ChemWiki - User contributions [en]

It:Tryptophan

2006-10-29T12:21:29Z

Ll705: /* Dangers previously associated with Tryptophan */

==Introduction==
L-Tryptophan can be thought of as a natural anti-depressant. It is a naturally occuring amino acid that the body takes in through protein foods but can be lost through cooking. It is a precursor for the mood-controlling serotonin, which is a brain neurotransmitter linked with happiness. Tryptophan is one of eight amino acids that cannot be produced by animals. It is the least abundant of the essential amino acids, but it is also one of the most crucial, because of its involvment in the formation of serotonin.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Tryptophan'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:trypt2.gif]]
|-
!{{chembox header}}| General
|-
! Systematic Chemical name
| (S)-2-Amino-3-(1H-indol-3-yl)-
propanoic acid
|-
!Synonyms
| L-Trp; L-Tryptophane; Trp; Tryptophane; 1H-Indole-3-Alanine
|-
!Appearance
|
|-
! Chemical formula
|C<sub>11</sub>H<sub>12</sub>N<sub>2</sub>O<sub>2,</sub>
|-
! Molecular Weight
| 204.23 amu
|-
! CAS number
| 73-22-3
|-
! Smile string
|OC([C@@H](N)CC1=CNC2=CC=CC=C21)=O
|-
!{{chembox header}}| Physical Properties
|-
!Solubility
|Soluble in water
|-
!Melting Point
|280.0-285.0 °C
|-
|}

==3D Molecular Image==
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 4.274 0.812 0.010 0.00 0.00 O+0
ATOM 2 C 0 3.414 -0.215 -0.080 0.00 0.00 C+0
ATOM 3 C 0 1.976 0.037 -0.451 0.00 0.00 C+0
ATOM 4 H 0 1.929 0.798 -1.230 0.00 0.00 H+0
ATOM 5 N 0 1.372 -1.208 -0.945 0.00 0.00 N+0
ATOM 6 C 0 1.209 0.521 0.781 0.00 0.00 C+0
ATOM 7 C 0 -0.198 0.890 0.384 0.00 0.00 C+0
ATOM 8 C 0 -0.642 2.116 0.066 0.00 0.00 C+0
ATOM 9 N 0 -1.974 2.065 -0.241 0.00 0.00 N+0
ATOM 10 C 0 -2.432 0.771 -0.124 0.00 0.00 C+0
ATOM 11 C 0 -3.673 0.174 -0.315 0.00 0.00 C+0
ATOM 12 C 0 -3.818 -1.181 -0.115 0.00 0.00 C+0
ATOM 13 C 0 -2.737 -1.959 0.277 0.00 0.00 C+0
ATOM 14 C 0 -1.509 -1.392 0.470 0.00 0.00 C+0
ATOM 15 C 0 -1.338 -0.022 0.267 0.00 0.00 C+0
ATOM 16 O 0 3.794 -1.342 0.137 0.00 0.00 O+0
ATOM 17 H 0 5.197 0.650 0.248 0.00 0.00 H+0
ATOM 18 H 0 1.437 -1.879 -0.195 0.00 0.00 H+0
ATOM 19 H 0 0.390 -1.020 -1.082 0.00 0.00 H+0
ATOM 20 H 0 1.179 -0.274 1.526 0.00 0.00 H+0
ATOM 21 H 0 1.709 1.394 1.200 0.00 0.00 H+0
ATOM 22 H 0 -0.037 3.011 0.054 0.00 0.00 H+0
ATOM 23 H 0 -2.516 2.826 -0.502 0.00 0.00 H+0
ATOM 24 H 0 -4.521 0.771 -0.619 0.00 0.00 H+0
ATOM 25 H 0 -4.783 -1.643 -0.263 0.00 0.00 H+0
ATOM 26 H 0 -2.868 -3.020 0.430 0.00 0.00 H+0
ATOM 27 H 0 -0.672 -2.004 0.775 0.00 0.00 H+0
CONECT 1 2 17 0 0 NONE 32
CONECT 2 1 3 16 0 NONE 33
CONECT 3 2 4 5 6 NONE 34
CONECT 5 3 18 19 0 NONE 35
CONECT 6 3 7 20 21 NONE 36
CONECT 7 6 15 8 0 NONE 37
CONECT 8 7 9 22 0 NONE 38
CONECT 9 8 10 23 0 NONE 39
CONECT 10 9 15 11 0 NONE 40
CONECT 11 10 12 24 0 NONE 41
CONECT 12 11 13 25 0 NONE 42
CONECT 13 12 14 26 0 NONE 43
CONECT 14 13 15 27 0 NONE 44
CONECT 15 14 10 7 0 NONE 45
CONECT 16 2 0 0 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>

