32 12<br />
CONECT 33 14<br />
CONECT 34 15<br />
CONECT 35 17<br />
CONECT 36 17<br />
CONECT 37 17<br />
CONECT 38 18<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 19<br />
CONECT 42 19<br />
CONECT 43 19<br />
CONECT 44 20<br />
CONECT 45 20<br />
CONECT 46 20<br />
CONECT 47 21<br />
CONECT 48 21<br />
CONECT 49 21<br />
MASTER 0 0 0 0 0 0 0 0 49 0 49 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
Compound B 3D picture<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY TRETAL03<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 14.956 8.277 15.291 90.00 104.92 90.00 P 21/n 4<br />
ATOM 1 O1 UNK 0 1 9.309 3.852 9.139 1.00 0.00<br />
ATOM 2 C1 UNK 0 1 -1.723 -0.739 4.047 1.00 0.00<br />
ATOM 3 C2 UNK 0 1 -0.452 -1.316 3.444 1.00 0.00<br />
ATOM 4 C3 UNK 0 1 -2.519 -1.832 4.761 1.00 0.00<br />
ATOM 5 C4 UNK 0 1 -2.460 -0.197 2.791 1.00 0.00<br />
ATOM 6 C5 UNK 0 1 -3.484 0.764 3.073 1.00 0.00<br />
ATOM 7 C6 UNK 0 1 -3.039 1.904 3.908 1.00 0.00<br />
ATOM 8 C7 UNK 0 1 -2.002 1.579 4.954 1.00 0.00<br />
ATOM 9 C8 UNK 0 1 -1.767 2.692 5.929 1.00 0.00<br />
ATOM 10 C9 UNK 0 1 -1.402 0.397 5.000 1.00 0.00<br />
ATOM 11 C10 UNK 0 1 -0.360 0.092 6.017 1.00 0.00<br />
ATOM 12 C11 UNK 0 1 0.764 0.756 6.175 1.00 0.00<br />
ATOM 13 C12 UNK 0 1 1.826 0.493 7.151 1.00 0.00<br />
ATOM 14 C13 UNK 0 1 1.604 -0.603 8.138 1.00 0.00<br />
ATOM 15 C14 UNK 0 1 2.930 1.234 7.109 1.00 0.00<br />
ATOM 16 C15 UNK 0 1 4.081 1.142 7.980 1.00 0.00<br />
ATOM 17 C16 UNK 0 1 5.145 1.932 7.893 1.00 0.00<br />
ATOM 18 C17 UNK 0 1 6.289 1.962 8.796 1.00 0.00<br />
ATOM 19 C18 UNK 0 1 6.288 1.002 9.940 1.00 0.00<br />
ATOM 20 C19 UNK 0 1 7.263 2.851 8.564 1.00 0.00<br />
ATOM 21 C20 UNK 0 1 8.452 3.036 9.396 1.00 0.00<br />
CONECT 1 21<br />
CONECT 2 3 4 5 10<br />
CONECT 3 2<br />
CONECT 4 2<br />
CONECT 5 2 6<br />
CONECT 6 5 7<br />
CONECT 7 6 8<br />
CONECT 8 7 9 10<br />
CONECT 9 8<br />
CONECT 10 2 8 11<br />
CONECT 11 10 12<br />
CONECT 12 11 13<br />
CONECT 13 12 14 15<br />
CONECT 14 13<br />
CONECT 15 13 16<br />
CONECT 16 15 17<br />
CONECT 17 16 18<br />
CONECT 18 17 19 20<br />
CONECT 19 18<br />
CONECT 20 18 21<br />
CONECT 21 1 20<br />
MASTER 0 0 0 0 0 0 0 0 21 0 21 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
==Effects of Bunazosin on ocular circulation and retinal neuronal damage==<br />
<br />
By applying bunazosin hydrochloride into a healthy humans, it increases the blood velocity in the optic nerve head(ONH),retina and choroid, without changing either heart rate and blood pressure dramaticallt. This drug was also applied to rabbits and rats, giving positive results. These shows that bunazosin hydrochloride have improvement effect both in the ocular circulation and a direct neuroprotective effct. Therefore, it may be useful to use bunazosin hydrochloride as a therapeutic drug against retinal diseases which is associated with the ocular circulation.<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.<br />
*3.Hara, Hideaki / Ichikawa, Masaki / Oku, Hidehiro / Shimazawa, Masamitsu / Araie, Makoto, Cardiovascular drug reviews, Apr 2005</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=4987
It:Retinal
2006-11-07T11:43:32Z
<p>So105: /* Structure of all-trans retinal */ changed layout</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''', also known as retinaldehyde or retinene<sub>1</sub> is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="1" bgcolor="lt blue"|<br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Cis-Retinal''' <br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Trans-Retinal''' <br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''<br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''<br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)<br />
=C(C)CCC1<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)<br />
=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
|[[Image:AllTransRetinal.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY BOKSEZ<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 14.761 8.292 15.210 90.00 102.40 90.00 P 21/n 4<br />
ATOM 1 O1 UNK 0 1 8.800 1.137 3.735 1.00 0.00<br />
ATOM 2 O2 UNK 0 1 -3.642 0.109 -1.855 1.00 0.00<br />
ATOM 3 C1 UNK 0 1 7.236 4.986 3.316 1.00 0.00<br />
ATOM 4 C2 UNK 0 1 7.808 4.433 4.641 1.00 0.00<br />
ATOM 5 C3 UNK 0 1 8.881 3.407 4.434 1.00 0.00<br />
ATOM 6 C4 UNK 0 1 8.402 2.292 3.586 1.00 0.00<br />
ATOM 7 C5 UNK 0 1 7.434 2.593 2.496 1.00 0.00<br />
ATOM 8 C6 UNK 0 1 6.851 3.816 2.410 1.00 0.00<br />
ATOM 9 C7 UNK 0 1 5.849 4.111 1.365 1.00 0.00<br />
ATOM 10 C8 UNK 0 1 4.735 3.412 1.188 1.00 0.00<br />
ATOM 11 C9 UNK 0 1 3.695 3.741 0.202 1.00 0.00<br />
ATOM 12 C10 UNK 0 1 2.601 2.943 0.227 1.00 0.00<br />
ATOM 13 C11 UNK 0 1 1.409 3.020 -0.654 1.00 0.00<br />
ATOM 14 C12 UNK 0 1 0.394 2.212 -0.535 1.00 0.00<br />
ATOM 15 C13 UNK 0 1 -0.769 2.174 -1.450 1.00 0.00<br />
ATOM 16 C14 UNK 0 1 -1.684 1.256 -1.236 1.00 0.00<br />
ATOM 17 C15 UNK 0 1 -2.881 0.999 -2.043 1.00 0.00<br />
ATOM 18 C16 UNK 0 1 7.167 1.427 1.567 1.00 0.00<br />
ATOM 19 C17 UNK 0 1 5.974 5.755 3.760 1.00 0.00<br />
ATOM 20 C18 UNK 0 1 8.204 5.906 2.607 1.00 0.00<br />
ATOM 21 C19 UNK 0 1 3.919 4.853 -0.787 1.00 0.00<br />
ATOM 22 C20 UNK 0 1 -0.796 3.178 -2.557 1.00 0.00<br />
ATOM 23 H1 UNK 0 1 6.939 4.113 5.229 1.00 0.00<br />
ATOM 24 H2 UNK 0 1 8.383 5.232 5.110 1.00 0.00<br />
ATOM 25 H3 UNK 0 1 9.085 3.458 5.274 1.00 0.00<br />
ATOM 26 H4 UNK 0 1 9.452 3.930 3.803 1.00 0.00<br />
ATOM 27 H5 UNK 0 1 6.133 4.784 0.772 1.00 0.00<br />
ATOM 28 H6 UNK 0 1 4.476 2.728 1.797 1.00 0.00<br />
ATOM 29 H7 UNK 0 1 2.453 2.222 0.995 1.00 0.00<br />
ATOM 30 H8 UNK 0 1 1.583 3.856 -1.292 1.00 0.00<br />
ATOM 31 H9 UNK 0 1 0.154 1.750 0.238 1.00 0.00<br />
ATOM 32 H10 UNK 0 1 -1.746 0.871 -0.520 1.00 0.00<br />
ATOM 33 H11 UNK 0 1 -2.722 1.857 -2.659 1.00 0.00<br />
ATOM 34 H12 UNK 0 1 5.584 6.194 3.134 1.00 0.00<br />
ATOM 35 H13 UNK 0 1 5.249 5.174 4.323 1.00 0.00<br />
ATOM 36 H14 UNK 0 1 6.345 6.509 4.442 1.00 0.00<br />
ATOM 37 H15 UNK 0 1 7.632 6.136 2.080 1.00 0.00<br />
