ChemWiki - User contributions [en]

It:Jacobsen

2006-10-26T15:10:55Z

Pdm05: /* Asymmetric Epoxidation of Alkenes */

=='''Jacobsen Catalyst'''==
==='''Introduction'''===
Jacobsen catalyst is the most efficient and commercially available compound among the chiral manganese(III)-salen complexes with the IUPAC name: ''N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexylmanganese(III) chloride''. As the name suggests, the compound is widely used as a catalyst in the epoxidation of olefins for its enantioseletivity.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Jacobsen Catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Jacobsen_catalyst.gif]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexylmanganese(III) chloride''
|-
| [[CAS nummber]]
| 138124-32-0
|-
| [[Chemical formula]]
| {{{formula|C36H52ClMnN2O2
|-
| [[Molecular mass]]
| {{{mol_mass|635.21 g/mol
|-
| [[Simplified molecular input line entry specification|SMILES]]
| {{{SMILES|[Me3C]C(C=C2C(C)(C)C)=CC1=C2O[Mn+3]45[N]([C@H]3[C@H]
([N]4=CC(C=C(C(C)(C)C)C=C6[Me3C])=C6O5)CCCC3)=C1
|-
| [[Colour]]
| {{{Colour| Brown
|-
|}

<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; cpk off;frame 3; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 C 0 -5.987 -2.724 0.763 0.00 0.00 C+0
ATOM 2 C 0 -5.157 -2.243 -0.430 0.00 0.00 C+0
ATOM 3 C 0 -3.953 -1.487 0.069 0.00 0.00 C+0
ATOM 4 C 0 -3.029 -2.117 0.886 0.00 0.00 C+0
ATOM 5 C 0 -1.915 -1.431 1.316 0.00 0.00 C+0
ATOM 6 C 0 -0.915 -2.125 2.205 0.00 0.00 C+0
ATOM 7 C 0 -1.395 -3.547 2.500 0.00 0.00 C+0
ATOM 8 C 0 0.442 -2.181 1.499 0.00 0.00 C+0
ATOM 9 C 0 -0.776 -1.350 3.517 0.00 0.00 C+0
ATOM 10 C 0 -3.768 -0.176 -0.292 0.00 0.00 C+0
ATOM 11 C 0 -2.649 0.553 0.160 0.00 0.00 C+0
ATOM 12 C 0 -1.697 -0.105 0.941 0.00 0.00 C+0
ATOM 13 O 0 -0.457 0.388 1.349 0.00 0.00 O+0
ATOM 14 Mn 0 -0.037 1.374 -0.073 0.00 0.00 Mn+3
ATOM 15 N 0 -1.515 2.546 -0.267 0.00 0.00 N+0
ATOM 16 C 0 -0.898 3.821 -0.006 0.00 0.00 C+0
ATOM 17 H 0 -1.110 4.047 1.039 0.00 0.00 H+0
ATOM 18 C 0 0.645 3.896 -0.139 0.00 0.00 C+0
ATOM 19 H 0 0.866 4.224 -1.154 0.00 0.00 H+0
ATOM 20 N 0 1.363 2.659 0.121 0.00 0.00 N+0
ATOM 21 C 0 2.516 2.124 0.253 0.00 0.00 C+0
ATOM 22 C 0 2.606 0.693 -0.168 0.00 0.00 C+0
ATOM 23 C 0 3.768 0.042 0.299 0.00 0.00 C+0
ATOM 24 C 0 4.040 -1.260 -0.032 0.00 0.00 C+0
ATOM 25 C 0 5.286 -1.927 0.491 0.00 0.00 C+0
ATOM 26 C 0 6.066 -0.938 1.360 0.00 0.00 C+0
ATOM 27 C 0 4.898 -3.147 1.329 0.00 0.00 C+0
ATOM 28 C 0 6.159 -2.372 -0.684 0.00 0.00 C+0
ATOM 29 C 0 3.169 -1.964 -0.848 0.00 0.00 C+0
ATOM 30 C 0 2.020 -1.356 -1.300 0.00 0.00 C+0
ATOM 31 C 0 1.077 -2.126 -2.189 0.00 0.00 C+0
ATOM 32 C 0 1.620 -3.540 -2.405 0.00 0.00 C+0
ATOM 33 C 0 -0.300 -2.204 -1.527 0.00 0.00 C+0
ATOM 34 C 0 0.955 -1.415 -3.539 0.00 0.00 C+0
ATOM 35 C 0 1.711 -0.042 -0.950 0.00 0.00 C+0
ATOM 36 O 0 0.480 0.395 -1.461 0.00 0.00 O+0
ATOM 37 C 0 1.058 5.040 0.808 0.00 0.00 C+0
ATOM 38 C 0 0.492 6.328 0.192 0.00 0.00 C+0
ATOM 39 C 0 -1.021 6.266 0.017 0.00 0.00 C+0
ATOM 40 C 0 -1.434 5.015 -0.798 0.00 0.00 C+0
ATOM 41 C 0 -2.677 2.003 -0.219 0.00 0.00 C+0
ATOM 42 C 0 -4.698 -3.449 -1.252 0.00 0.00 C+0
ATOM 43 C 0 -6.010 -1.323 -1.306 0.00 0.00 C+0
ATOM 44 H 0 -6.313 -1.865 1.348 0.00 0.00 H+0
ATOM 45 H 0 -6.858 -3.271 0.402 0.00 0.00 H+0
ATOM 46 H 0 -5.379 -3.379 1.387 0.00 0.00 H+0
ATOM 47 H 0 -3.182 -3.143 1.186 0.00 0.00 H+0
ATOM 48 H 0 -1.494 -4.099 1.565 0.00 0.00 H+0
ATOM 49 H 0 -0.672 -4.049 3.143 0.00 0.00 H+0
ATOM 50 H 0 -2.361 -3.507 3.003 0.00 0.00 H+0
ATOM 51 H 0 0.709 -1.185 1.146 0.00 0.00 H+0
ATOM 52 H 0 1.200 -2.534 2.198 0.00 0.00 H+0
ATOM 53 H 0 0.382 -2.863 0.651 0.00 0.00 H+0
ATOM 54 H 0 -1.742 -1.311 4.019 0.00 0.00 H+0
ATOM 55 H 0 -0.052 -1.852 4.160 0.00 0.00 H+0
ATOM 56 H 0 -0.433 -0.337 3.306 0.00 0.00 H+0
ATOM 57 H 0 -4.491 0.306 -0.932 0.00 0.00 H+0
ATOM 58 H 0 3.365 2.667 0.640 0.00 0.00 H+0
ATOM 59 H 0 4.458 0.582 0.931 0.00 0.00 H+0
ATOM 60 H 0 5.445 -0.621 2.198 0.00 0.00 H+0
ATOM 61 H 0 6.968 -1.420 1.739 0.00 0.00 H+0
ATOM 62 H 0 6.343 -0.069 0.764 0.00 0.00 H+0
ATOM 63 H 0 4.343 -3.851 0.710 0.00 0.00 H+0
ATOM 64 H 0 5.800 -3.629 1.708 0.00 0.00 H+0
ATOM 65 H 0 4.277 -2.830 2.167 0.00 0.00 H+0
ATOM 66 H 0 6.435 -1.502 -1.281 0.00 0.00 H+0
ATOM 67 H 0 7.060 -2.854 -0.305 0.00 0.00 H+0
ATOM 68 H 0 5.603 -3.076 -1.303 0.00 0.00 H+0
ATOM 69 H 0 3.390 -2.983 -1.128 0.00 0.00 H+0
ATOM 70 H 0 1.708 -4.046 -1.444 0.00 0.00 H+0
ATOM 71 H 0 0.938 -4.096 -3.049 0.00 0.00 H+0
ATOM 72 H 0 2.601 -3.484 -2.877 0.00 0.00 H+0
ATOM 73 H 0 -0.558 -1.230 -1.111 0.00 0.00 H+0
ATOM 74 H 0 -1.044 -2.491 -2.269 0.00 0.00 H+0
ATOM 75 H 0 -0.277 -2.946 -0.729 0.00 0.00 H+0
ATOM 76 H 0 1.936 -1.359 -4.011 0.00 0.00 H+0
ATOM 77 H 0 0.273 -1.971 -4.182 0.00 0.00 H+0
ATOM 78 H 0 0.568 -0.407 -3.385 0.00 0.00 H+0
ATOM 79 H 0 0.632 4.879 1.799 0.00 0.00 H+0
ATOM 80 H 0 2.145 5.100 0.871 0.00 0.00 H+0
ATOM 81 H 0 0.739 7.169 0.840 0.00 0.00 H+0
ATOM 82 H 0 0.954 6.487 -0.782 0.00 0.00 H+0
ATOM 83 H 0 -1.492 6.240 1.000 0.00 0.00 H+0
ATOM 84 H 0 -1.355 7.159 -0.512 0.00 0.00 H+0
ATOM 85 H 0 -1.003 5.059 -1.798 0.00 0.00 H+0
ATOM 86 H 0 -2.521 4.948 -0.858 0.00 0.00 H+0
ATOM 87 H 0 -3.589 2.540 -0.431 0.00 0.00 H+0
ATOM 88 H 0 -5.570 -3.995 -1.612 0.00 0.00 H+0
ATOM 89 H 0 -4.107 -3.106 -2.101 0.00 0.00 H+0
ATOM 90 H 0 -4.091 -4.104 -0.628 0.00 0.00 H+0
ATOM 91 H 0 -6.337 -0.464 -0.720 0.00 0.00 H+0
ATOM 92 H 0 -5.419 -0.980 -2.155 0.00 0.00 H+0
ATOM 93 H 0 -6.881 -1.869 -1.666 0.00 0.00 H+0
CONECT 1 2 44 45 46 NONE 98
CONECT 2 1 3 42 43 NONE 99
CONECT 3 2 4 10 0 NONE 100
CONECT 4 3 5 47 0 NONE 101
CONECT 5 4 12 6 0 NONE 102
CONECT 6 5 7 8 9 NONE 103
CONECT 7 6 48 49 50 NONE 104
CONECT 8 6 51 52 53 NONE 105
CONECT 9 6 54 55 56 NONE 106
CONECT 10 3 11 57 0 NONE 107
CONECT 11 10 41 12 0 NONE 108
CONECT 12 11 5 13 0 NONE 109
CONECT 13 12 14 0 0 NONE 110
CONECT 14 13 20 36 15 NONE 111
CONECT 15 14 16 41 0 NONE 112
CONECT 16 15 17 40 18 NONE 113
CONECT 18 16 19 20 37 NONE 114
CONECT 20 18 14 21 0 NONE 115
CONECT 21 20 22 58 0 NONE 116
CONECT 22 21 23 35 0 NONE 117
CONECT 23 22 24 59 0 NONE 118
CONECT 24 23 25 29 0 NONE 119
CONECT 25 24 26 27 28 NONE 120
CONECT 26 25 60 61 62 NONE 121
CONECT 27 25 63 64 65 NONE 122
CONECT 28 25 66 67 68 NONE 123
CONECT 29 24 30 69 0 NONE 124
CONECT 30 29 35 31 0 NONE 125
CONECT 31 30 32 33 34 NONE 126
CONECT 32 31 70 71 72 NONE 127
CONECT 33 31 73 74 75 NONE 128
CONECT 34 31 76 77 78 NONE 129
CONECT 35 22 30 36 0 NONE 130
CONECT 36 35 14 0 0 NONE 131
CONECT 37 18 38 79 80 NONE 132
CONECT 38 37 39 81 82 NONE 133
CONECT 39 38 40 83 84 NONE 134
CONECT 40 39 16 85 86 NONE 135
CONECT 41 15 11 87 0 NONE 136
CONECT 42 2 88 89 90 NONE 137
CONECT 43 2 91 92 93 NONE 138
END NONE 139
</inlineContents>
</jmolApplet>
</jmol>

The compound was developed by Professor Jacobsen of Harvard University from around 1990s.

----

==='''Preparation of the catalyst'''===
[[Image: Jacobsen catalyst preparation.gif ]]
----

== Asymmetric Epoxidation of Alkenes ==

[[Image:Jacobsen catalyst epoxidation of alekenes.gif|thumb|Description]]

In the conversion of an alkene to an epoxide, iodosylmesitylene can be used as an oxygen source. The oxygen atom is released onto the manganese(III) ion, with which the oxygen binds forming manganese(V). The oxygen atom can then be delivered to the alkene to form the epoxide.