==Medical Uses==
Serotonin deficiency is often associated with depression and obesity, but simply adding it directly to the diet is not effective as it cannot pass the blood-brain barrier. This however can be done by tryptophan's chemical successor 5-hydroxytryptophan and thus an increased intake in tryptophan, which turns into 5-hydroxytryptophan in the body, can counteract the lack of serotonin. Since tryptophan can be cheaply produced and is not regulated as a drug, it is a better alternative to normal antidepressants.

Serotonin deficiency is also associated with obesity, as it has been shown that with excessive levels of sugars and carbohydrate intake as is common for obese people, serotonin is produced. Hence the intake of tryptophan can stimulate serotonin production and the lack of desire for sugar-rich foods.

==Dangers previously associated with Tryptophan==
In 1989 tryptophan supplements were banned as a result of a series of deaths which could be traced back to the intake of tryptophan. However the reason for these deaths was the use of inadequate purification of the substance and the fact that it had been synthesised using a certain type of genetically modified bacteria which produced toxins. No other methods of production produced these toxins and hence the ban has been lifted in several countries. However, tryptophan is still often used by many as an example against the use of genetically engineered products.

==Tryptophan Synthesis==
[[Image:tryptsynthesis.gif]]

==Spectra==
[[Image:massspec2.gif]]

[[Image:IRspectra.gif]]

==References==
*[http://webbook.nist.gov/chemistry/| NIST Chemistry Webbook]
*[http://www.sigmaaldrich.com| Sigma Aldrich]
*[http://www.acdlabs.com/publish/tryptophan/| ACD Labs]

It:Tryptophan

2006-10-29T12:16:01Z

Ll705:

==Introduction==
L-Tryptophan can be thought of as a natural anti-depressant. It is a naturally occuring amino acid that the body takes in through protein foods but can be lost through cooking. It is a precursor for the mood-controlling serotonin, which is a brain neurotransmitter linked with happiness. Tryptophan is one of eight amino acids that cannot be produced by animals. It is the least abundant of the essential amino acids, but it is also one of the most crucial, because of its involvment in the formation of serotonin.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Tryptophan'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:trypt2.gif]]
|-
!{{chembox header}}| General
|-
! Systematic Chemical name
| (S)-2-Amino-3-(1H-indol-3-yl)-
propanoic acid
|-
!Synonyms
| L-Trp; L-Tryptophane; Trp; Tryptophane; 1H-Indole-3-Alanine
|-
!Appearance
|
|-
! Chemical formula
|C<sub>11</sub>H<sub>12</sub>N<sub>2</sub>O<sub>2,</sub>
|-
! Molecular Weight
| 204.23 amu
|-
! CAS number
| 73-22-3
|-
! Smile string
|OC([C@@H](N)CC1=CNC2=CC=CC=C21)=O
|-
!{{chembox header}}| Physical Properties
|-
!Solubility
|Soluble in water
|-
!Melting Point
|280.0-285.0 °C
|-
|}