ATOM 38 H16 UNK 0 1 9.036 5.224 2.674 1.00 0.00<br />
ATOM 39 H17 UNK 0 1 8.192 0.796 1.411 1.00 0.00<br />
ATOM 40 H18 UNK 0 1 6.845 1.683 0.891 1.00 0.00<br />
ATOM 41 H19 UNK 0 1 6.601 0.730 1.664 1.00 0.00<br />
ATOM 42 H20 UNK 0 1 3.287 5.000 -1.055 1.00 0.00<br />
ATOM 43 H21 UNK 0 1 3.641 5.431 -0.312 1.00 0.00<br />
ATOM 44 H22 UNK 0 1 4.744 4.677 -1.233 1.00 0.00<br />
ATOM 45 H23 UNK 0 1 -1.169 2.952 -3.075 1.00 0.00<br />
ATOM 46 H24 UNK 0 1 -1.270 3.988 -2.080 1.00 0.00<br />
ATOM 47 H25 UNK 0 1 -0.054 3.018 -3.313 1.00 0.00<br />
CONECT 1 6<br />
CONECT 2 17<br />
CONECT 3 4 8 19 20<br />
CONECT 4 3 5 23 24<br />
CONECT 5 4 6 25 26<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 18<br />
CONECT 8 3 7 9<br />
CONECT 9 8 10 27<br />
CONECT 10 9 11 28<br />
CONECT 11 10 12 21<br />
CONECT 12 11 13 29<br />
CONECT 13 12 14 30<br />
CONECT 14 13 15 31<br />
CONECT 15 14 16 22<br />
CONECT 16 15 17 32<br />
CONECT 17 2 16 33<br />
CONECT 18 7 39 40 41<br />
CONECT 19 3 34 35 36<br />
CONECT 20 3 37 38<br />
CONECT 21 11 42 43 44<br />
CONECT 22 15 45 46 47<br />
CONECT 23 4<br />
CONECT 24 4<br />
CONECT 25 5<br />
CONECT 26 5<br />
CONECT 27 9<br />
CONECT 28 10<br />
CONECT 29 12<br />
CONECT 30 13<br />
CONECT 31 14<br />
CONECT 32 16<br />
CONECT 33 17<br />
CONECT 34 19<br />
CONECT 35 19<br />
CONECT 36 19<br />
CONECT 37 20<br />
CONECT 38 20<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 18<br />
CONECT 42 21<br />
CONECT 43 21<br />
CONECT 44 21<br />
CONECT 45 22<br />
CONECT 46 22<br />
CONECT 47 22<br />
MASTER 0 0 0 0 0 0 0 0 47 0 47 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|[http://www.ch.ic.ac.uk/wiki/index.php/Image:Trans-retinal.cdx ChemDraw 3D structure]<br />
|}<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br>Compound A 3D Picture<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY CRETAL01<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 13.180 7.499 17.803 90.00 95.66 90.00 P 21/n 4<br />
ATOM 1 C1 UNK 0 1 3.279 5.402 15.975 1.00 0.00<br />
ATOM 2 C2 UNK 0 1 4.046 6.337 15.055 1.00 0.00<br />
ATOM 3 C3 UNK 0 1 3.501 7.731 15.036 1.00 0.00<br />
ATOM 4 C4 UNK 0 1 2.048 7.716 14.547 1.00 0.00<br />
ATOM 5 C5 UNK 0 1 1.242 6.570 15.071 1.00 0.00<br />
ATOM 6 C6 UNK 0 1 1.742 5.525 15.720 1.00 0.00<br />
ATOM 7 C7 UNK 0 1 0.960 4.412 16.249 1.00 0.00<br />
ATOM 8 C8 UNK 0 1 -0.096 3.785 15.688 1.00 0.00<br />
ATOM 9 C9 UNK 0 1 -0.891 2.748 16.260 1.00 0.00<br />
ATOM 10 C10 UNK 0 1 -2.039 2.359 15.656 1.00 0.00<br />
ATOM 11 C11 UNK 0 1 -2.995 1.432 16.171 1.00 0.00<br />
ATOM 12 C12 UNK 0 1 -4.118 0.952 15.603 1.00 0.00<br />
ATOM 13 C13 UNK 0 1 -4.579 1.155 14.210 1.00 0.00<br />
ATOM 14 C14 UNK 0 1 -3.772 1.162 13.168 1.00 0.00<br />
ATOM 15 C15 UNK 0 1 -4.144 1.290 11.748 1.00 0.00<br />
ATOM 16 O1 UNK 0 1 -3.417 1.200 10.832 1.00 0.00<br />
ATOM 17 C16 UNK 0 1 -0.251 6.757 14.825 1.00 0.00<br />
ATOM 18 C17 UNK 0 1 3.537 5.722 17.465 1.00 0.00<br />
ATOM 19 C18 UNK 0 1 3.755 3.989 15.704 1.00 0.00<br />
ATOM 20 C19 UNK 0 1 -0.446 2.130 17.555 1.00 0.00<br />
ATOM 21 C20 UNK 0 1 -6.097 1.275 14.125 1.00 0.00<br />
ATOM 22 H1 UNK 0 1 4.961 6.299 15.236 1.00 0.00<br />
ATOM 23 H2 UNK 0 1 4.033 6.074 13.960 1.00 0.00<br />
ATOM 24 H3 UNK 0 1 3.361 8.099 16.086 1.00 0.00<br />
ATOM 25 H4 UNK 0 1 4.112 8.346 14.368 1.00 0.00<br />
ATOM 26 H5 UNK 0 1 1.613 8.609 14.846 1.00 0.00<br />
ATOM 27 H6 UNK 0 1 2.096 8.271 13.429 1.00 0.00<br />
ATOM 28 H7 UNK 0 1 1.167 4.027 17.220 1.00 0.00<br />
ATOM 29 H8 UNK 0 1 -0.283 4.132 14.828 1.00 0.00<br />
ATOM 30 H9 UNK 0 1 -2.166 2.700 14.811 1.00 0.00<br />
ATOM 31 H10 UNK 0 1 -2.959 1.140 17.220 1.00 0.00<br />
ATOM 32 H11 UNK 0 1 -4.766 0.337 16.175 1.00 0.00<br />
ATOM 33 H12 UNK 0 1 -2.863 1.012 13.199 1.00 0.00<br />
ATOM 34 H13 UNK 0 1 -5.051 1.500 11.604 1.00 0.00<br />
ATOM 35 H14 UNK 0 1 -0.500 7.641 14.882 1.00 0.00<br />
ATOM 36 H15 UNK 0 1 -0.354 6.404 13.677 1.00 0.00<br />
ATOM 37 H16 UNK 0 1 -0.828 6.374 15.537 1.00 0.00<br />
ATOM 38 H17 UNK 0 1 4.443 5.482 17.539 1.00 0.00<br />
ATOM 39 H18 UNK 0 1 3.171 6.749 17.876 1.00 0.00<br />
ATOM 40 H19 UNK 0 1 2.971 5.092 18.159 1.00 0.00<br />
ATOM 41 H20 UNK 0 1 3.359 3.330 16.246 1.00 0.00<br />
ATOM 42 H21 UNK 0 1 3.564 3.712 14.704 1.00 0.00<br />
ATOM 43 H22 UNK 0 1 4.832 3.967 15.608 1.00 0.00<br />
ATOM 44 H23 UNK 0 1 0.526 2.025 17.433 1.00 0.00<br />
ATOM 45 H24 UNK 0 1 -0.489 2.700 18.230 1.00 0.00<br />
ATOM 46 H25 UNK 0 1 -1.006 1.387 18.000 1.00 0.00<br />
ATOM 47 H26 UNK 0 1 -6.646 0.300 14.793 1.00 0.00<br />
ATOM 48 H27 UNK 0 1 -6.440 2.100 14.580 1.00 0.00<br />
ATOM 49 H28 UNK 0 1 -6.271 1.320 13.269 1.00 0.00<br />
CONECT 1 2 6 18 19<br />
CONECT 2 1 3 22 23<br />
CONECT 3 2 4 24 25<br />
CONECT 4 3 5 26 27<br />
CONECT 5 4 6 17<br />
CONECT 6 1 5 7<br />
CONECT 7 6 8 28<br />
CONECT 8 7 9 29<br />
CONECT 9 8 10 20<br />
CONECT 10 9 11 30<br />
CONECT 11 10 12 31<br />
CONECT 12 11 13 32<br />
CONECT 13 12 14 21<br />
CONECT 14 13 15 33<br />
CONECT 15 14 16 34<br />
CONECT 16 15<br />
CONECT 17 5 35 36 37<br />
CONECT 18 1 38 39 40<br />
CONECT 19 1 41 42 43<br />
CONECT 20 9 44 45 46<br />
CONECT 21 13 47 48 49<br />
CONECT 22 2<br />
CONECT 23 2<br />
CONECT 24 3<br />
CONECT 25 3<br />
CONECT 26 4<br />
CONECT 27 4<br />
CONECT 28 7<br />
CONECT 29 8<br />
CONECT 30 10<br />
CONECT 31 11<br />
CONECT 32 12<br />
CONECT 33 14<br />
CONECT 34 15<br />
CONECT 35 17<br />
CONECT 36 17<br />
CONECT 37 17<br />
CONECT 38 18<br />
CONECT 39 18<br />
CONECT 40 18<br />
CONECT 41 19<br />
CONECT 42 19<br />
CONECT 43 19<br />
CONECT 44 20<br />
CONECT 45 20<br />
CONECT 46 20<br />
CONECT 47 21<br />
CONECT 48 21<br />
CONECT 49 21<br />
MASTER 0 0 0 0 0 0 0 0 49 0 49 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
Compound B 3D picture<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER CSD ENTRY TRETAL03<br />
COMPND UNNAMED<br />
AUTHOR GENERATED BY CONQUEST<br />
CRYST1 14.956 8.277 15.291 90.00 104.92 90.00 P 21/n 4<br />