[[Image:Jacobsen side-on epoxidation.gif|thumb|right|]]

The delivery method of alkene to oxygen is proposed to occur in a side-on approach, and is consistent with reactivity and enantioselectivity data mainly carried out by J.T. Groves - J. Am. Chem. Soc. 1983, 107, 5791-5796.

The alkene will insert itself next to the manganese centre of the catalyst in such a way to reduce steric interactions. This is done through a side-on approach, perpendicaular to the manganese-oxygen bond, with the alkene passing over the chiral carbon and nitrogen atoms. This is the least hindered method of approach. Approach from the other side of the catalyst is disfavoured by the dissymmetry of the catalyst. The diagram on the right shows the method of approach over the region where the chiral carbons are located, marked *, the nitrogen atoms, marked X, and the manganese marked M.

==='''References'''===
1. Cepanec, I. I. (2001). "An improved method for synthesis of Jacobsen's catalyst." Synthetic communications 31(19): 2913.

2. Flessner, T. T. (1999). "N,N'-bis(3,5-di-t-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride. The Jacobsen catalyst." 341(5): 436.

3. Jacobsen, E. N. E. (1991). "Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane." Journal of the American Chemical Society 113(18): 7063.

4. J. Am. Chem. Soc. 1990, 112, 2801-2803 - asymmetric epoxidation of alkenes.

5. Acc. Chem. Res. 2000, 33, 421-431.

----
==='''Background'''===
Jacobsen's catalyst(1) is made in 1994 by professor Jacobsen, use in converts achiral olefins to chiral epoxides with enantiomeric excesses regularly better than 90% sometime even higher. To date, the selectivity of this reaction has be understood.

[[image:Transformation1.gif]]
(Figure 1)

Jacobsen's Catalyst is a epoxidation catalysts based on a chiral salen ligand complexed with Manganese(III) (the base salen ligand is drawn in red).

[[image:Jacobsen's_Catalyst(1).gif]]

(Figure 2),Jacobsen's Catalyst (1) and the first salen catalyst introduced by Jacobsen (2)

Jacobsen's catalyst is the most convenient and effective compound for stereoselective synthesis in producing the side chain in the antitumour drug Taxol. Jacobsen has reported a simple large-scale preparation of catalyst,making it readily in large quantity. The reaction requires only a small amount of catalylst to substrate while making use of common bleach which is a low cost oxidant.

There are two related but distinct aspects for the reaction, the oxygen transfer and the chiral induction. However neither aspect can be explained fully.

[[image:Cycle1.gif]]

(Figure 3),The epoxidation occurs by a two step catalytic cycle

The oxygen transfer is known to occur by a two step catalytic cycle (Figure 3), similar to the accepted mechanism of metal porphyrin catalysed epoxidations. An oxidant transfers atomic oxygen to the Mn(III) catalyst in the first step. The oxygen presumably coordinates to the metal in a site normal to the porphyrin or salen plane, and the activated oxygen is then delivered to the alkene. This cycle, as opposed to assisted transfer by a complex aggregate, is supported by observations that several oxidants have been used with identical selectivity, that the reaction consumes stoichiometric quantities of an oxidant in the process of converting an alkene to an epoxide, and that related salen complexes show incorporation of oxygen from in situ labelled water, which does not occur via exchange with the oxidant or epoxide.

Oxygen transfer from the catalyst to the olefin has been hypothesized to occur by several different mechanisms (Figure 4) including attack of an oxygen radical intermediate on the double bond (A), concerted oxygen delivery (B), and formation of a metallaoxetane intermediate (C).

[[image:Modesoxtransfer1.gif]]

(Figure 4),Three possible ways of oxygen delivery

Even thought a mechanism which a metallaoxetane is a plausible intermediate is given by Norrby and coworkers, Jacobsen has demonstrated that it is likely oxidation of different olefins occurs by different mechanisms,it is generally accepted that oxygen transfer to olefins with radical stabilizing groups occurs by an attack of an oxygen centred radical on the olefin. This mode of oxygen delivery is supported by the observation that cis olefins result in both cis and trans epoxides.

The second aspect of the epoxidation mechanism must occur in the second step of the catalytic cycle where oxygen is transferred from the oxo-manganese complex to the epoxide. Fundamental to this stereoselection is the relative orientation of the activated catalyst and the olefin in the first irreversible bond formation.

File:Jacobsen side-on epoxidation.gif

2006-10-26T14:55:45Z

Pdm05:

It:Jacobsen

2006-10-26T14:55:10Z

Pdm05: /* Asymmetric Epoxidation of Alkenes */

=='''Jacobsen Catalyst'''==
==='''Introduction'''===
Jacobsen catalyst is the most efficient and commercially available compound among the chiral manganese(III)-salen complexes with the IUPAC name: ''N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexylmanganese(III) chloride''. As the name suggests, the compound is widely used as a catalyst in the epoxidation of olefins for its enantioseletivity.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Jacobsen Catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Jacobsen_catalyst.gif]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexylmanganese(III) chloride''
|-
| [[CAS nummber]]
| 138124-32-0
|-
| [[Chemical formula]]
| {{{formula|C36H52ClMnN2O2
|-
| [[Molecular mass]]
| {{{mol_mass|635.21 g/mol
|-
| [[Simplified molecular input line entry specification|SMILES]]
| {{{SMILES|[Me3C]C(C=C2C(C)(C)C)=CC1=C2O[Mn+3]45[N]([C@H]3[C@H]
([N]4=CC(C=C(C(C)(C)C)C=C6[Me3C])=C6O5)CCCC3)=C1
|-
| [[Colour]]
| {{{Colour| Brown
|-
|}

<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; cpk off;frame 3; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 C 0 -5.987 -2.724 0.763 0.00 0.00 C+0
ATOM 2 C 0 -5.157 -2.243 -0.430 0.00 0.00 C+0
ATOM 3 C 0 -3.953 -1.487 0.069 0.00 0.00 C+0
ATOM 4 C 0 -3.029 -2.117 0.886 0.00 0.00 C+0
ATOM 5 C 0 -1.915 -1.431 1.316 0.00 0.00 C+0
ATOM 6 C 0 -0.915 -2.125 2.205 0.00 0.00 C+0
ATOM 7 C 0 -1.395 -3.547 2.500 0.00 0.00 C+0
ATOM 8 C 0 0.442 -2.181 1.499 0.00 0.00 C+0
ATOM 9 C 0 -0.776 -1.350 3.517 0.00 0.00 C+0
ATOM 10 C 0 -3.768 -0.176 -0.292 0.00 0.00 C+0
ATOM 11 C 0 -2.649 0.553 0.160 0.00 0.00 C+0
ATOM 12 C 0 -1.697 -0.105 0.941 0.00 0.00 C+0
ATOM 13 O 0 -0.457 0.388 1.349 0.00 0.00 O+0
ATOM 14 Mn 0 -0.037 1.374 -0.073 0.00 0.00 Mn+3
ATOM 15 N 0 -1.515 2.546 -0.267 0.00 0.00 N+0
ATOM 16 C 0 -0.898 3.821 -0.006 0.00 0.00 C+0
ATOM 17 H 0 -1.110 4.047 1.039 0.00 0.00 H+0
ATOM 18 C 0 0.645 3.896 -0.139 0.00 0.00 C+0
ATOM 19 H 0 0.866 4.224 -1.154 0.00 0.00 H+0
ATOM 20 N 0 1.363 2.659 0.121 0.00 0.00 N+0
ATOM 21 C 0 2.516 2.124 0.253 0.00 0.00 C+0
ATOM 22 C 0 2.606 0.693 -0.168 0.00 0.00 C+0
ATOM 23 C 0 3.768 0.042 0.299 0.00 0.00 C+0
ATOM 24 C 0 4.040 -1.260 -0.032 0.00 0.00 C+0
ATOM 25 C 0 5.286 -1.927 0.491 0.00 0.00 C+0
ATOM 26 C 0 6.066 -0.938 1.360 0.00 0.00 C+0
ATOM 27 C 0 4.898 -3.147 1.329 0.00 0.00 C+0
ATOM 28 C 0 6.159 -2.372 -0.684 0.00 0.00 C+0
ATOM 29 C 0 3.169 -1.964 -0.848 0.00 0.00 C+0
ATOM 30 C 0 2.020 -1.356 -1.300 0.00 0.00 C+0
ATOM 31 C 0 1.077 -2.126 -2.189 0.00 0.00 C+0
ATOM 32 C 0 1.620 -3.540 -2.405 0.00 0.00 C+0
ATOM 33 C 0 -0.300 -2.204 -1.527 0.00 0.00 C+0
ATOM 34 C 0 0.955 -1.415 -3.539 0.00 0.00 C+0
ATOM 35 C 0 1.711 -0.042 -0.950 0.00 0.00 C+0
ATOM 36 O 0 0.480 0.395 -1.461 0.00 0.00 O+0
ATOM 37 C 0 1.058 5.040 0.808 0.00 0.00 C+0
ATOM 38 C 0 0.492 6.328 0.192 0.00 0.00 C+0
ATOM 39 C 0 -1.021 6.266 0.017 0.00 0.00 C+0
ATOM 40 C 0 -1.434 5.015 -0.798 0.00 0.00 C+0
ATOM 41 C 0 -2.677 2.003 -0.219 0.00 0.00 C+0
ATOM 42 C 0 -4.698 -3.449 -1.252 0.00 0.00 C+0
ATOM 43 C 0 -6.010 -1.323 -1.306 0.00 0.00 C+0
ATOM 44 H 0 -6.313 -1.865 1.348 0.00 0.00 H+0
ATOM 45 H 0 -6.858 -3.271 0.402 0.00 0.00 H+0
ATOM 46 H 0 -5.379 -3.379 1.387 0.00 0.00 H+0
ATOM 47 H 0 -3.182 -3.143 1.186 0.00 0.00 H+0
ATOM 48 H 0 -1.494 -4.099 1.565 0.00 0.00 H+0
ATOM 49 H 0 -0.672 -4.049 3.143 0.00 0.00 H+0
ATOM 50 H 0 -2.361 -3.507 3.003 0.00 0.00 H+0
ATOM 51 H 0 0.709 -1.185 1.146 0.00 0.00 H+0
ATOM 52 H 0 1.200 -2.534 2.198 0.00 0.00 H+0
ATOM 53 H 0 0.382 -2.863 0.651 0.00 0.00 H+0
ATOM 54 H 0 -1.742 -1.311 4.019 0.00 0.00 H+0
ATOM 55 H 0 -0.052 -1.852 4.160 0.00 0.00 H+0
ATOM 56 H 0 -0.433 -0.337 3.306 0.00 0.00 H+0
ATOM 57 H 0 -4.491 0.306 -0.932 0.00 0.00 H+0
ATOM 58 H 0 3.365 2.667 0.640 0.00 0.00 H+0
ATOM 59 H 0 4.458 0.582 0.931 0.00 0.00 H+0
ATOM 60 H 0 5.445 -0.621 2.198 0.00 0.00 H+0
ATOM 61 H 0 6.968 -1.420 1.739 0.00 0.00 H+0
ATOM 62 H 0 6.343 -0.069 0.764 0.00 0.00 H+0
ATOM 63 H 0 4.343 -3.851 0.710 0.00 0.00 H+0
ATOM 64 H 0 5.800 -3.629 1.708 0.00 0.00 H+0
ATOM 65 H 0 4.277 -2.830 2.167 0.00 0.00 H+0
ATOM 66 H 0 6.435 -1.502 -1.281 0.00 0.00 H+0
ATOM 67 H 0 7.060 -2.854 -0.305 0.00 0.00 H+0
ATOM 68 H 0 5.603 -3.076 -1.303 0.00 0.00 H+0
ATOM 69 H 0 3.390 -2.983 -1.128 0.00 0.00 H+0
ATOM 70 H 0 1.708 -4.046 -1.444 0.00 0.00 H+0
ATOM 71 H 0 0.938 -4.096 -3.049 0.00 0.00 H+0
ATOM 72 H 0 2.601 -3.484 -2.877 0.00 0.00 H+0
ATOM 73 H 0 -0.558 -1.230 -1.111 0.00 0.00 H+0
ATOM 74 H 0 -1.044 -2.491 -2.269 0.00 0.00 H+0
ATOM 75 H 0 -0.277 -2.946 -0.729 0.00 0.00 H+0
ATOM 76 H 0 1.936 -1.359 -4.011 0.00 0.00 H+0
ATOM 77 H 0 0.273 -1.971 -4.182 0.00 0.00 H+0
ATOM 78 H 0 0.568 -0.407 -3.385 0.00 0.00 H+0
ATOM 79 H 0 0.632 4.879 1.799 0.00 0.00 H+0
ATOM 80 H 0 2.145 5.100 0.871 0.00 0.00 H+0
ATOM 81 H 0 0.739 7.169 0.840 0.00 0.00 H+0
ATOM 82 H 0 0.954 6.487 -0.782 0.00 0.00 H+0
ATOM 83 H 0 -1.492 6.240 1.000 0.00 0.00 H+0
ATOM 84 H 0 -1.355 7.159 -0.512 0.00 0.00 H+0
ATOM 85 H 0 -1.003 5.059 -1.798 0.00 0.00 H+0
ATOM 86 H 0 -2.521 4.948 -0.858 0.00 0.00 H+0
ATOM 87 H 0 -3.589 2.540 -0.431 0.00 0.00 H+0
ATOM 88 H 0 -5.570 -3.995 -1.612 0.00 0.00 H+0
ATOM 89 H 0 -4.107 -3.106 -2.101 0.00 0.00 H+0
ATOM 90 H 0 -4.091 -4.104 -0.628 0.00 0.00 H+0
ATOM 91 H 0 -6.337 -0.464 -0.720 0.00 0.00 H+0
ATOM 92 H 0 -5.419 -0.980 -2.155 0.00 0.00 H+0
ATOM 93 H 0 -6.881 -1.869 -1.666 0.00 0.00 H+0
CONECT 1 2 44 45 46 NONE 98
CONECT 2 1 3 42 43 NONE 99
CONECT 3 2 4 10 0 NONE 100
CONECT 4 3 5 47 0 NONE 101
CONECT 5 4 12 6 0 NONE 102
CONECT 6 5 7 8 9 NONE 103
CONECT 7 6 48 49 50 NONE 104
CONECT 8 6 51 52 53 NONE 105
CONECT 9 6 54 55 56 NONE 106
CONECT 10 3 11 57 0 NONE 107
CONECT 11 10 41 12 0 NONE 108
CONECT 12 11 5 13 0 NONE 109
CONECT 13 12 14 0 0 NONE 110
CONECT 14 13 20 36 15 NONE 111
CONECT 15 14 16 41 0 NONE 112
CONECT 16 15 17 40 18 NONE 113
CONECT 18 16 19 20 37 NONE 114
CONECT 20 18 14 21 0 NONE 115
CONECT 21 20 22 58 0 NONE 116
CONECT 22 21 23 35 0 NONE 117
CONECT 23 22 24 59 0 NONE 118
CONECT 24 23 25 29 0 NONE 119
CONECT 25 24 26 27 28 NONE 120
CONECT 26 25 60 61 62 NONE 121
CONECT 27 25 63 64 65 NONE 122
CONECT 28 25 66 67 68 NONE 123
CONECT 29 24 30 69 0 NONE 124
CONECT 30 29 35 31 0 NONE 125
CONECT 31 30 32 33 34 NONE 126
CONECT 32 31 70 71 72 NONE 127
CONECT 33 31 73 74 75 NONE 128
CONECT 34 31 76 77 78 NONE 129
CONECT 35 22 30 36 0 NONE 130
CONECT 36 35 14 0 0 NONE 131
CONECT 37 18 38 79 80 NONE 132
CONECT 38 37 39 81 82 NONE 133
CONECT 39 38 40 83 84 NONE 134
CONECT 40 39 16 85 86 NONE 135
CONECT 41 15 11 87 0 NONE 136
CONECT 42 2 88 89 90 NONE 137
CONECT 43 2 91 92 93 NONE 138
END NONE 139
</inlineContents>
</jmolApplet>
</jmol>