==3D Molecular Image==
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 4.274 0.812 0.010 0.00 0.00 O+0
ATOM 2 C 0 3.414 -0.215 -0.080 0.00 0.00 C+0
ATOM 3 C 0 1.976 0.037 -0.451 0.00 0.00 C+0
ATOM 4 H 0 1.929 0.798 -1.230 0.00 0.00 H+0
ATOM 5 N 0 1.372 -1.208 -0.945 0.00 0.00 N+0
ATOM 6 C 0 1.209 0.521 0.781 0.00 0.00 C+0
ATOM 7 C 0 -0.198 0.890 0.384 0.00 0.00 C+0
ATOM 8 C 0 -0.642 2.116 0.066 0.00 0.00 C+0
ATOM 9 N 0 -1.974 2.065 -0.241 0.00 0.00 N+0
ATOM 10 C 0 -2.432 0.771 -0.124 0.00 0.00 C+0
ATOM 11 C 0 -3.673 0.174 -0.315 0.00 0.00 C+0
ATOM 12 C 0 -3.818 -1.181 -0.115 0.00 0.00 C+0
ATOM 13 C 0 -2.737 -1.959 0.277 0.00 0.00 C+0
ATOM 14 C 0 -1.509 -1.392 0.470 0.00 0.00 C+0
ATOM 15 C 0 -1.338 -0.022 0.267 0.00 0.00 C+0
ATOM 16 O 0 3.794 -1.342 0.137 0.00 0.00 O+0
ATOM 17 H 0 5.197 0.650 0.248 0.00 0.00 H+0
ATOM 18 H 0 1.437 -1.879 -0.195 0.00 0.00 H+0
ATOM 19 H 0 0.390 -1.020 -1.082 0.00 0.00 H+0
ATOM 20 H 0 1.179 -0.274 1.526 0.00 0.00 H+0
ATOM 21 H 0 1.709 1.394 1.200 0.00 0.00 H+0
ATOM 22 H 0 -0.037 3.011 0.054 0.00 0.00 H+0
ATOM 23 H 0 -2.516 2.826 -0.502 0.00 0.00 H+0
ATOM 24 H 0 -4.521 0.771 -0.619 0.00 0.00 H+0
ATOM 25 H 0 -4.783 -1.643 -0.263 0.00 0.00 H+0
ATOM 26 H 0 -2.868 -3.020 0.430 0.00 0.00 H+0
ATOM 27 H 0 -0.672 -2.004 0.775 0.00 0.00 H+0
CONECT 1 2 17 0 0 NONE 32
CONECT 2 1 3 16 0 NONE 33
CONECT 3 2 4 5 6 NONE 34
CONECT 5 3 18 19 0 NONE 35
CONECT 6 3 7 20 21 NONE 36
CONECT 7 6 15 8 0 NONE 37
CONECT 8 7 9 22 0 NONE 38
CONECT 9 8 10 23 0 NONE 39
CONECT 10 9 15 11 0 NONE 40
CONECT 11 10 12 24 0 NONE 41
CONECT 12 11 13 25 0 NONE 42
CONECT 13 12 14 26 0 NONE 43
CONECT 14 13 15 27 0 NONE 44
CONECT 15 14 10 7 0 NONE 45
CONECT 16 2 0 0 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>

==Medical Uses==
Serotonin deficiency is often associated with depression and obesity, but simply adding it directly to the diet is not effective as it cannot pass the blood-brain barrier. This however can be done by tryptophan's chemical successor 5-hydroxytryptophan and thus an increased intake in tryptophan, which turns into 5-hydroxytryptophan in the body, can counteract the lack of serotonin. Since tryptophan can be cheaply produced and is not regulated as a drug, it is a better alternative to normal antidepressants.

Serotonin deficiency is also associated with obesity, as it has been shown that with excessive levels of sugars and carbohydrate intake as is common for obese people, serotonin is produced. Hence the intake of tryptophan can stimulate serotonin production and the lack of desire for sugar-rich foods.

==Dangers previously associated with Tryptophan==

==Tryptophan Synthesis==
[[Image:tryptsynthesis.gif]]

==Spectra==
[[Image:massspec2.gif]]

[[Image:IRspectra.gif]]

==References==
*[http://webbook.nist.gov/chemistry/| NIST Chemistry Webbook]
*[http://www.sigmaaldrich.com| Sigma Aldrich]
*[http://www.acdlabs.com/publish/tryptophan/| ACD Labs]