ATOM 1 O1 UNK 0 1 9.309 3.852 9.139 1.00 0.00<br />
ATOM 2 C1 UNK 0 1 -1.723 -0.739 4.047 1.00 0.00<br />
ATOM 3 C2 UNK 0 1 -0.452 -1.316 3.444 1.00 0.00<br />
ATOM 4 C3 UNK 0 1 -2.519 -1.832 4.761 1.00 0.00<br />
ATOM 5 C4 UNK 0 1 -2.460 -0.197 2.791 1.00 0.00<br />
ATOM 6 C5 UNK 0 1 -3.484 0.764 3.073 1.00 0.00<br />
ATOM 7 C6 UNK 0 1 -3.039 1.904 3.908 1.00 0.00<br />
ATOM 8 C7 UNK 0 1 -2.002 1.579 4.954 1.00 0.00<br />
ATOM 9 C8 UNK 0 1 -1.767 2.692 5.929 1.00 0.00<br />
ATOM 10 C9 UNK 0 1 -1.402 0.397 5.000 1.00 0.00<br />
ATOM 11 C10 UNK 0 1 -0.360 0.092 6.017 1.00 0.00<br />
ATOM 12 C11 UNK 0 1 0.764 0.756 6.175 1.00 0.00<br />
ATOM 13 C12 UNK 0 1 1.826 0.493 7.151 1.00 0.00<br />
ATOM 14 C13 UNK 0 1 1.604 -0.603 8.138 1.00 0.00<br />
ATOM 15 C14 UNK 0 1 2.930 1.234 7.109 1.00 0.00<br />
ATOM 16 C15 UNK 0 1 4.081 1.142 7.980 1.00 0.00<br />
ATOM 17 C16 UNK 0 1 5.145 1.932 7.893 1.00 0.00<br />
ATOM 18 C17 UNK 0 1 6.289 1.962 8.796 1.00 0.00<br />
ATOM 19 C18 UNK 0 1 6.288 1.002 9.940 1.00 0.00<br />
ATOM 20 C19 UNK 0 1 7.263 2.851 8.564 1.00 0.00<br />
ATOM 21 C20 UNK 0 1 8.452 3.036 9.396 1.00 0.00<br />
CONECT 1 21<br />
CONECT 2 3 4 5 10<br />
CONECT 3 2<br />
CONECT 4 2<br />
CONECT 5 2 6<br />
CONECT 6 5 7<br />
CONECT 7 6 8<br />
CONECT 8 7 9 10<br />
CONECT 9 8<br />
CONECT 10 2 8 11<br />
CONECT 11 10 12<br />
CONECT 12 11 13<br />
CONECT 13 12 14 15<br />
CONECT 14 13<br />
CONECT 15 13 16<br />
CONECT 16 15 17<br />
CONECT 17 16 18<br />
CONECT 18 17 19 20<br />
CONECT 19 18<br />
CONECT 20 18 21<br />
CONECT 21 1 20<br />
MASTER 0 0 0 0 0 0 0 0 21 0 21 0<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
==Effects of Bunazosin on ocular circulation and retinal neuronal damage==<br />
<br />
By applying bunazosin hydrochloride into a healthy humans, it increases the blood velocity in the optic nerve head(ONH),retina and choroid, without changing either heart rate and blood pressure dramaticallt. This drug was also applied to rabbits and rats, giving positive results. These shows that bunazosin hydrochloride have improvement effect both in the ocular circulation and a direct neuroprotective effct. Therefore, it may be useful to use bunazosin hydrochloride as a therapeutic drug against retinal diseases which is associated with the ocular circulation.<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.<br />
*3.Hara, Hideaki / Ichikawa, Masaki / Oku, Hidehiro / Shimazawa, Masamitsu / Araie, Makoto, Cardiovascular drug reviews, Apr 2005</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=Talk:It:Gingerone&diff=4423
Talk:It:Gingerone
2006-10-27T07:45:43Z
<p>So105: /* So105's suggestion */ minor change + post</p>
<hr />
<div>=== So105's suggestion ===<br />
Suggestion for Bg105 on combining general and physical tables into one using the following code, what do you think? If you wish to use it clink on the Edit tab and copy the code.<br />
<br />
<br />
{| class="toccolours" border="1" style="fix: left; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''general properties''' <br />
|-<br />
| Chemical name<br />
| align="center" |4-(4-hydroxy-3-methoxyphenyl)-2-butanone<br />
|-<br />
| Chemical formula<br />
| align="center" |C<sub>11</sub>H<sub>14</sub>O<sub>3</sub><br />
|-<br />
| Molecular mass<br />
| align="center" |194 g/mol<br />
|-<br />
| SMILES<br />
| align="center" |OC1=C(OC)C=C(CCC(C)=O)C=C1<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''physical properties''' <br />
|-<br />
| Melting point<br />
| align="center" |40-42°C<br />
|-<br />
|}<br />
<br />
===Ss1305===<br />
I would like to know why the properties of gingerol are up when we are talking about zingerone. I put gingerol in a reaction as it is a way of producing zingerone.<br />
<br />
===So105===<br />
Please remember to add your user name if you post something, in order to avoid confusion, thankyou.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=4078
It:Retinal
2006-10-26T10:05:26Z
<p>So105: changed aka to also know...</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''', also known as retinaldehyde or retinene<sub>1</sub> is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="1" bgcolor="lt blue"|<br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Cis-Retinal''' <br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Trans-Retinal''' <br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''<br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''<br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)<br />
=C(C)CCC1<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)<br />
=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=4075
It:Retinal
2006-10-26T10:02:23Z
<p>So105: /* Properties of Cis-Retinal and Trans-Retinal */ fixed table</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="1" bgcolor="lt blue"|<br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Cis-Retinal''' <br />
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Trans-Retinal''' <br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''<br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''<br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)<br />
=C(C)CCC1<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)<br />
=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=4062
It:Sucralose
2006-10-26T09:32:25Z
<p>So105: /* Is Sucralose safe? */</p>
<hr />
<div>__toc__<br />
<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Safety of Sucralose use has been documented in more than 100 scientific studies over a 20-year period, which demonstrated that Sucralose is safe for Human consumption.<br />
<br />
*''"The data from the studies were independently evaluated by international experts in a variety of scientific disciplines, including toxicology, oncology, teratology, neurology, hematology, pediatrics and nutrition. Importantly, comprehensive toxicology studies, designed to meet the highest scientific standards, have clearly demonstrated that sucralose is not carcinogenic".'' IFIC Foundations<br />
<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=4060