The compound was developed by Professor Jacobsen of Harvard University from around 1990s.

----

==='''Preparation of the catalyst'''===
[[Image: Jacobsen catalyst preparation.gif ]]
----

== Asymmetric Epoxidation of Alkenes ==

[[Image:Jacobsen catalyst epoxidation of alekenes.gif|thumb|Description]]

In the conversion of an alkene to an epoxide, iodosylmesitylene can be used as an oxygen source. The oxygen atom is released onto the manganese(III) ion, with which the oxygen binds forming manganese(V). The oxygen atom can then be delivered to the alkene to form the epoxide.

The delivery method of alkene to oxygen is proposed to occur in a side-on approach, and is consistent with reactivity and enantioselectivity data mainly carried out by J.T. Groves - J. Am. Chem. Soc. 1983, 107, 5791-5796.

The alkene will insert itself next to the manganese centre of the catalyst in such a way
to reduce steric interactions. This is done through a side-on approach, perpendicaular
to the manganese-oxygen bond, with the alkene passing over the chiral carbon and
nitrogen atoms. This is the least hindered method of approach. Approach from the other
side of the catalyst is disfavoured by the dissymmetry of the catalyst.

==='''References'''===
1. Cepanec, I. I. (2001). "An improved method for synthesis of Jacobsen's catalyst." Synthetic communications 31(19): 2913.

2. Flessner, T. T. (1999). "N,N'-bis(3,5-di-t-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride. The Jacobsen catalyst." 341(5): 436.

3. Jacobsen, E. N. E. (1991). "Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane." Journal of the American Chemical Society 113(18): 7063.

4. J. Am. Chem. Soc. 1990, 112, 2801-2803 - asymmetric epoxidation of alkenes.

5. Acc. Chem. Res. 2000, 33, 421-431.

----
==='''Background'''===
Jacobsen's catalyst(1) is made in 1994 by professor Jacobsen, use in converts achiral olefins to chiral epoxides with enantiomeric excesses regularly better than 90% sometime even higher. To date, the selectivity of this reaction has be understood.

[[image:Transformation1.gif]]
(Figure 1)

Jacobsen's Catalyst is a epoxidation catalysts based on a chiral salen ligand complexed with Manganese(III) (the base salen ligand is drawn in red).

[[image:Jacobsen's_Catalyst(1).gif]]

(Figure 2),Jacobsen's Catalyst (1) and the first salen catalyst introduced by Jacobsen (2)

Jacobsen's catalyst is the most convenient and effective compound for stereoselective synthesis in producing the side chain in the antitumour drug Taxol. Jacobsen has reported a simple large-scale preparation of catalyst,making it readily in large quantity. The reaction requires only a small amount of catalylst to substrate while making use of common bleach which is a low cost oxidant.

There are two related but distinct aspects for the reaction, the oxygen transfer and the chiral induction. However neither aspect can be explained fully.

[[image:Cycle1.gif]]

(Figure 3),The epoxidation occurs by a two step catalytic cycle

The oxygen transfer is known to occur by a two step catalytic cycle (Figure 3), similar to the accepted mechanism of metal porphyrin catalysed epoxidations. An oxidant transfers atomic oxygen to the Mn(III) catalyst in the first step. The oxygen presumably coordinates to the metal in a site normal to the porphyrin or salen plane, and the activated oxygen is then delivered to the alkene. This cycle, as opposed to assisted transfer by a complex aggregate, is supported by observations that several oxidants have been used with identical selectivity, that the reaction consumes stoichiometric quantities of an oxidant in the process of converting an alkene to an epoxide, and that related salen complexes show incorporation of oxygen from in situ labelled water, which does not occur via exchange with the oxidant or epoxide.

Oxygen transfer from the catalyst to the olefin has been hypothesized to occur by several different mechanisms (Figure 4) including attack of an oxygen radical intermediate on the double bond (A), concerted oxygen delivery (B), and formation of a metallaoxetane intermediate (C).

[[image:Modesoxtransfer1.gif]]

(Figure 4),Three possible ways of oxygen delivery

Even thought a mechanism which a metallaoxetane is a plausible intermediate is given by Norrby and coworkers, Jacobsen has demonstrated that it is likely oxidation of different olefins occurs by different mechanisms,it is generally accepted that oxygen transfer to olefins with radical stabilizing groups occurs by an attack of an oxygen centred radical on the olefin. This mode of oxygen delivery is supported by the observation that cis olefins result in both cis and trans epoxides.

The second aspect of the epoxidation mechanism must occur in the second step of the catalytic cycle where oxygen is transferred from the oxo-manganese complex to the epoxide. Fundamental to this stereoselection is the relative orientation of the activated catalyst and the olefin in the first irreversible bond formation.

It:Jacobsen

2006-10-26T13:40:25Z

Pdm05:

=='''Jacobsen Catalyst'''==
==='''Introduction'''===
Jacobsen catalyst is the most efficient and commercially available compound among the chiral manganese(III)-salen complexes with the IUPAC name: ''N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexylmanganese(III) chloride''. As the name suggests, the compound is widely used as a catalyst in the epoxidation of olefins for its enantioseletivity.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Jacobsen Catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Jacobsen_catalyst.gif]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexylmanganese(III) chloride''
|-
| [[CAS nummber]]
| 138124-32-0
|-
| [[Chemical formula]]
| {{{formula|C36H52ClMnN2O2
|-
| [[Molecular mass]]
| {{{mol_mass|635.21 g/mol
|-
| [[Simplified molecular input line entry specification|SMILES]]
| {{{SMILES|[Me3C]C(C=C2C(C)(C)C)=CC1=C2O[Mn+3]45[N]([C@H]3[C@H]
([N]4=CC(C=C(C(C)(C)C)C=C6[Me3C])=C6O5)CCCC3)=C1
|-
| [[Colour]]
| {{{Colour| Brown
|-
|}