It:Tryptophan

2006-10-29T12:13:34Z

Ll705: /* Tryptophan Synthesis */

==Introduction==
L-Tryptophan can be thought of as a natural anti-depressant. It is a naturally occuring amino acid that the body takes in through protein foods but can be lost through cooking. It is a precursor for the mood-controlling serotonin, which is a brain neurotransmitter linked with happiness. Tryptophan is one of eight amino acids that cannot be produced by animals. It is the least abundant of the essential amino acids, but it is also one of the most crucial, because of its involvment in the formation of serotonin.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Tryptophan'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:trypt2.gif]]
|-
!{{chembox header}}| General
|-
! Systematic Chemical name
| (S)-2-Amino-3-(1H-indol-3-yl)-
propanoic acid
|-
!Synonyms
| L-Trp; L-Tryptophane; Trp; Tryptophane; 1H-Indole-3-Alanine
|-
!Appearance
|
|-
! Chemical formula
|C<sub>11</sub>H<sub>12</sub>N<sub>2</sub>O<sub>2,</sub>
|-
! Molecular Weight
| 204.23 amu
|-
! CAS number
| 73-22-3
|-
! Smile string
|OC([C@@H](N)CC1=CNC2=CC=CC=C21)=O
|-
!{{chembox header}}| Physical Properties
|-
!Solubility
|Soluble in water
|-
!Melting Point
|280.0-285.0 °C
|-
|}

==3D Molecular Image==
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 4.274 0.812 0.010 0.00 0.00 O+0
ATOM 2 C 0 3.414 -0.215 -0.080 0.00 0.00 C+0
ATOM 3 C 0 1.976 0.037 -0.451 0.00 0.00 C+0
ATOM 4 H 0 1.929 0.798 -1.230 0.00 0.00 H+0
ATOM 5 N 0 1.372 -1.208 -0.945 0.00 0.00 N+0
ATOM 6 C 0 1.209 0.521 0.781 0.00 0.00 C+0
ATOM 7 C 0 -0.198 0.890 0.384 0.00 0.00 C+0
ATOM 8 C 0 -0.642 2.116 0.066 0.00 0.00 C+0
ATOM 9 N 0 -1.974 2.065 -0.241 0.00 0.00 N+0
ATOM 10 C 0 -2.432 0.771 -0.124 0.00 0.00 C+0
ATOM 11 C 0 -3.673 0.174 -0.315 0.00 0.00 C+0
ATOM 12 C 0 -3.818 -1.181 -0.115 0.00 0.00 C+0
ATOM 13 C 0 -2.737 -1.959 0.277 0.00 0.00 C+0
ATOM 14 C 0 -1.509 -1.392 0.470 0.00 0.00 C+0
ATOM 15 C 0 -1.338 -0.022 0.267 0.00 0.00 C+0
ATOM 16 O 0 3.794 -1.342 0.137 0.00 0.00 O+0
ATOM 17 H 0 5.197 0.650 0.248 0.00 0.00 H+0
ATOM 18 H 0 1.437 -1.879 -0.195 0.00 0.00 H+0
ATOM 19 H 0 0.390 -1.020 -1.082 0.00 0.00 H+0
ATOM 20 H 0 1.179 -0.274 1.526 0.00 0.00 H+0
ATOM 21 H 0 1.709 1.394 1.200 0.00 0.00 H+0
ATOM 22 H 0 -0.037 3.011 0.054 0.00 0.00 H+0
ATOM 23 H 0 -2.516 2.826 -0.502 0.00 0.00 H+0
ATOM 24 H 0 -4.521 0.771 -0.619 0.00 0.00 H+0
ATOM 25 H 0 -4.783 -1.643 -0.263 0.00 0.00 H+0
ATOM 26 H 0 -2.868 -3.020 0.430 0.00 0.00 H+0
ATOM 27 H 0 -0.672 -2.004 0.775 0.00 0.00 H+0
CONECT 1 2 17 0 0 NONE 32
CONECT 2 1 3 16 0 NONE 33
CONECT 3 2 4 5 6 NONE 34
CONECT 5 3 18 19 0 NONE 35
CONECT 6 3 7 20 21 NONE 36
CONECT 7 6 15 8 0 NONE 37
CONECT 8 7 9 22 0 NONE 38
CONECT 9 8 10 23 0 NONE 39
CONECT 10 9 15 11 0 NONE 40
CONECT 11 10 12 24 0 NONE 41
CONECT 12 11 13 25 0 NONE 42
CONECT 13 12 14 26 0 NONE 43
CONECT 14 13 15 27 0 NONE 44
CONECT 15 14 10 7 0 NONE 45
CONECT 16 2 0 0 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>

==Medical Uses==
Serotonin deficiency is often associated with depression and obesity, but simply adding it directly to the diet is not effective as it cannot pass the blood-brain barrier. This however can be done by tryptophan's chemical successor 5-hydroxytryptophan and thus an increased intake in tryptophan, which turns into 5-hydroxytryptophan in the body, can counteract the lack of serotonin. Since tryptophan can be cheaply produced and is not regulated as a drug, it is a better alternative to normal antidepressants.