It:Sucralose
2006-10-26T09:14:47Z
<p>So105: /* Properties of Sucralose */ minor change to table</p>
<hr />
<div>__toc__<br />
<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term and side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=4059
It:Sucralose
2006-10-26T09:13:00Z
<p>So105: Moved sucralose low calorie charac... to intro</p>
<hr />
<div>__toc__<br />
<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term and side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=4054
It:Sucralose
2006-10-26T09:07:54Z
<p>So105: /* Sucralose in detail */ changed tiltle and substitle</p>
<hr />
<div>==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Sucralose's low-calorie characteristic ===<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
=== Is Sucralose safe? ===<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term and side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3795
It:Sucralose
2006-10-24T12:53:17Z
<p>So105: /* Properties of Sucralose */</p>
<hr />
<div>==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose in detail==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Sucralose's low-calorie characteristic ===<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
=== Safety of Sucralose use? ===<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term and side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3787
It:Sucralose
2006-10-24T12:48:46Z
<p>So105: moved relavite po... to main table</p>
<hr />
<div>==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose in detail==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Sucralose's low-calorie characteristic ===<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
=== Safety of Sucralose use? ===<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term and side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3765
It:Sucralose
2006-10-24T12:30:51Z
<p>So105: added safety of sucralose + reordered subheadings</p>
<hr />
<div>==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
==Sucralose in detail==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Sucralose's low-calorie characteristic ===<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
=== Safety of Sucralose use? ===<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term and side effects of 1,6-dichlorofructose if any.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3672
It:Retinal
2006-10-24T11:05:13Z
<p>So105: /* Properties of Cis-Retinal and Trans-Retinal */</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Cis-Retinal''' <br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Trans-Retinal''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties'''<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous'''<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)<br />
=C(C)CCC1<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)<br />
=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3671
It:Retinal
2006-10-24T11:05:00Z
<p>So105: /* Properties of Cis-Retinal and Trans-Retinal */ added data</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Cis-Retinal''' <br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Trans-Retinal''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| Molecular mass<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties'''<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous'''<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)<br />
=C(C)CCC1<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)<br />
=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3661
It:Retinal
2006-10-24T10:48:31Z
<p>So105: /* Properties of Cis-Retinal and Trans-Retinal */</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Cis-Retinal''' <br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Trans-Retinal''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|Chemical formula<br />
| align="center"|...<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| Molecular mass<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties'''<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous'''<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)<br />
=C(C)CCC1<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)<br />
=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3660
It:Retinal
2006-10-24T10:48:15Z
<p>So105: /* Properties of Cis-Retinal and Trans-Retinal */</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Cis-Retinal''' <br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Trans-Retinal''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|Chemical formula<br />
| align="center"|...<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| Molecular mass<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties'''<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous'''<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\<br />
C=O)=C(C)CCC1<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/<br />
C=O)=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3658
It:Retinal
2006-10-24T10:47:37Z
<p>So105: /* Properties of Cis-Retinal and Trans-Retinal */ added smiles</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Cis-Retinal''' <br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Trans-Retinal''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|Chemical formula<br />
| align="center"|...<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| Molecular mass<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties'''<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous'''<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3655
It:Retinal
2006-10-24T10:43:58Z
<p>So105: /* Properties of Cis-Retinal */ added trans retinal to sub-title</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal and Trans-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Cis-Retinal''' <br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Trans-Retinal''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|Chemical formula<br />