<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; cpk off;frame 3; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 C 0 -5.987 -2.724 0.763 0.00 0.00 C+0
ATOM 2 C 0 -5.157 -2.243 -0.430 0.00 0.00 C+0
ATOM 3 C 0 -3.953 -1.487 0.069 0.00 0.00 C+0
ATOM 4 C 0 -3.029 -2.117 0.886 0.00 0.00 C+0
ATOM 5 C 0 -1.915 -1.431 1.316 0.00 0.00 C+0
ATOM 6 C 0 -0.915 -2.125 2.205 0.00 0.00 C+0
ATOM 7 C 0 -1.395 -3.547 2.500 0.00 0.00 C+0
ATOM 8 C 0 0.442 -2.181 1.499 0.00 0.00 C+0
ATOM 9 C 0 -0.776 -1.350 3.517 0.00 0.00 C+0
ATOM 10 C 0 -3.768 -0.176 -0.292 0.00 0.00 C+0
ATOM 11 C 0 -2.649 0.553 0.160 0.00 0.00 C+0
ATOM 12 C 0 -1.697 -0.105 0.941 0.00 0.00 C+0
ATOM 13 O 0 -0.457 0.388 1.349 0.00 0.00 O+0
ATOM 14 Mn 0 -0.037 1.374 -0.073 0.00 0.00 Mn+3
ATOM 15 N 0 -1.515 2.546 -0.267 0.00 0.00 N+0
ATOM 16 C 0 -0.898 3.821 -0.006 0.00 0.00 C+0
ATOM 17 H 0 -1.110 4.047 1.039 0.00 0.00 H+0
ATOM 18 C 0 0.645 3.896 -0.139 0.00 0.00 C+0
ATOM 19 H 0 0.866 4.224 -1.154 0.00 0.00 H+0
ATOM 20 N 0 1.363 2.659 0.121 0.00 0.00 N+0
ATOM 21 C 0 2.516 2.124 0.253 0.00 0.00 C+0
ATOM 22 C 0 2.606 0.693 -0.168 0.00 0.00 C+0
ATOM 23 C 0 3.768 0.042 0.299 0.00 0.00 C+0
ATOM 24 C 0 4.040 -1.260 -0.032 0.00 0.00 C+0
ATOM 25 C 0 5.286 -1.927 0.491 0.00 0.00 C+0
ATOM 26 C 0 6.066 -0.938 1.360 0.00 0.00 C+0
ATOM 27 C 0 4.898 -3.147 1.329 0.00 0.00 C+0
ATOM 28 C 0 6.159 -2.372 -0.684 0.00 0.00 C+0
ATOM 29 C 0 3.169 -1.964 -0.848 0.00 0.00 C+0
ATOM 30 C 0 2.020 -1.356 -1.300 0.00 0.00 C+0
ATOM 31 C 0 1.077 -2.126 -2.189 0.00 0.00 C+0
ATOM 32 C 0 1.620 -3.540 -2.405 0.00 0.00 C+0
ATOM 33 C 0 -0.300 -2.204 -1.527 0.00 0.00 C+0
ATOM 34 C 0 0.955 -1.415 -3.539 0.00 0.00 C+0
ATOM 35 C 0 1.711 -0.042 -0.950 0.00 0.00 C+0
ATOM 36 O 0 0.480 0.395 -1.461 0.00 0.00 O+0
ATOM 37 C 0 1.058 5.040 0.808 0.00 0.00 C+0
ATOM 38 C 0 0.492 6.328 0.192 0.00 0.00 C+0
ATOM 39 C 0 -1.021 6.266 0.017 0.00 0.00 C+0
ATOM 40 C 0 -1.434 5.015 -0.798 0.00 0.00 C+0
ATOM 41 C 0 -2.677 2.003 -0.219 0.00 0.00 C+0
ATOM 42 C 0 -4.698 -3.449 -1.252 0.00 0.00 C+0
ATOM 43 C 0 -6.010 -1.323 -1.306 0.00 0.00 C+0
ATOM 44 H 0 -6.313 -1.865 1.348 0.00 0.00 H+0
ATOM 45 H 0 -6.858 -3.271 0.402 0.00 0.00 H+0
ATOM 46 H 0 -5.379 -3.379 1.387 0.00 0.00 H+0
ATOM 47 H 0 -3.182 -3.143 1.186 0.00 0.00 H+0
ATOM 48 H 0 -1.494 -4.099 1.565 0.00 0.00 H+0
ATOM 49 H 0 -0.672 -4.049 3.143 0.00 0.00 H+0
ATOM 50 H 0 -2.361 -3.507 3.003 0.00 0.00 H+0
ATOM 51 H 0 0.709 -1.185 1.146 0.00 0.00 H+0
ATOM 52 H 0 1.200 -2.534 2.198 0.00 0.00 H+0
ATOM 53 H 0 0.382 -2.863 0.651 0.00 0.00 H+0
ATOM 54 H 0 -1.742 -1.311 4.019 0.00 0.00 H+0
ATOM 55 H 0 -0.052 -1.852 4.160 0.00 0.00 H+0
ATOM 56 H 0 -0.433 -0.337 3.306 0.00 0.00 H+0
ATOM 57 H 0 -4.491 0.306 -0.932 0.00 0.00 H+0
ATOM 58 H 0 3.365 2.667 0.640 0.00 0.00 H+0
ATOM 59 H 0 4.458 0.582 0.931 0.00 0.00 H+0
ATOM 60 H 0 5.445 -0.621 2.198 0.00 0.00 H+0
ATOM 61 H 0 6.968 -1.420 1.739 0.00 0.00 H+0
ATOM 62 H 0 6.343 -0.069 0.764 0.00 0.00 H+0
ATOM 63 H 0 4.343 -3.851 0.710 0.00 0.00 H+0
ATOM 64 H 0 5.800 -3.629 1.708 0.00 0.00 H+0
ATOM 65 H 0 4.277 -2.830 2.167 0.00 0.00 H+0
ATOM 66 H 0 6.435 -1.502 -1.281 0.00 0.00 H+0
ATOM 67 H 0 7.060 -2.854 -0.305 0.00 0.00 H+0
ATOM 68 H 0 5.603 -3.076 -1.303 0.00 0.00 H+0
ATOM 69 H 0 3.390 -2.983 -1.128 0.00 0.00 H+0
ATOM 70 H 0 1.708 -4.046 -1.444 0.00 0.00 H+0
ATOM 71 H 0 0.938 -4.096 -3.049 0.00 0.00 H+0
ATOM 72 H 0 2.601 -3.484 -2.877 0.00 0.00 H+0
ATOM 73 H 0 -0.558 -1.230 -1.111 0.00 0.00 H+0
ATOM 74 H 0 -1.044 -2.491 -2.269 0.00 0.00 H+0
ATOM 75 H 0 -0.277 -2.946 -0.729 0.00 0.00 H+0
ATOM 76 H 0 1.936 -1.359 -4.011 0.00 0.00 H+0
ATOM 77 H 0 0.273 -1.971 -4.182 0.00 0.00 H+0
ATOM 78 H 0 0.568 -0.407 -3.385 0.00 0.00 H+0
ATOM 79 H 0 0.632 4.879 1.799 0.00 0.00 H+0
ATOM 80 H 0 2.145 5.100 0.871 0.00 0.00 H+0
ATOM 81 H 0 0.739 7.169 0.840 0.00 0.00 H+0
ATOM 82 H 0 0.954 6.487 -0.782 0.00 0.00 H+0
ATOM 83 H 0 -1.492 6.240 1.000 0.00 0.00 H+0
ATOM 84 H 0 -1.355 7.159 -0.512 0.00 0.00 H+0
ATOM 85 H 0 -1.003 5.059 -1.798 0.00 0.00 H+0
ATOM 86 H 0 -2.521 4.948 -0.858 0.00 0.00 H+0
ATOM 87 H 0 -3.589 2.540 -0.431 0.00 0.00 H+0
ATOM 88 H 0 -5.570 -3.995 -1.612 0.00 0.00 H+0
ATOM 89 H 0 -4.107 -3.106 -2.101 0.00 0.00 H+0
ATOM 90 H 0 -4.091 -4.104 -0.628 0.00 0.00 H+0
ATOM 91 H 0 -6.337 -0.464 -0.720 0.00 0.00 H+0
ATOM 92 H 0 -5.419 -0.980 -2.155 0.00 0.00 H+0
ATOM 93 H 0 -6.881 -1.869 -1.666 0.00 0.00 H+0
CONECT 1 2 44 45 46 NONE 98
CONECT 2 1 3 42 43 NONE 99
CONECT 3 2 4 10 0 NONE 100
CONECT 4 3 5 47 0 NONE 101
CONECT 5 4 12 6 0 NONE 102
CONECT 6 5 7 8 9 NONE 103
CONECT 7 6 48 49 50 NONE 104
CONECT 8 6 51 52 53 NONE 105
CONECT 9 6 54 55 56 NONE 106
CONECT 10 3 11 57 0 NONE 107
CONECT 11 10 41 12 0 NONE 108
CONECT 12 11 5 13 0 NONE 109
CONECT 13 12 14 0 0 NONE 110
CONECT 14 13 20 36 15 NONE 111
CONECT 15 14 16 41 0 NONE 112
CONECT 16 15 17 40 18 NONE 113
CONECT 18 16 19 20 37 NONE 114
CONECT 20 18 14 21 0 NONE 115
CONECT 21 20 22 58 0 NONE 116
CONECT 22 21 23 35 0 NONE 117
CONECT 23 22 24 59 0 NONE 118
CONECT 24 23 25 29 0 NONE 119
CONECT 25 24 26 27 28 NONE 120
CONECT 26 25 60 61 62 NONE 121
CONECT 27 25 63 64 65 NONE 122
CONECT 28 25 66 67 68 NONE 123
CONECT 29 24 30 69 0 NONE 124
CONECT 30 29 35 31 0 NONE 125
CONECT 31 30 32 33 34 NONE 126
CONECT 32 31 70 71 72 NONE 127
CONECT 33 31 73 74 75 NONE 128
CONECT 34 31 76 77 78 NONE 129
CONECT 35 22 30 36 0 NONE 130
CONECT 36 35 14 0 0 NONE 131
CONECT 37 18 38 79 80 NONE 132
CONECT 38 37 39 81 82 NONE 133
CONECT 39 38 40 83 84 NONE 134
CONECT 40 39 16 85 86 NONE 135
CONECT 41 15 11 87 0 NONE 136
CONECT 42 2 88 89 90 NONE 137
CONECT 43 2 91 92 93 NONE 138
END NONE 139
</inlineContents>
</jmolApplet>
</jmol>

The compound was developed by Professor Jacobsen of Harvard University from around 1990s.

----

==='''Preparation of the catalyst'''===
[[Image: Jacobsen catalyst preparation.gif ]]
----

== Asymmetric Epoxidation of Alkenes ==

[[Image:Jacobsen catalyst epoxidation of alekenes.gif|thumb|Description]]

In the conversion of an alkene to an epoxide, iodosylmesitylene can be used as an oxygen source. The oxygen atom is released onto the manganese(III) ion, with which the oxygen binds forming manganese(V). The oxygen atom can then be delivered to the alkene to form the epoxide.

The delivery method of oxygen to the alkene is proposed to occur in a side-on approach, and is consistent with reactivity and enantioselectivity data mainly carried out by J.T. Groves - J. Am. Chem. Soc. 1983, 107, 5791-5796.

==='''References'''===
1. Cepanec, I. I. (2001). "An improved method for synthesis of Jacobsen's catalyst." Synthetic communications 31(19): 2913.

2. Flessner, T. T. (1999). "N,N'-bis(3,5-di-t-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride. The Jacobsen catalyst." 341(5): 436.

3. Jacobsen, E. N. E. (1991). "Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane." Journal of the American Chemical Society 113(18): 7063.

4. J. Am. Chem. Soc. 1990, 112, 2801-2803 - asymmetric epoxidation of alkenes.

5. Acc. Chem. Res. 2000, 33, 421-431.

----
==='''Background'''===
Jacobsen's catalyst(1) is made in 1994 by professor Jacobsen, use in converts achiral olefins to chiral epoxides with enantiomeric excesses regularly better than 90% sometime even higher. To date, the selectivity of this reaction has be understood.

[[image:Transformation1.gif]]
(Figure 1)

Jacobsen's Catalyst is a epoxidation catalysts based on a chiral salen ligand complexed with Manganese(III) (the base salen ligand is drawn in red).

[[image:Jacobsen's_Catalyst(1).gif]]

(Figure 2),Jacobsen's Catalyst (1) and the first salen catalyst introduced by Jacobsen (2)

Jacobsen's catalyst is the most convenient and effective compound for stereoselective synthesis in producing the side chain in the antitumour drug Taxol. Jacobsen has reported a simple large-scale preparation of catalyst,making it readily in large quantity. The reaction requires only a small amount of catalylst to substrate while making use of common bleach which is a low cost oxidant.

There are two related but distinct aspects for the reaction, the oxygen transfer and the chiral induction. However neither aspect can be explained fully.

[[image:Cycle1.gif]]

(Figure 3),The epoxidation occurs by a two step catalytic cycle

The oxygen transfer is known to occur by a two step catalytic cycle (Figure 3), similar to the accepted mechanism of metal porphyrin catalysed epoxidations. An oxidant transfers atomic oxygen to the Mn(III) catalyst in the first step. The oxygen presumably coordinates to the metal in a site normal to the porphyrin or salen plane, and the activated oxygen is then delivered to the alkene. This cycle, as opposed to assisted transfer by a complex aggregate, is supported by observations that several oxidants have been used with identical selectivity, that the reaction consumes stoichiometric quantities of an oxidant in the process of converting an alkene to an epoxide, and that related salen complexes show incorporation of oxygen from in situ labelled water, which does not occur via exchange with the oxidant or epoxide.

Oxygen transfer from the catalyst to the olefin has been hypothesized to occur by several different mechanisms (Figure 4) including attack of an oxygen radical intermediate on the double bond (A), concerted oxygen delivery (B), and formation of a metallaoxetane intermediate (C).

[[image:Modesoxtransfer1.gif]]

(Figure 4),Three possible ways of oxygen delivery

Even thought a mechanism which a metallaoxetane is a plausible intermediate is given by Norrby and coworkers, Jacobsen has demonstrated that it is likely oxidation of different olefins occurs by different mechanisms,it is generally accepted that oxygen transfer to olefins with radical stabilizing groups occurs by an attack of an oxygen centred radical on the olefin. This mode of oxygen delivery is supported by the observation that cis olefins result in both cis and trans epoxides.

The second aspect of the epoxidation mechanism must occur in the second step of the catalytic cycle where oxygen is transferred from the oxo-manganese complex to the epoxide. Fundamental to this stereoselection is the relative orientation of the activated catalyst and the olefin in the first irreversible bond formation.