Serotonin deficiency is also associated with obesity, as it has been shown that with excessive levels of sugars and carbohydrate intake as is common for obese people, serotonin is produced. Hence the intake of tryptophan can stimulate serotonin production and the lack of desire for sugar-rich foods.

==Tryptophan Synthesis==
[[Image:tryptsynthesis.gif]]

==Spectra==
[[Image:massspec2.gif]]

[[Image:IRspectra.gif]]

==References==
*[http://webbook.nist.gov/chemistry/| NIST Chemistry Webbook]
*[http://www.sigmaaldrich.com| Sigma Aldrich]
*[http://www.acdlabs.com/publish/tryptophan/| ACD Labs]

File:Tryptsynthesis.gif

2006-10-29T12:12:28Z

Ll705: synthesis of tryptophan

synthesis of tryptophan

It:Tryptophan

2006-10-27T15:10:48Z

Ll705: /* References */

==Introduction==
L-Tryptophan can be thought of as a natural anti-depressant. It is a naturally occuring amino acid that the body takes in through protein foods but can be lost through cooking. It is a precursor for the mood-controlling serotonin, which is a brain neurotransmitter linked with happiness. Tryptophan is one of eight amino acids that cannot be produced by animals. It is the least abundant of the essential amino acids, but it is also one of the most crucial, because of its involvment in the formation of serotonin.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Tryptophan'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:trypt2.gif]]
|-
!{{chembox header}}| General
|-
! Systematic Chemical name
| (S)-2-Amino-3-(1H-indol-3-yl)-
propanoic acid
|-
!Synonyms
| L-Trp; L-Tryptophane; Trp; Tryptophane; 1H-Indole-3-Alanine
|-
!Appearance
|
|-
! Chemical formula
|C<sub>11</sub>H<sub>12</sub>N<sub>2</sub>O<sub>2,</sub>
|-
! Molecular Weight
| 204.23 amu
|-
! CAS number
| 73-22-3
|-
! Smile string
|OC([C@@H](N)CC1=CNC2=CC=CC=C21)=O
|-
!{{chembox header}}| Physical Properties
|-
!Solubility
|Soluble in water
|-
!Melting Point
|280.0-285.0 °C
|-
|}