| align="center"|...<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| Molecular mass<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties'''<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous'''<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
| SMILES<br />
| align="center"|...<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3653
It:Retinal
2006-10-24T10:43:16Z
<p>So105: /* Properties of all-trans retinal */ moved properties of trans-retinal</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Cis-Retinal''' <br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Trans-Retinal''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|Chemical formula<br />
| align="center"|...<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| Molecular mass<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties'''<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous'''<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
| SMILES<br />
| align="center"|...<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3652
It:Retinal
2006-10-24T10:42:51Z
<p>So105: /* Properties of Cis-Retinal */ added properties of Trans-retinal to table</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Cis-Retinal''' <br />
| align="center" colspan="2" bgcolor="lt blue"|'''General properties of Trans-Retinal''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|Chemical formula<br />
| align="center"|...<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
| Molecular mass<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties'''<br />
| align="center" colspan="2" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous'''<br />
| align="center" colspan="2" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
| SMILES<br />
| align="center"|...<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
==Properties of all-trans retinal==<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3644
It:Retinal
2006-10-24T10:33:47Z
<p>So105: /* Structure of Cis-Retinal */ changed size of 3d image</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
==Properties of all-trans retinal==<br />
<br />
==The role of retinal in the vision process==<br />
<br />
The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
==Synthesis of Rhodopsin==<br />
[[Image:Synthesis_of_rhodopsin.gif]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3641
It:Sucralose
2006-10-24T10:29:37Z
<p>So105: /* Structure of Sucralose */ changed size of 3D image</p>
<hr />
<div>==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="3" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
==History of Sucralose==<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener and was discovered in 1976 by Tate & Lyle sugar company.. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars, and found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
== Sucralose low-calorie characteristic ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3633
It:Sucralose
2006-10-24T10:22:36Z
<p>So105: /* Properties of Sucralose */minor changes</p>
<hr />
<div>==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="3" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
==History of Sucralose==<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener and was discovered in 1976 by Tate & Lyle sugar company.. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars, and found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
== Sucralose low-calorie characteristic ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3540
It:Sucralose
2006-10-23T15:33:28Z
<p>So105: /* Structure of Sucralose */</p>
<hr />
<div>==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="3" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-5-chloro-6-(hyd<br />
roxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
==History of Sucralose==<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener and was discovered in 1976 by Tate & Lyle sugar company.. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars, and found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
== Sucralose low-calorie characteristic ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3535
It:Sucralose
2006-10-23T15:30:03Z
<p>So105: back to normal</p>
<hr />
<div>==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>390</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="3" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-5-chloro-6-(hyd<br />
roxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
==History of Sucralose==<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener and was discovered in 1976 by Tate & Lyle sugar company.. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars, and found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
== Sucralose low-calorie characteristic ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3532
It:Sucralose
2006-10-23T15:27:46Z
<p>So105: </p>
<hr />
<div>== Sucralose in detail ==<br />
{| class="toccolours" border="0" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>390</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="3" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-5-chloro-6-(hyd<br />
roxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
==History of Sucralose==<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener and was discovered in 1976 by Tate & Lyle sugar company.. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars, and found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
== Sucralose low-calorie characteristic ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3501
It:Sucralose
2006-10-23T15:17:10Z
<p>So105: /* Structure of Sucralose */</p>
<hr />
<div>== Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="3" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-5-chloro-6-(hyd<br />
roxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
==History of Sucralose==<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, was discovered in 1976 by Tate & Lyle sugar company.. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars, and found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