It:Jacobsen

2006-10-26T13:02:39Z

Pdm05:

=='''Jacobsen Catalyst'''==
==='''Introduction'''===
Jacobsen catalyst is the most efficient and commercially available compound among the chiral manganese(III)-salen complexes with the IUPAC name: ''N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexylmanganese(III) chloride''. As the name suggests, the compound is widely used as a catalyst in the epoxidation of olefins for its enantioseletivity.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Jacobsen Catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Jacobsen_catalyst.gif]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexylmanganese(III) chloride''
|-
| [[CAS nummber]]
| 138124-32-0
|-
| [[Chemical formula]]
| {{{formula|C36H52ClMnN2O2
|-
| [[Molecular mass]]
| {{{mol_mass|635.21 g/mol
|-
| [[Simplified molecular input line entry specification|SMILES]]
| {{{SMILES|[Me3C]C(C=C2C(C)(C)C)=CC1=C2O[Mn+3]45[N]([C@H]3[C@H]
([N]4=CC(C=C(C(C)(C)C)C=C6[Me3C])=C6O5)CCCC3)=C1
|-
| [[Colour]]
| {{{Colour| Brown
|-
|}

<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; cpk off;frame 3; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 C 0 -5.987 -2.724 0.763 0.00 0.00 C+0
ATOM 2 C 0 -5.157 -2.243 -0.430 0.00 0.00 C+0
ATOM 3 C 0 -3.953 -1.487 0.069 0.00 0.00 C+0
ATOM 4 C 0 -3.029 -2.117 0.886 0.00 0.00 C+0
ATOM 5 C 0 -1.915 -1.431 1.316 0.00 0.00 C+0
ATOM 6 C 0 -0.915 -2.125 2.205 0.00 0.00 C+0
ATOM 7 C 0 -1.395 -3.547 2.500 0.00 0.00 C+0
ATOM 8 C 0 0.442 -2.181 1.499 0.00 0.00 C+0
ATOM 9 C 0 -0.776 -1.350 3.517 0.00 0.00 C+0
ATOM 10 C 0 -3.768 -0.176 -0.292 0.00 0.00 C+0
ATOM 11 C 0 -2.649 0.553 0.160 0.00 0.00 C+0
ATOM 12 C 0 -1.697 -0.105 0.941 0.00 0.00 C+0
ATOM 13 O 0 -0.457 0.388 1.349 0.00 0.00 O+0
ATOM 14 Mn 0 -0.037 1.374 -0.073 0.00 0.00 Mn+3
ATOM 15 N 0 -1.515 2.546 -0.267 0.00 0.00 N+0
ATOM 16 C 0 -0.898 3.821 -0.006 0.00 0.00 C+0
ATOM 17 H 0 -1.110 4.047 1.039 0.00 0.00 H+0
ATOM 18 C 0 0.645 3.896 -0.139 0.00 0.00 C+0
ATOM 19 H 0 0.866 4.224 -1.154 0.00 0.00 H+0
ATOM 20 N 0 1.363 2.659 0.121 0.00 0.00 N+0
ATOM 21 C 0 2.516 2.124 0.253 0.00 0.00 C+0
ATOM 22 C 0 2.606 0.693 -0.168 0.00 0.00 C+0
ATOM 23 C 0 3.768 0.042 0.299 0.00 0.00 C+0
ATOM 24 C 0 4.040 -1.260 -0.032 0.00 0.00 C+0
ATOM 25 C 0 5.286 -1.927 0.491 0.00 0.00 C+0
ATOM 26 C 0 6.066 -0.938 1.360 0.00 0.00 C+0
ATOM 27 C 0 4.898 -3.147 1.329 0.00 0.00 C+0
ATOM 28 C 0 6.159 -2.372 -0.684 0.00 0.00 C+0
ATOM 29 C 0 3.169 -1.964 -0.848 0.00 0.00 C+0
ATOM 30 C 0 2.020 -1.356 -1.300 0.00 0.00 C+0
ATOM 31 C 0 1.077 -2.126 -2.189 0.00 0.00 C+0
ATOM 32 C 0 1.620 -3.540 -2.405 0.00 0.00 C+0
ATOM 33 C 0 -0.300 -2.204 -1.527 0.00 0.00 C+0
ATOM 34 C 0 0.955 -1.415 -3.539 0.00 0.00 C+0
ATOM 35 C 0 1.711 -0.042 -0.950 0.00 0.00 C+0
ATOM 36 O 0 0.480 0.395 -1.461 0.00 0.00 O+0
ATOM 37 C 0 1.058 5.040 0.808 0.00 0.00 C+0
ATOM 38 C 0 0.492 6.328 0.192 0.00 0.00 C+0
ATOM 39 C 0 -1.021 6.266 0.017 0.00 0.00 C+0
ATOM 40 C 0 -1.434 5.015 -0.798 0.00 0.00 C+0
ATOM 41 C 0 -2.677 2.003 -0.219 0.00 0.00 C+0
ATOM 42 C 0 -4.698 -3.449 -1.252 0.00 0.00 C+0
ATOM 43 C 0 -6.010 -1.323 -1.306 0.00 0.00 C+0
ATOM 44 H 0 -6.313 -1.865 1.348 0.00 0.00 H+0
ATOM 45 H 0 -6.858 -3.271 0.402 0.00 0.00 H+0
ATOM 46 H 0 -5.379 -3.379 1.387 0.00 0.00 H+0
ATOM 47 H 0 -3.182 -3.143 1.186 0.00 0.00 H+0
ATOM 48 H 0 -1.494 -4.099 1.565 0.00 0.00 H+0
ATOM 49 H 0 -0.672 -4.049 3.143 0.00 0.00 H+0
ATOM 50 H 0 -2.361 -3.507 3.003 0.00 0.00 H+0
ATOM 51 H 0 0.709 -1.185 1.146 0.00 0.00 H+0
ATOM 52 H 0 1.200 -2.534 2.198 0.00 0.00 H+0
ATOM 53 H 0 0.382 -2.863 0.651 0.00 0.00 H+0
ATOM 54 H 0 -1.742 -1.311 4.019 0.00 0.00 H+0
ATOM 55 H 0 -0.052 -1.852 4.160 0.00 0.00 H+0
ATOM 56 H 0 -0.433 -0.337 3.306 0.00 0.00 H+0
ATOM 57 H 0 -4.491 0.306 -0.932 0.00 0.00 H+0
ATOM 58 H 0 3.365 2.667 0.640 0.00 0.00 H+0
ATOM 59 H 0 4.458 0.582 0.931 0.00 0.00 H+0
ATOM 60 H 0 5.445 -0.621 2.198 0.00 0.00 H+0
ATOM 61 H 0 6.968 -1.420 1.739 0.00 0.00 H+0
ATOM 62 H 0 6.343 -0.069 0.764 0.00 0.00 H+0
ATOM 63 H 0 4.343 -3.851 0.710 0.00 0.00 H+0
ATOM 64 H 0 5.800 -3.629 1.708 0.00 0.00 H+0
ATOM 65 H 0 4.277 -2.830 2.167 0.00 0.00 H+0
ATOM 66 H 0 6.435 -1.502 -1.281 0.00 0.00 H+0
ATOM 67 H 0 7.060 -2.854 -0.305 0.00 0.00 H+0
ATOM 68 H 0 5.603 -3.076 -1.303 0.00 0.00 H+0
ATOM 69 H 0 3.390 -2.983 -1.128 0.00 0.00 H+0
ATOM 70 H 0 1.708 -4.046 -1.444 0.00 0.00 H+0
ATOM 71 H 0 0.938 -4.096 -3.049 0.00 0.00 H+0
ATOM 72 H 0 2.601 -3.484 -2.877 0.00 0.00 H+0
ATOM 73 H 0 -0.558 -1.230 -1.111 0.00 0.00 H+0
ATOM 74 H 0 -1.044 -2.491 -2.269 0.00 0.00 H+0
ATOM 75 H 0 -0.277 -2.946 -0.729 0.00 0.00 H+0
ATOM 76 H 0 1.936 -1.359 -4.011 0.00 0.00 H+0
ATOM 77 H 0 0.273 -1.971 -4.182 0.00 0.00 H+0
ATOM 78 H 0 0.568 -0.407 -3.385 0.00 0.00 H+0
ATOM 79 H 0 0.632 4.879 1.799 0.00 0.00 H+0
ATOM 80 H 0 2.145 5.100 0.871 0.00 0.00 H+0
ATOM 81 H 0 0.739 7.169 0.840 0.00 0.00 H+0
ATOM 82 H 0 0.954 6.487 -0.782 0.00 0.00 H+0
ATOM 83 H 0 -1.492 6.240 1.000 0.00 0.00 H+0
ATOM 84 H 0 -1.355 7.159 -0.512 0.00 0.00 H+0
ATOM 85 H 0 -1.003 5.059 -1.798 0.00 0.00 H+0
ATOM 86 H 0 -2.521 4.948 -0.858 0.00 0.00 H+0
ATOM 87 H 0 -3.589 2.540 -0.431 0.00 0.00 H+0
ATOM 88 H 0 -5.570 -3.995 -1.612 0.00 0.00 H+0
ATOM 89 H 0 -4.107 -3.106 -2.101 0.00 0.00 H+0
ATOM 90 H 0 -4.091 -4.104 -0.628 0.00 0.00 H+0
ATOM 91 H 0 -6.337 -0.464 -0.720 0.00 0.00 H+0
ATOM 92 H 0 -5.419 -0.980 -2.155 0.00 0.00 H+0
ATOM 93 H 0 -6.881 -1.869 -1.666 0.00 0.00 H+0
CONECT 1 2 44 45 46 NONE 98
CONECT 2 1 3 42 43 NONE 99
CONECT 3 2 4 10 0 NONE 100
CONECT 4 3 5 47 0 NONE 101
CONECT 5 4 12 6 0 NONE 102
CONECT 6 5 7 8 9 NONE 103
CONECT 7 6 48 49 50 NONE 104
CONECT 8 6 51 52 53 NONE 105
CONECT 9 6 54 55 56 NONE 106
CONECT 10 3 11 57 0 NONE 107
CONECT 11 10 41 12 0 NONE 108
CONECT 12 11 5 13 0 NONE 109
CONECT 13 12 14 0 0 NONE 110
CONECT 14 13 20 36 15 NONE 111
CONECT 15 14 16 41 0 NONE 112
CONECT 16 15 17 40 18 NONE 113
CONECT 18 16 19 20 37 NONE 114
CONECT 20 18 14 21 0 NONE 115
CONECT 21 20 22 58 0 NONE 116
CONECT 22 21 23 35 0 NONE 117
CONECT 23 22 24 59 0 NONE 118
CONECT 24 23 25 29 0 NONE 119
CONECT 25 24 26 27 28 NONE 120
CONECT 26 25 60 61 62 NONE 121
CONECT 27 25 63 64 65 NONE 122
CONECT 28 25 66 67 68 NONE 123
CONECT 29 24 30 69 0 NONE 124
CONECT 30 29 35 31 0 NONE 125
CONECT 31 30 32 33 34 NONE 126
CONECT 32 31 70 71 72 NONE 127
CONECT 33 31 73 74 75 NONE 128
CONECT 34 31 76 77 78 NONE 129
CONECT 35 22 30 36 0 NONE 130
CONECT 36 35 14 0 0 NONE 131
CONECT 37 18 38 79 80 NONE 132
CONECT 38 37 39 81 82 NONE 133
CONECT 39 38 40 83 84 NONE 134
CONECT 40 39 16 85 86 NONE 135
CONECT 41 15 11 87 0 NONE 136
CONECT 42 2 88 89 90 NONE 137
CONECT 43 2 91 92 93 NONE 138
END NONE 139
</inlineContents>
</jmolApplet>
</jmol>

The compound was developed by Professor Jacobsen of Harvard University from around 1990s.

----

==='''Preparation of the catalyst'''===
[[Image: Jacobsen catalyst preparation.gif ]]
----

== Asymmetric Epoxidation of Alkenes ==

[[Image:Jacobsen catalyst epoxidation of alekenes.gif|thumb|Description]]

In the conversion of an alkene to an epoxide, iodosylmesitylene can be used as an oxygen source. The oxygen atom is released onto the manganese(III) ion, with which the oxygen binds forming manganese(IV). The oxygen atom can then be delivered to the alkene to form the epoxide.

==='''References'''===
1. Cepanec, I. I. (2001). "An improved method for synthesis of Jacobsen's catalyst." Synthetic communications 31(19): 2913.

2. Flessner, T. T. (1999). "N,N'-bis(3,5-di-t-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride. The Jacobsen catalyst." 341(5): 436.

3. Jacobsen, E. N. E. (1991). "Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane." Journal of the American Chemical Society 113(18): 7063.

4. J. Am. Chem. Soc. 1990, 112, 2801-2803 - asymmetric epoxidation of alkenes.

5. Acc. Chem. Res. 2000, 33, 421-431.

----
==='''Background'''===
Jacobsen's catalyst(1) is made in 1994 by professor Jacobsen, use in converts achiral olefins to chiral epoxides with enantiomeric excesses regularly better than 90% sometime even higher. To date, the selectivity of this reaction has be understood.