== Sucralose in detail ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3496
It:Sucralose
2006-10-23T15:15:11Z
<p>So105: </p>
<hr />
<div>== Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="3" bgcolor="white"|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|1',4,6'-Trichloro-galactosucrose<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
==History of Sucralose==<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, was discovered in 1976 by Tate & Lyle sugar company.. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars, and found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
== Sucralose in detail ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3494
It:Sucralose
2006-10-23T15:14:25Z
<p>So105: /* Synthesis Of Sucralose From Sucrose */</p>
<hr />
<div>== Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="3" bgcolor="white"|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|1',4,6'-Trichloro-galactosucrose<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
==History of Sucralose==<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, was discovered in 1976 by Tate & Lyle sugar company.. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars, and found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
== Sucralose in detail ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3456
It:Sucralose
2006-10-23T15:01:25Z
<p>So105: /* History of sucralose */ small errors</p>
<hr />
<div>== Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
==History of Sucralose==<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, was discovered in 1976 by Tate & Lyle sugar company.. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars, and found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
== Sucralose in detail ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==The Synthesis Of Sucralose==<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms.<br />
The halogenation with chlorine increases the stability of the molecule.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3425
It:Sucralose
2006-10-23T14:53:22Z
<p>So105: /* Properties of Sucralose */</p>
<hr />
<div>== Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
== Sucralose in detail ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3423
It:Sucralose
2006-10-23T14:51:56Z
<p>So105: /* The relative potency of sugar compared with artificial sweeteners */change table style</p>
<hr />
<div>== Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder<br />
[[Image:Sci-of-sucralose.jpg]]<br />
(40 times their natural size)<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
== Sucralose in detail ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==The relative potency of sugar compared with artificial sweeteners==<br />
<br />
{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3400
It:Retinal
2006-10-23T14:43:06Z
<p>So105: Moved contents box to top</p>
<hr />
<div>__toc__<br />
<br />
'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.<br />
<br />
== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==Structure of all-trans retinal==<br />
'''2D Structure'''<br />
<br />
[[Image:AllTransRetinal.gif]]<br />
<br />
==Properties of all-trans retinal==<br />
<br />
==How is Retinal affected by the absorption of light?==<br />
<br />
The absorption of light causes the pi-bond to break allowing the molecule to rotate. This allows the retinal molecule to change shape. The new shape of the molecule affects the shape of the protein to which the retinal molecule is attached to. This process occurs via a signal that passes along the optic nerve.<br />
<br />
[[Image:RetinalConversion.png]]<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH<br />
<br />
*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0. <br />
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3352
It:Sucralose
2006-10-23T14:24:06Z
<p>So105: moved picture of sucralose into apperance box</p>
<hr />
<div>== Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
== Sucralose in detail ==<br />
Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3316
It:Sucralose
2006-10-23T14:08:31Z
<p>So105: /* Properties of Sucralose */ added appearance data</p>
<hr />
<div>Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
== Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
*</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3277
It:Retinal
2006-10-23T13:46:08Z
<p>So105: spacing change</p>
<hr />
<div>== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==How is Retinal affected by the absorption of light?==<br />
<br />
The absorption of light causes the pi-bond to break allowing the molecule to rotate. This allows the retinal molecule to change shape. The new shape of the molecule affects the shape of the protein to which the retinal molecule is attached to. This process occurs via a signal that passes along the optic nerve.<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3269
It:Retinal
2006-10-23T13:43:35Z
<p>So105: /* Properties of Cis-Retinal */ added new table rows</p>
<hr />
<div>== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==How is Retinal affected by the absorption of light?==<br />
<br />
The absorption of light causes the pi-bond to break allowing the molecule to rotate. This allows the retinal molecule to change shape. The new shape of the molecule affects the shape of the protein to which the retinal molecule is attached to. This process occurs via a signal that passes along the optic nerve.<br />
<br />
<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3248
It:Retinal
2006-10-23T13:34:22Z
<p>So105: /* References */ fixed reference</p>
<hr />
<div>== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''General properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
|-<br />
|}<br />
<br />
==How is Retinal affected by the absorption of light?==<br />
<br />
The absorption of light causes the pi-bond to break allowing the molecule to rotate. This allows the retinal molecule to change shape. The new shape of the molecule affects the shape of the protein to which the retinal molecule is attached to. This process occurs via a signal that passes along the optic nerve.<br />
<br />
<br />
<br />
== References ==<br />
<br />
*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3230
It:Retinal
2006-10-23T13:24:51Z
<p>So105: added reference</p>
<hr />
<div>== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''General properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
1. Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3225
It:Retinal
2006-10-23T13:17:13Z
<p>So105: /* Properties of Cis-Retinal */ added data to tables</p>
<hr />
<div>== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''General properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1<br />
|-<br />
|}</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3223
It:Retinal
2006-10-23T13:11:39Z
<p>So105: Added table of properties</p>
<hr />
<div>== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|(11Z)-retinal<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<sub>1</sub><br />
|-<br />
| Molecular mass<br />
| align="center"|284 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''General properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|...<br />
|-<br />
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous''' <br />
|-<br />
| SMILES<br />
| align="center"|...<br />
|-<br />
|}</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3221
It:Retinal
2006-10-23T13:00:58Z
<p>So105: added 3D structure</p>
<hr />
<div>== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" bgcolor="lt blue"|'''2D Structure'''<br />
| align="center" bgcolor="lt blue"|'''3D Structure'''<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
HEADER NONAME 23-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 23-Oct-06 0 NONE 4<br />
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0<br />
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0<br />
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0<br />
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0<br />
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0<br />
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0<br />
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0<br />
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0<br />
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0<br />
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0<br />
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0<br />
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0<br />
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0<br />
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0<br />
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0<br />
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0<br />
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0<br />
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0<br />
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0<br />
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0<br />
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0<br />
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0<br />
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0<br />
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0<br />
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0<br />
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0<br />
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0<br />
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0<br />
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0<br />
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0<br />
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0<br />
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0<br />
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0<br />
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0<br />
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0<br />
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0<br />
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0<br />
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0<br />
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0<br />
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0<br />
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0<br />
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0<br />
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0<br />
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0<br />
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0<br />
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0<br />
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0<br />
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0<br />
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 54<br />
CONECT 2 1 3 4 0 NONE 55<br />
CONECT 4 2 5 6 0 NONE 56<br />
CONECT 6 4 7 11 0 NONE 57<br />
CONECT 7 6 8 9 10 NONE 58<br />
CONECT 11 6 12 13 0 NONE 59<br />
CONECT 13 11 14 15 0 NONE 60<br />
CONECT 15 13 16 17 0 NONE 61<br />
CONECT 17 15 18 22 0 NONE 62<br />
CONECT 18 17 19 20 21 NONE 63<br />
CONECT 22 17 23 24 0 NONE 64<br />
CONECT 24 22 25 26 0 NONE 65<br />
CONECT 26 24 41 27 0 NONE 66<br />
CONECT 27 26 28 32 0 NONE 67<br />
CONECT 28 27 29 30 31 NONE 68<br />
CONECT 32 27 33 34 35 NONE 69<br />
CONECT 35 32 36 37 38 NONE 70<br />
CONECT 38 35 39 40 41 NONE 71<br />
CONECT 41 38 26 42 46 NONE 72<br />
CONECT 42 41 43 44 45 NONE 73<br />
CONECT 46 41 47 48 49 NONE 74<br />
END NONE 75<br />
NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Retinal&diff=3218
It:Retinal
2006-10-23T12:53:39Z
<p>So105: Added 2D structure</p>
<hr />
<div>== Structure of Cis-Retinal ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center"|2D Structure<br />
|-<br />
| [[image:Cis-RetinalSo.gif]]<br />
|-<br />
|}</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Cis-RetinalSo.gif&diff=3215
File:Cis-RetinalSo.gif
2006-10-23T12:47:25Z
<p>So105: </p>
<hr />
<div></div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:projects&diff=3213
It:projects
2006-10-23T12:42:58Z