[[image:Transformation1.gif]]
(Figure 1)

Jacobsen's Catalyst is a epoxidation catalysts based on a chiral salen ligand complexed with Manganese(III) (the base salen ligand is drawn in red).

[[image:Jacobsen's_Catalyst(1).gif]]

(Figure 2),Jacobsen's Catalyst (1) and the first salen catalyst introduced by Jacobsen (2)

Jacobsen's catalyst is the most convenient and effective compound for stereoselective synthesis in producing the side chain in the antitumour drug Taxol. Jacobsen has reported a simple large-scale preparation of catalyst,making it readily in large quantity. The reaction requires only a small amount of catalylst to substrate while making use of common bleach which is a low cost oxidant.

There are two related but distinct aspects for the reaction, the oxygen transfer and the chiral induction. However neither aspect can be explained fully.

[[image:Cycle1.gif]]

(Figure 3),The epoxidation occurs by a two step catalytic cycle

The oxygen transfer is known to occur by a two step catalytic cycle (Figure 3), similar to the accepted mechanism of metal porphyrin catalysed epoxidations. An oxidant transfers atomic oxygen to the Mn(III) catalyst in the first step. The oxygen presumably coordinates to the metal in a site normal to the porphyrin or salen plane, and the activated oxygen is then delivered to the alkene. This cycle, as opposed to assisted transfer by a complex aggregate, is supported by observations that several oxidants have been used with identical selectivity, that the reaction consumes stoichiometric quantities of an oxidant in the process of converting an alkene to an epoxide, and that related salen complexes show incorporation of oxygen from in situ labelled water, which does not occur via exchange with the oxidant or epoxide.

Oxygen transfer from the catalyst to the olefin has been hypothesized to occur by several different mechanisms (Figure 4) including attack of an oxygen radical intermediate on the double bond (A), concerted oxygen delivery (B), and formation of a metallaoxetane intermediate (C).

[[image:Modesoxtransfer1.gif]]

(Figure 4),Three possible ways of oxygen delivery

Even thought a mechanism which a metallaoxetane is a plausible intermediate is given by Norrby and coworkers, Jacobsen has demonstrated that it is likely oxidation of different olefins occurs by different mechanisms,it is generally accepted that oxygen transfer to olefins with radical stabilizing groups occurs by an attack of an oxygen centred radical on the olefin. This mode of oxygen delivery is supported by the observation that cis olefins result in both cis and trans epoxides.

The second aspect of the epoxidation mechanism must occur in the second step of the catalytic cycle where oxygen is transferred from the oxo-manganese complex to the epoxide. Fundamental to this stereoselection is the relative orientation of the activated catalyst and the olefin in the first irreversible bond formation.

It:Jacobsen

2006-10-26T11:53:38Z

Pdm05:

=='''Jacobsen Catalyst'''==
==='''Introduction'''===
Jacobsen catalyst is the most efficient and commercially available compound among the chiral manganese(III)-salen complexes with the IUPAC name: ''N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexylmanganese(III) chloride''. As the name suggests, the compound is widely used as a catalyst in the epoxidation of olefins for its enantioseletivity.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Jacobsen Catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Jacobsen_catalyst.gif]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexylmanganese(III) chloride''
|-
| [[CAS nummber]]
| 138124-32-0
|-
| [[Chemical formula]]
| {{{formula|C36H52ClMnN2O2
|-
| [[Molecular mass]]
| {{{mol_mass|635.21 g/mol
|-
| [[Simplified molecular input line entry specification|SMILES]]
| {{{SMILES|[Me3C]C(C=C2C(C)(C)C)=CC1=C2O[Mn+3]45[N]([C@H]3[C@H]
([N]4=CC(C=C(C(C)(C)C)C=C6[Me3C])=C6O5)CCCC3)=C1
|-
| [[Colour]]
| {{{Colour| Brown
|-
|}

<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; cpk off;frame 3; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 C 0 -5.987 -2.724 0.763 0.00 0.00 C+0
ATOM 2 C 0 -5.157 -2.243 -0.430 0.00 0.00 C+0
ATOM 3 C 0 -3.953 -1.487 0.069 0.00 0.00 C+0
ATOM 4 C 0 -3.029 -2.117 0.886 0.00 0.00 C+0
ATOM 5 C 0 -1.915 -1.431 1.316 0.00 0.00 C+0
ATOM 6 C 0 -0.915 -2.125 2.205 0.00 0.00 C+0
ATOM 7 C 0 -1.395 -3.547 2.500 0.00 0.00 C+0
ATOM 8 C 0 0.442 -2.181 1.499 0.00 0.00 C+0
ATOM 9 C 0 -0.776 -1.350 3.517 0.00 0.00 C+0
ATOM 10 C 0 -3.768 -0.176 -0.292 0.00 0.00 C+0
ATOM 11 C 0 -2.649 0.553 0.160 0.00 0.00 C+0
ATOM 12 C 0 -1.697 -0.105 0.941 0.00 0.00 C+0
ATOM 13 O 0 -0.457 0.388 1.349 0.00 0.00 O+0
ATOM 14 Mn 0 -0.037 1.374 -0.073 0.00 0.00 Mn+3
ATOM 15 N 0 -1.515 2.546 -0.267 0.00 0.00 N+0
ATOM 16 C 0 -0.898 3.821 -0.006 0.00 0.00 C+0
ATOM 17 H 0 -1.110 4.047 1.039 0.00 0.00 H+0
ATOM 18 C 0 0.645 3.896 -0.139 0.00 0.00 C+0
ATOM 19 H 0 0.866 4.224 -1.154 0.00 0.00 H+0
ATOM 20 N 0 1.363 2.659 0.121 0.00 0.00 N+0
ATOM 21 C 0 2.516 2.124 0.253 0.00 0.00 C+0
ATOM 22 C 0 2.606 0.693 -0.168 0.00 0.00 C+0
ATOM 23 C 0 3.768 0.042 0.299 0.00 0.00 C+0
ATOM 24 C 0 4.040 -1.260 -0.032 0.00 0.00 C+0
ATOM 25 C 0 5.286 -1.927 0.491 0.00 0.00 C+0
ATOM 26 C 0 6.066 -0.938 1.360 0.00 0.00 C+0
ATOM 27 C 0 4.898 -3.147 1.329 0.00 0.00 C+0
ATOM 28 C 0 6.159 -2.372 -0.684 0.00 0.00 C+0
ATOM 29 C 0 3.169 -1.964 -0.848 0.00 0.00 C+0
ATOM 30 C 0 2.020 -1.356 -1.300 0.00 0.00 C+0
ATOM 31 C 0 1.077 -2.126 -2.189 0.00 0.00 C+0
ATOM 32 C 0 1.620 -3.540 -2.405 0.00 0.00 C+0
ATOM 33 C 0 -0.300 -2.204 -1.527 0.00 0.00 C+0
ATOM 34 C 0 0.955 -1.415 -3.539 0.00 0.00 C+0
ATOM 35 C 0 1.711 -0.042 -0.950 0.00 0.00 C+0
ATOM 36 O 0 0.480 0.395 -1.461 0.00 0.00 O+0
ATOM 37 C 0 1.058 5.040 0.808 0.00 0.00 C+0
ATOM 38 C 0 0.492 6.328 0.192 0.00 0.00 C+0
ATOM 39 C 0 -1.021 6.266 0.017 0.00 0.00 C+0
ATOM 40 C 0 -1.434 5.015 -0.798 0.00 0.00 C+0
ATOM 41 C 0 -2.677 2.003 -0.219 0.00 0.00 C+0
ATOM 42 C 0 -4.698 -3.449 -1.252 0.00 0.00 C+0
ATOM 43 C 0 -6.010 -1.323 -1.306 0.00 0.00 C+0
ATOM 44 H 0 -6.313 -1.865 1.348 0.00 0.00 H+0
ATOM 45 H 0 -6.858 -3.271 0.402 0.00 0.00 H+0
ATOM 46 H 0 -5.379 -3.379 1.387 0.00 0.00 H+0
ATOM 47 H 0 -3.182 -3.143 1.186 0.00 0.00 H+0
ATOM 48 H 0 -1.494 -4.099 1.565 0.00 0.00 H+0
ATOM 49 H 0 -0.672 -4.049 3.143 0.00 0.00 H+0
ATOM 50 H 0 -2.361 -3.507 3.003 0.00 0.00 H+0
ATOM 51 H 0 0.709 -1.185 1.146 0.00 0.00 H+0
ATOM 52 H 0 1.200 -2.534 2.198 0.00 0.00 H+0
ATOM 53 H 0 0.382 -2.863 0.651 0.00 0.00 H+0
ATOM 54 H 0 -1.742 -1.311 4.019 0.00 0.00 H+0
ATOM 55 H 0 -0.052 -1.852 4.160 0.00 0.00 H+0
ATOM 56 H 0 -0.433 -0.337 3.306 0.00 0.00 H+0
ATOM 57 H 0 -4.491 0.306 -0.932 0.00 0.00 H+0
ATOM 58 H 0 3.365 2.667 0.640 0.00 0.00 H+0
ATOM 59 H 0 4.458 0.582 0.931 0.00 0.00 H+0
ATOM 60 H 0 5.445 -0.621 2.198 0.00 0.00 H+0
ATOM 61 H 0 6.968 -1.420 1.739 0.00 0.00 H+0
ATOM 62 H 0 6.343 -0.069 0.764 0.00 0.00 H+0
ATOM 63 H 0 4.343 -3.851 0.710 0.00 0.00 H+0
ATOM 64 H 0 5.800 -3.629 1.708 0.00 0.00 H+0
ATOM 65 H 0 4.277 -2.830 2.167 0.00 0.00 H+0
ATOM 66 H 0 6.435 -1.502 -1.281 0.00 0.00 H+0
ATOM 67 H 0 7.060 -2.854 -0.305 0.00 0.00 H+0
ATOM 68 H 0 5.603 -3.076 -1.303 0.00 0.00 H+0
ATOM 69 H 0 3.390 -2.983 -1.128 0.00 0.00 H+0
ATOM 70 H 0 1.708 -4.046 -1.444 0.00 0.00 H+0
ATOM 71 H 0 0.938 -4.096 -3.049 0.00 0.00 H+0
ATOM 72 H 0 2.601 -3.484 -2.877 0.00 0.00 H+0
ATOM 73 H 0 -0.558 -1.230 -1.111 0.00 0.00 H+0
ATOM 74 H 0 -1.044 -2.491 -2.269 0.00 0.00 H+0
ATOM 75 H 0 -0.277 -2.946 -0.729 0.00 0.00 H+0
ATOM 76 H 0 1.936 -1.359 -4.011 0.00 0.00 H+0
ATOM 77 H 0 0.273 -1.971 -4.182 0.00 0.00 H+0
ATOM 78 H 0 0.568 -0.407 -3.385 0.00 0.00 H+0
ATOM 79 H 0 0.632 4.879 1.799 0.00 0.00 H+0
ATOM 80 H 0 2.145 5.100 0.871 0.00 0.00 H+0
ATOM 81 H 0 0.739 7.169 0.840 0.00 0.00 H+0
ATOM 82 H 0 0.954 6.487 -0.782 0.00 0.00 H+0
ATOM 83 H 0 -1.492 6.240 1.000 0.00 0.00 H+0
ATOM 84 H 0 -1.355 7.159 -0.512 0.00 0.00 H+0
ATOM 85 H 0 -1.003 5.059 -1.798 0.00 0.00 H+0
ATOM 86 H 0 -2.521 4.948 -0.858 0.00 0.00 H+0
ATOM 87 H 0 -3.589 2.540 -0.431 0.00 0.00 H+0
ATOM 88 H 0 -5.570 -3.995 -1.612 0.00 0.00 H+0
ATOM 89 H 0 -4.107 -3.106 -2.101 0.00 0.00 H+0
ATOM 90 H 0 -4.091 -4.104 -0.628 0.00 0.00 H+0
ATOM 91 H 0 -6.337 -0.464 -0.720 0.00 0.00 H+0
ATOM 92 H 0 -5.419 -0.980 -2.155 0.00 0.00 H+0
ATOM 93 H 0 -6.881 -1.869 -1.666 0.00 0.00 H+0
CONECT 1 2 44 45 46 NONE 98
CONECT 2 1 3 42 43 NONE 99
CONECT 3 2 4 10 0 NONE 100
CONECT 4 3 5 47 0 NONE 101
CONECT 5 4 12 6 0 NONE 102
CONECT 6 5 7 8 9 NONE 103
CONECT 7 6 48 49 50 NONE 104
CONECT 8 6 51 52 53 NONE 105
CONECT 9 6 54 55 56 NONE 106
CONECT 10 3 11 57 0 NONE 107
CONECT 11 10 41 12 0 NONE 108
CONECT 12 11 5 13 0 NONE 109
CONECT 13 12 14 0 0 NONE 110
CONECT 14 13 20 36 15 NONE 111
CONECT 15 14 16 41 0 NONE 112
CONECT 16 15 17 40 18 NONE 113
CONECT 18 16 19 20 37 NONE 114
CONECT 20 18 14 21 0 NONE 115
CONECT 21 20 22 58 0 NONE 116
CONECT 22 21 23 35 0 NONE 117
CONECT 23 22 24 59 0 NONE 118
CONECT 24 23 25 29 0 NONE 119
CONECT 25 24 26 27 28 NONE 120
CONECT 26 25 60 61 62 NONE 121
CONECT 27 25 63 64 65 NONE 122
CONECT 28 25 66 67 68 NONE 123
CONECT 29 24 30 69 0 NONE 124
CONECT 30 29 35 31 0 NONE 125
CONECT 31 30 32 33 34 NONE 126
CONECT 32 31 70 71 72 NONE 127
CONECT 33 31 73 74 75 NONE 128
CONECT 34 31 76 77 78 NONE 129
CONECT 35 22 30 36 0 NONE 130
CONECT 36 35 14 0 0 NONE 131
CONECT 37 18 38 79 80 NONE 132
CONECT 38 37 39 81 82 NONE 133
CONECT 39 38 40 83 84 NONE 134
CONECT 40 39 16 85 86 NONE 135
CONECT 41 15 11 87 0 NONE 136
CONECT 42 2 88 89 90 NONE 137
CONECT 43 2 91 92 93 NONE 138
END NONE 139
</inlineContents>
</jmolApplet>
</jmol>

The compound was developed by Professor Jacobsen of Harvard University from around 1990s.

----

==='''Preparation of the catalyst'''===
[[Image: Jacobsen catalyst preparation.gif ]]
----

== Asymmetric Epoxidation of Alkenes ==

[[Image:Jacobsen catalyst epoxidation of alekenes.gif|thumb|Description]]

==='''Reference'''===
1. Cepanec, I. I. (2001). "An improved method for synthesis of Jacobsen's catalyst." Synthetic communications 31(19): 2913.

2. Flessner, T. T. (1999). "N,N'-bis(3,5-di-t-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride. The Jacobsen catalyst." 341(5): 436.

3. Jacobsen, E. N. E. (1991). "Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane." Journal of the American Chemical Society 113(18): 7063.

4. J. Am. Chem. Soc., Vol 112, No. 7. 1990 - asymmetric epoxidation of alkenes.

5. Acc. Chem. Res. 2000, 33, 421-431.

----
==='''Background'''===
Jacobsen's catalyst(1) is made in 1994 by professor Jacobsen, use in converts achiral olefins to chiral epoxides with enantiomeric excesses regularly better than 90% sometime even higher. To date, the selectivity of this reaction has be understood.

[[image:Transformation1.gif]]
(Figure 1)

Jacobsen's Catalyst is a epoxidation catalysts based on a chiral salen ligand complexed with Manganese(III) (the base salen ligand is drawn in red).

[[image:Jacobsen's_Catalyst(1).gif]]

(Figure 2),Jacobsen's Catalyst (1) and the first salen catalyst introduced by Jacobsen (2)

Jacobsen's catalyst is the most convenient and effective compound for stereoselective synthesis in producing the side chain in the antitumour drug Taxol. Jacobsen has reported a simple large-scale preparation of catalyst,making it readily in large quantity. The reaction requires only a small amount of catalylst to substrate while making use of common bleach which is a low cost oxidant.

There are two related but distinct aspects for the reaction, the oxygen transfer and the chiral induction. However neither aspect can be explained fully.

[[image:Cycle1.gif]]

(Figure 3),The epoxidation occurs by a two step catalytic cycle

The oxygen transfer is known to occur by a two step catalytic cycle (Figure 3), similar to the accepted mechanism of metal porphyrin catalysed epoxidations. An oxidant transfers atomic oxygen to the Mn(III) catalyst in the first step. The oxygen presumably coordinates to the metal in a site normal to the porphyrin or salen plane, and the activated oxygen is then delivered to the alkene. This cycle, as opposed to assisted transfer by a complex aggregate, is supported by observations that several oxidants have been used with identical selectivity, that the reaction consumes stoichiometric quantities of an oxidant in the process of converting an alkene to an epoxide, and that related salen complexes show incorporation of oxygen from in situ labelled water, which does not occur via exchange with the oxidant or epoxide.

Oxygen transfer from the catalyst to the olefin has been hypothesized to occur by several different mechanisms (Figure 4) including attack of an oxygen radical intermediate on the double bond (A), concerted oxygen delivery (B), and formation of a metallaoxetane intermediate (C).

[[image:Modesoxtransfer1.gif]]

(Figure 4),Three possible ways of oxygen delivery

Even thought a mechanism which a metallaoxetane is a plausible intermediate is given by Norrby and coworkers, Jacobsen has demonstrated that it is likely oxidation of different olefins occurs by different mechanisms,it is generally accepted that oxygen transfer to olefins with radical stabilizing groups occurs by an attack of an oxygen centred radical on the olefin. This mode of oxygen delivery is supported by the observation that cis olefins result in both cis and trans epoxides.

The second aspect of the epoxidation mechanism must occur in the second step of the catalytic cycle where oxygen is transferred from the oxo-manganese complex to the epoxide. Fundamental to this stereoselection is the relative orientation of the activated catalyst and the olefin in the first irreversible bond formation.

It:Jacobsen

2006-10-24T15:21:12Z

Pdm05:

It:Jacobsen

2006-10-24T15:19:03Z

Pdm05:

File:Jacobsen catalyst epoxidation of alekenes.gif

2006-10-24T14:55:03Z

Pdm05:

It:Sucralose

2006-10-24T13:15:55Z

Pdm05: /* References */

==Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5_stereochemistry.gif]]!!

<jmol>
<jmolApplet>
<size>350</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule
|}

== Properties of Sucralose ==

{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-
5-chloro-6-(hydroxymethyl)oxane-3,4-diol
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|White crystalline powder (40 times their natural size)
[[Image:Sci-of-sucralose.jpg]]

|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|+
|-
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners'''
|-
| sugar
| align="center"|1x
|-
| cyclamate
| align="center"|45x
|-
| aspartame
| align="center"|180x
|-
| saccharin
| align="center"|300x
|-
| '''sucralose'''
| align="center"|'''600x'''
|-
| neotame
| align="center"|13,000x
|}

==Synthesis of Sucralose from Sucrose==

Sucralose is synthesised from the readily available sugar sucrose:

[[Image:Synthesis of sucralose from sucrose.gif]]

The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.

==Sucralose in detail==

===History of Sucralose===
Sucralose, C12H19Cl3O8, 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.

=== Sucralose's low-calorie characteristic ===
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.

=== Safety of Sucralose use? ===
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.

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose

*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)

It:Sucralose

2006-10-24T13:08:55Z

Pdm05: /* References */

It:Sucralose

2006-10-24T12:41:22Z

Pdm05: /* Synthesis of Sucralose from Sucrose */

==Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5_stereochemistry.gif]]!!

<jmol>
<jmolApplet>
<size>350</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-
5-chloro-6-(hydroxymethyl)oxane-3,4-diol
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|White crystalline powder (40 times their natural size)
[[Image:Sci-of-sucralose.jpg]]

|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

==Synthesis of Sucralose from Sucrose==

Sucralose is synthesised from the readily available sugar sucrose:

[[Image:Synthesis of sucralose from sucrose.gif]]

The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.

==Sucralose in detail==

===History of Sucralose===
Sucralose, C12H19Cl3O8, 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.

=== Sucralose's low-calorie characteristic ===
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.

=== Safety of Sucralose use? ===
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.

==The relative potency of sugar compared with artificial sweeteners==

{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners'''
|-
| sugar
| align="center"|1x
|-
| cyclamate
| align="center"|45x
|-
| aspartame
| align="center"|180x
|-
| saccharin
| align="center"|300x
|-
| '''sucralose'''
| align="center"|'''600x'''
|-
| neotame
| align="center"|13,000x
|}

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose

It:Morphine

2006-10-24T12:20:27Z

Pdm05: /* 3D Structure of Morphine */

==Introduction to Morphine==

Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects suc as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.

==3D Structure of Morphine==

<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

==2D Structure of Morphine==

[[Image:200px-Morphine-2D-skeletal.GIF]]

==Uses==

Morphine is used legally:

*analgesic in hospital settings for
*Pain after surgery
*Pain associated with trauma
*In the relief of severe chronic pain
*Cancer pain
*Pain from kidney stones
*Back pain
*In epidural anesthesia
*As an antitussive for severe cough
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS)
*To relieve breathlessness in patients in respiratory failure

==References and External Links==
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine
*Morphine, Molecule of the Month

It:Sucralose

2006-10-24T11:57:25Z

Pdm05: /* Sucralose's low-calorie characteristics */

==Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5_stereochemistry.gif]]!!

<jmol>
<jmolApplet>
<size>350</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-
5-chloro-6-(hydroxymethyl)oxane-3,4-diol
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|White crystalline powder (40 times their natural size)
[[Image:Sci-of-sucralose.jpg]]

|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

==Synthesis of Sucralose from Sucrose==

The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.

[[Image:Synthesis of sucralose from sucrose.gif]]

==History of Sucralose==
Sucralose, C12H19Cl3O8, 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.

== Sucralose's low-calorie characteristic ==
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.

==The relative potency of sugar compared with artificial sweeteners==

{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners'''
|-
| sugar
| align="center"|1x
|-
| cyclamate
| align="center"|45x
|-
| aspartame
| align="center"|180x
|-
| saccharin
| align="center"|300x
|-
| '''sucralose'''
| align="center"|'''600x'''
|-
| neotame
| align="center"|13,000x
|}

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose

It:Sucralose

2006-10-24T11:52:08Z

Pdm05:

==Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5_stereochemistry.gif]]!!

<jmol>
<jmolApplet>
<size>350</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-
5-chloro-6-(hydroxymethyl)oxane-3,4-diol
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|White crystalline powder (40 times their natural size)
[[Image:Sci-of-sucralose.jpg]]

|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

==Synthesis of Sucralose from Sucrose==

The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.

[[Image:Synthesis of sucralose from sucrose.gif]]

==History of Sucralose==
Sucralose, C12H19Cl3O8, 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.

== Sucralose's low-calorie characteristics ==
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.

==The relative potency of sugar compared with artificial sweeteners==

{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners'''
|-
| sugar
| align="center"|1x
|-
| cyclamate
| align="center"|45x
|-
| aspartame
| align="center"|180x
|-
| saccharin
| align="center"|300x
|-
| '''sucralose'''
| align="center"|'''600x'''
|-
| neotame
| align="center"|13,000x
|}

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose

It:Sucralose

2006-10-24T11:50:20Z

Pdm05:

==Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5_stereochemistry.gif]]!!

<jmol>
<jmolApplet>
<size>350</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-
5-chloro-6-(hydroxymethyl)oxane-3,4-diol
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|White crystalline powder (40 times their natural size)
[[Image:Sci-of-sucralose.jpg]]

|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

==Synthesis of Sucralose from Sucrose==

The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.

[[Image:Synthesis of sucralose from sucrose.gif]]

==History of Sucralose==
Sucralose, C12H19Cl3O8, 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.

== Sucralose's low-calorie characteristics ==
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.

==The relative potency of sugar compared with artificial sweeteners==

{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners'''
|-
| sugar
| align="center"|1x
|-
| cyclamate
| align="center"|45x
|-
| aspartame
| align="center"|180x
|-
| saccharin
| align="center"|300x
|-
| '''sucralose'''
| align="center"|'''600x'''
|-
| neotame
| align="center"|13,000x
|}

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose

It:Sucralose

2006-10-24T11:49:27Z

Pdm05:

==Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5_stereochemistry.gif]]!!

<jmol>
<jmolApplet>
<size>350</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-
5-chloro-6-(hydroxymethyl)oxane-3,4-diol
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|White crystalline powder (40 times their natural size)
[[Image:Sci-of-sucralose.jpg]]

|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

==Synthesis of Sucralose from Sucrose==

The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.

[[Image:Synthesis of sucralose from sucrose.gif]]

==History of Sucralose==
Sucralose, C12H19Cl3O8, 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.