<p>So105: /* Supplemental Project Page */ added new molecule (Retinal)</p>
<hr />
<div>__FORCETOC__<br />
<br />
'''''You MUST use the Edit buttons on the right to edit this content. Do NOT use the Edit button on the top of this page.'''''<br />
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This is an area where you can play without worrying what you do. Enter it by pressing the [Edit] button '''on the right''' and '''not''' at the top. Go here for a [http://en.wikipedia.org/wiki/Wikipedia:Cheatsheet ''cheat sheet''] summary of how to create a Wiki page. It's a free-for-all in here! Learn how to use a Wiki by coming here! PS This is how to do Greek: &Alpha;, &alpha;, &beta; &Delta;, &delta; <br />
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== Main Project Page ==<br />
'''Please do not edit this page itself'''. Click on one of the titles to start editing.<br />
{| summary="CIT Project Titles" border="1"<br />
! bgcolor="cyan" |Project<br /> Number<br />
! bgcolor="cyan" |General Keywords<br />
|-<br />
| bgcolor="#CCFF00" |01<br />
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]<br />
|-<br />
| bgcolor="#CCFF00" |02<br />
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]<br />
|-<br />
| bgcolor="#CCFF00" |03<br />
| bgcolor="#CCFF00" | [[it:Rapamycin|Rapamycin (prevents transplant rejection)]]<br />
|-<br />
| bgcolor="#CCFF00" |04<br />
| bgcolor="#66FF99" | [[it:Gossypol|Gossypol (male birth control)]]<br />
|-<br />
| bgcolor="#CCFF00" |05<br />
| bgcolor="#CCFF00" | [[it:Gentamycin|Gentamicin A (aminoglycoside antibiotic)]]<br />
|-<br />
| bgcolor="#CCFF00" |06<br />
| bgcolor="#66FF99" | [[it:Herceptin|Herceptin (topical anticancer drug)]]<br />
|-<br />
| bgcolor="#CCFF00" |07<br />
| bgcolor="#CCFF00" | [[it:Gingerone|Zingerone (the characteristic smell of ginger)]]<br />
|-<br />
| bgcolor="#CCFF00" |08<br />
| bgcolor="#66FF99" | [[it:Sucralose|Sucralose (non-metabolizable sweetening agent)]]<br />
|-<br />
| bgcolor="#CCFF00" |09<br />
| bgcolor="#CCFF00" | [[it:Bufotoxin|Bufotoxin (active component of the toad ''Bufo vulgaris'')]]<br />
|-<br />
| bgcolor="#CCFF00" |10<br />
| bgcolor="#66FF99" | [[it:Roaccutane|Roaccutane (treatment for severe acne)]]<br />
|-<br />
| bgcolor="#CCFF00" |11<br />
| bgcolor="#CCFF00" | [[it:Sibutramine|Sibutramine (appetite suppresor)]]<br />
|-<br />
| bgcolor="#CCFF00" |12<br />
| bgcolor="#66FF99" | [[it:Anandamide|Anandamide (the "feel-good" factor in chocolate)]]<br />
|-<br />
| bgcolor="#CCFF00" |13<br />
| bgcolor="#CCFF00" | [[it:h3nbh3|Ammonia-borane: H<sub>3</sub>N-BH<sub>3</sub> (Hydrogen storage molecule?)]]<br />
|-<br />
| bgcolor="#CCFF00" |14<br />
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]<br />
|-<br />
| bgcolor="#CCFF00" |15<br />
| bgcolor="#CCFF00" | [[it:Hycocine|Hyoscine (From Mandrake and Witches Henbane, pre-med before surgery)]]<br />
|-<br />
| bgcolor="#CCFF00" |16<br />
| bgcolor="#66FF99" | [[it:Capreomycin|Capreomycin (Drug-resistant TB)]]<br />
|-<br />
| bgcolor="#CCFF00" |17<br />
| bgcolor="#CCFF00" | [[it:wilkinson|Wilkinson's catalyst]]<br />
|-<br />
| bgcolor="#CCFF00" |18<br />
| bgcolor="#66FF99" | [[it:Jacobsen|Jacobsen's epoxidation catalyst]]<br />
|-<br />
| bgcolor="#CCFF00" |19<br />
| bgcolor="#CCFF00" | [[it:Methylaluminoxane|Methylaluminoxane: MAO - hugely important ethylene polymerisation cocatalyst]]<br />
|-<br />
| bgcolor="#CCFF00" |20<br />
| bgcolor="#66FF99" | [[it:Schwartz|Schwartz reagent for the hydrozirconation of alkenes and alkynes]]<br />
|}<br />
<br />
== Supplemental Project Page ==<br />
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This area is for people who wish to create their own projects if none of the above appeal to them. Click on the '''Edit''' button to the right to open up an editable page,<br />
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*<nowiki> [[it:name_of_project|Descriptive name of intended project]]</nowiki><br />
*This will produce the effect: [[it:name_of_project|Descriptive name of intended project]]<br />
----<br />
*[[it:sitagliptin_page|Sitagliptin]]<br />
*[[it:Retinal|Retinal, molecule of slight]]<br />
<br />
== [[Special:Export|Export Pages]] ==<br />
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This takes you to an '''Export''' page. A backup of the Projects area can be made (in XML) if you want to keep your own<br />
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== Overlaps ==<br />
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If two people start editing a page at the same time, and '''save''' the change simultaneously, its possible only one of the changes<br />
will be made permanent. If anyone spots this happening, please let me know. <br />
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One precaution you could take is to keep a copy of the contents of the page you are editing in eg Wordpad (or Word),<br />
make the changes there, and then copy the entire lot to the Wiki page to preview and then save. Tht way, if your contribution<br />
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----<br />
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<br />
----<br />
[[Template:Chem-Data]]</div>
So105
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=3211
It:Sucralose
2006-10-23T12:35:04Z
<p>So105: minor change to main text</p>
<hr />
<div>Sucralose is sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to surgar but is around 600 times sweeter. Sucralose low-calorie characteristic originates from its inability for most of the substance to be metabolised by the body, although this molecule is made from sugar the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
== Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|...<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|... °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Apparence<br />
| align="center"|...<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
1. [http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose</div>
So105