== Sucralose low-calorie characteristic ==
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.

==The relative potency of sugar compared with artificial sweeteners==

{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners'''
|-
| sugar
| align="center"|1x
|-
| cyclamate
| align="center"|45x
|-
| aspartame
| align="center"|180x
|-
| saccharin
| align="center"|300x
|-
| '''sucralose'''
| align="center"|'''600x'''
|-
| neotame
| align="center"|13,000x
|}

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose

It:Sucralose

2006-10-23T15:08:06Z

Pdm05:

== Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5_stereochemistry.gif]]!!

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="3" bgcolor="white"|R and S represent the stereocentres of the molecule
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|...
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|White crystalline powder (40 times their natural size)
[[Image:Sci-of-sucralose.jpg]]

|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

==Synthesis Of Sucralose From Sucrose==

The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.

[[Image:Synthesis of sucralose from sucrose.gif]]

==History of Sucralose==
Sucralose, C12H19Cl3O8, 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.

== Sucralose in detail ==
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.

==The relative potency of sugar compared with artificial sweeteners==

{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners'''
|-
| sugar
| align="center"|1x
|-
| cyclamate
| align="center"|45x
|-
| aspartame
| align="center"|180x
|-
| saccharin
| align="center"|300x
|-
| '''sucralose'''
| align="center"|'''600x'''
|-
| neotame
| align="center"|13,000x
|}

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose

It:Sucralose

2006-10-23T15:02:39Z

Pdm05:

== Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5_stereochemistry.gif]]!!

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|...
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|White crystalline powder (40 times their natural size)
[[Image:Sci-of-sucralose.jpg]]

|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

==Synthesis Of Sucralose From Sucrose==

[[Image:Synthesis of sucralose from sucrose.gif]]

==History of Sucralose==
Sucralose, C12H19Cl3O8, 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.

== Sucralose in detail ==
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.

==The relative potency of sugar compared with artificial sweeteners==

{|class="toccolours" border="1" style="fit: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue" |'''Table of potency of artificial sweeteners'''
|-
| sugar
| align="center"|1x
|-
| cyclamate
| align="center"|45x
|-
| aspartame
| align="center"|180x
|-
| saccharin
| align="center"|300x
|-
| '''sucralose'''
| align="center"|'''600x'''
|-
| neotame
| align="center"|13,000x
|}

==The Synthesis Of Sucralose==
The hydroxyl groups in sucrose are replaced by chlorine atoms.
The halogenation with chlorine increases the stability of the molecule.

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

File:Synthesis of sucralose from sucrose.gif

2006-10-23T14:59:49Z

Pdm05:

It:Sucralose

2006-10-23T14:39:43Z

Pdm05: /* Structure of Sucralose */

== Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5_stereochemistry.gif]]!!

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|...
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|White crystalline powder
[[Image:Sci-of-sucralose.jpg]]
(40 times their natural size)

|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

== Sucralose in detail ==
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.

===The relative potency of sugar compared with artificial sweeteners===
{|-sugar 1x
|-cyclamate 45x
|-aspartame 180x
|-saccharin 300x
|-sucralose 600x
|-neotame 13,000x

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

File:Sucralose5 stereochemistry.gif

2006-10-23T14:38:18Z

Pdm05:

It:Sucralose

2006-10-23T13:32:43Z

Pdm05: /* Properties of Sucralose */

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.

== Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5.gif]]!!

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|...
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|...
|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose
*

It:Sucralose

2006-10-23T13:30:41Z

Pdm05: /* References */

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.

== Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5.gif]]!!

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|...
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Apparence
| align="center"|...
|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

== References ==

*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose
*

It:Sucralose

2006-10-23T13:29:50Z

Pdm05: /* Properties of Sucralose */

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.

== Structure of Sucralose ==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|- align="center"
| bgcolor="lt blue"|'''2D Image'''
| bgcolor="lt blue"|'''3D Image'''
|+
! [[Image:Sucralose5.gif]]!!

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="Lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|...
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|130 °C
|-
| Boiling point
| align="center"|... °C
|-
| Apparence
| align="center"|...
|-
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous '''
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

== References ==

1. [http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

It:Sucralose

2006-10-20T15:34:46Z

Pdm05: /* Structure */

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 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.

== Structure ==
{| border="1"
|+
! [[Image:Sucralose5.gif]]!!

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|- align="center"
| '''2D Image'''
| '''3D Image'''
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="white" |'''Table of properties'''
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| Melting point
| align="center"|... °C
|-
| Boiling point
| align="center"|... °C
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

== References ==

1. [http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

It:Sucralose

2006-10-20T15:32:56Z

Pdm05: /* 3D Image of Sucralose */

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 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.

== Structure ==
{| border="1"
|+
! [[Image:Sucralose5.gif]]!!

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|- align="center"
| '''2D Image'''
| '''3D Image'''
|}

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="white" |'''Table of properties'''
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| Melting point
| align="center"|... °C
|-
| Boiling point
| align="center"|... °C
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

== References ==

1. [http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

File:Sucralose5.gif

2006-10-20T15:04:32Z

Pdm05:

File:Sucralose2.gif

2006-10-20T15:02:46Z

Pdm05:

File:Sucralose-real.gif

2006-10-20T15:01:44Z

Pdm05: complete 2D version

complete 2D version

It:Sucralose

2006-10-20T14:54:13Z

Pdm05: /* 3D Image of Sucralose */

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.

== 3D Image of Sucralose ==

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 47
CONECT 2 1 3 32 33 NONE 48
CONECT 3 2 31 4 21 NONE 49
CONECT 4 3 5 0 0 NONE 50
CONECT 5 4 20 6 7 NONE 51
CONECT 7 5 8 9 10 NONE 52
CONECT 9 7 34 0 0 NONE 53
CONECT 10 7 11 12 13 NONE 54
CONECT 12 10 35 0 0 NONE 55
CONECT 13 10 14 15 16 NONE 56
CONECT 14 13 0 0 0 NONE 57
CONECT 16 13 17 18 20 NONE 58
CONECT 18 16 19 36 37 NONE 59
CONECT 19 18 38 0 0 NONE 60
CONECT 20 16 5 0 0 NONE 61
CONECT 21 3 22 23 24 NONE 62
CONECT 23 21 39 0 0 NONE 63
CONECT 24 21 25 26 27 NONE 64
CONECT 26 24 40 0 0 NONE 65
CONECT 27 24 28 29 31 NONE 66
CONECT 29 27 30 41 42 NONE 67
CONECT 30 29 0 0 0 NONE 68
CONECT 31 27 3 0 0 NONE 69
END NONE 70
</inlineContents>
</jmolApplet>
</jmol>

== Properties of Sucralose ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="white" |'''Table of properties'''
|-
| Chemical formula
| align="center"|C12H19Cl3O8
|-
| Molecular weight
| align="center"|398 g/mol
|-
| Melting point
| align="center"|... °C
|-
| Boiling point
| align="center"|... °C
|-
| SMILES
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1
|-
|}

== References ==

1. [http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose

File:Sucralose

2006-10-20T14:42:59Z

Pdm05: 2D structure of sucralose

2D structure of sucralose

File:Sucralose.gif

2006-10-20T14:33:36Z

Pdm05: 1D structure of sucralose

1D structure of sucralose

It:Sucralose

2006-10-20T12:18:51Z

Pdm05:

== 3D Image of Sucralose ==

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 Cl 0 0.492 2.410 0.918 0.00 0.00 Cl+0
ATOM 2 C 0 0.916 0.786 1.578 0.00 0.00 C+0
ATOM 3 C 0 1.176 -0.182 0.422 0.00 0.00 C+0
ATOM 4 O 0 -0.029 -0.387 -0.319 0.00 0.00 O+0
ATOM 5 C 0 -1.027 -0.794 0.619 0.00 0.00 C+0
ATOM 6 H 0 -0.565 -1.395 1.402 0.00 0.00 H+0
ATOM 7 C 0 -2.091 -1.627 -0.100 0.00 0.00 C+0
ATOM 8 H 0 -2.865 -1.920 0.609 0.00 0.00 H+0
ATOM 9 O 0 -1.487 -2.797 -0.657 0.00 0.00 O+0
ATOM 10 C 0 -2.712 -0.785 -1.220 0.00 0.00 C+0
ATOM 11 H 0 -1.961 -0.581 -1.983 0.00 0.00 H+0
ATOM 12 O 0 -3.807 -1.495 -1.803 0.00 0.00 O+0
ATOM 13 C 0 -3.211 0.535 -0.622 0.00 0.00 C+0
ATOM 14 Cl 0 -4.573 0.207 0.513 0.00 0.00 Cl+0
ATOM 15 C 0 -3.691 1.456 -1.745 0.00 0.00 C+0
ATOM 16 C 0 -2.062 1.204 0.136 0.00 0.00 C+0
ATOM 17 H 0 -1.232 1.381 -0.547 0.00 0.00 H+0
ATOM 18 C 0 -2.541 2.539 0.710 0.00 0.00 C+0
ATOM 19 O 0 -1.630 0.360 1.200 0.00 0.00 O+0
ATOM 20 C 0 1.689 -1.528 0.971 0.00 0.00 C+0
ATOM 21 H 0 1.733 -1.503 2.060 0.00 0.00 H+0
ATOM 22 O 0 0.853 -2.599 0.530 0.00 0.00 O+0
ATOM 23 C 0 3.110 -1.664 0.374 0.00 0.00 C+0
ATOM 24 H 0 3.098 -2.287 -0.521 0.00 0.00 H+0
ATOM 25 O 0 4.023 -2.184 1.343 0.00 0.00 O+0
ATOM 26 C 0 3.456 -0.195 0.020 0.00 0.00 C+0
ATOM 27 H 0 3.805 0.341 0.904 0.00 0.00 H+0
ATOM 28 C 0 4.507 -0.141 -1.090 0.00 0.00 C+0
ATOM 29 Cl 0 4.994 1.572 -1.375 0.00 0.00 Cl+0
ATOM 30 O 0 2.196 0.348 -0.440 0.00 0.00 O+0
ATOM 31 H 0 1.813 0.867 2.193 0.00 0.00 H+0
ATOM 32 H 0 0.091 0.415 2.185 0.00 0.00 H+0
ATOM 33 H 0 -1.104 -3.292 0.080 0.00 0.00 H+0
ATOM 34 H 0 -3.448 -2.322 -2.155 0.00 0.00 H+0
ATOM 35 H 0 -4.504 0.974 -2.288 0.00 0.00 H+0
ATOM 36 H 0 -4.046 2.395 -1.318 0.00 0.00 H+0
ATOM 37 H 0 -2.866 1.657 -2.429 0.00 0.00 H+0
ATOM 38 H 0 -3.437 2.377 1.309 0.00 0.00 H+0
ATOM 39 H 0 -1.758 2.968 1.335 0.00 0.00 H+0
ATOM 40 H 0 -2.770 3.225 -0.106 0.00 0.00 H+0
ATOM 41 H 0 1.221 -3.412 0.902 0.00 0.00 H+0
ATOM 42 H 0 4.885 -2.245 0.910 0.00 0.00 H+0
ATOM 43 H 0 5.380 -0.722 -0.793 0.00 0.00 H+0
ATOM 44 H 0 4.089 -0.557 -2.007 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 49
CONECT 2 1 3 31 32 NONE 50
CONECT 3 2 30 4 20 NONE 51
CONECT 4 3 5 0 0 NONE 52
CONECT 5 4 19 6 7 NONE 53
CONECT 7 5 8 9 10 NONE 54
CONECT 9 7 33 0 0 NONE 55
CONECT 10 7 11 12 13 NONE 56
CONECT 12 10 34 0 0 NONE 57
CONECT 13 10 14 15 16 NONE 58
CONECT 14 13 0 0 0 NONE 59
CONECT 15 13 35 36 37 NONE 60
CONECT 16 13 17 18 19 NONE 61
CONECT 18 16 38 39 40 NONE 62
CONECT 19 16 5 0 0 NONE 63
CONECT 20 3 21 22 23 NONE 64
CONECT 22 20 41 0 0 NONE 65
CONECT 23 20 24 25 26 NONE 66
CONECT 25 23 42 0 0 NONE 67
CONECT 26 23 27 28 30 NONE 68
CONECT 28 26 29 43 44 NONE 69
CONECT 29 28 0 0 0 NONE 70
CONECT 30 26 3 0 0 NONE 71
END NONE 72
</inlineContents>
</jmolApplet>
</jmol>