==3D Molecular Image==
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 4.274 0.812 0.010 0.00 0.00 O+0
ATOM 2 C 0 3.414 -0.215 -0.080 0.00 0.00 C+0
ATOM 3 C 0 1.976 0.037 -0.451 0.00 0.00 C+0
ATOM 4 H 0 1.929 0.798 -1.230 0.00 0.00 H+0
ATOM 5 N 0 1.372 -1.208 -0.945 0.00 0.00 N+0
ATOM 6 C 0 1.209 0.521 0.781 0.00 0.00 C+0
ATOM 7 C 0 -0.198 0.890 0.384 0.00 0.00 C+0
ATOM 8 C 0 -0.642 2.116 0.066 0.00 0.00 C+0
ATOM 9 N 0 -1.974 2.065 -0.241 0.00 0.00 N+0
ATOM 10 C 0 -2.432 0.771 -0.124 0.00 0.00 C+0
ATOM 11 C 0 -3.673 0.174 -0.315 0.00 0.00 C+0
ATOM 12 C 0 -3.818 -1.181 -0.115 0.00 0.00 C+0
ATOM 13 C 0 -2.737 -1.959 0.277 0.00 0.00 C+0
ATOM 14 C 0 -1.509 -1.392 0.470 0.00 0.00 C+0
ATOM 15 C 0 -1.338 -0.022 0.267 0.00 0.00 C+0
ATOM 16 O 0 3.794 -1.342 0.137 0.00 0.00 O+0
ATOM 17 H 0 5.197 0.650 0.248 0.00 0.00 H+0
ATOM 18 H 0 1.437 -1.879 -0.195 0.00 0.00 H+0
ATOM 19 H 0 0.390 -1.020 -1.082 0.00 0.00 H+0
ATOM 20 H 0 1.179 -0.274 1.526 0.00 0.00 H+0
ATOM 21 H 0 1.709 1.394 1.200 0.00 0.00 H+0
ATOM 22 H 0 -0.037 3.011 0.054 0.00 0.00 H+0
ATOM 23 H 0 -2.516 2.826 -0.502 0.00 0.00 H+0
ATOM 24 H 0 -4.521 0.771 -0.619 0.00 0.00 H+0
ATOM 25 H 0 -4.783 -1.643 -0.263 0.00 0.00 H+0
ATOM 26 H 0 -2.868 -3.020 0.430 0.00 0.00 H+0
ATOM 27 H 0 -0.672 -2.004 0.775 0.00 0.00 H+0
CONECT 1 2 17 0 0 NONE 32
CONECT 2 1 3 16 0 NONE 33
CONECT 3 2 4 5 6 NONE 34
CONECT 5 3 18 19 0 NONE 35
CONECT 6 3 7 20 21 NONE 36
CONECT 7 6 15 8 0 NONE 37
CONECT 8 7 9 22 0 NONE 38
CONECT 9 8 10 23 0 NONE 39
CONECT 10 9 15 11 0 NONE 40
CONECT 11 10 12 24 0 NONE 41
CONECT 12 11 13 25 0 NONE 42
CONECT 13 12 14 26 0 NONE 43
CONECT 14 13 15 27 0 NONE 44
CONECT 15 14 10 7 0 NONE 45
CONECT 16 2 0 0 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>

==Medical Uses==
Serotonin deficiency is often associated with depression and obesity, but simply adding it directly to the diet is not effective as it cannot pass the blood-brain barrier. This however can be done by tryptophan's chemical successor 5-hydroxytryptophan and thus an increased intake in tryptophan, which turns into 5-hydroxytryptophan in the body, can counteract the lack of serotonin. Since tryptophan can be cheaply produced and is not regulated as a drug, it is a better alternative to normal antidepressants.

Serotonin deficiency is also associated with obesity, as it has been shown that with excessive levels of sugars and carbohydrate intake as is common for obese people, serotonin is produced. Hence the intake of tryptophan can stimulate serotonin production and the lack of desire for sugar-rich foods.

==Tryptophan Synthesis==

==Spectra==
[[Image:massspec2.gif]]

[[Image:IRspectra.gif]]

==References==
*[http://webbook.nist.gov/chemistry/| NIST Chemistry Webbook]
*[http://www.sigmaaldrich.com| Sigma Aldrich]
*[http://www.acdlabs.com/publish/tryptophan/| ACD Labs]

It:Tryptophan

2006-10-27T14:48:35Z

Ll705:

==Introduction==
L-Tryptophan can be thought of as a natural anti-depressant. It is a naturally occuring amino acid that the body takes in through protein foods but can be lost through cooking. It is a precursor for the mood-controlling serotonin, which is a brain neurotransmitter linked with happiness. Tryptophan is one of eight amino acids that cannot be produced by animals. It is the least abundant of the essential amino acids, but it is also one of the most crucial, because of its involvment in the formation of serotonin.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Tryptophan'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:trypt2.gif]]
|-
!{{chembox header}}| General
|-
! Systematic Chemical name
| (S)-2-Amino-3-(1H-indol-3-yl)-
propanoic acid
|-
!Synonyms
| L-Trp; L-Tryptophane; Trp; Tryptophane; 1H-Indole-3-Alanine
|-
!Appearance
|
|-
! Chemical formula
|C<sub>11</sub>H<sub>12</sub>N<sub>2</sub>O<sub>2,</sub>
|-
! Molecular Weight
| 204.23 amu
|-
! CAS number
| 73-22-3
|-
! Smile string
|OC([C@@H](N)CC1=CNC2=CC=CC=C21)=O
|-
!{{chembox header}}| Physical Properties
|-
!Solubility
|Soluble in water
|-
!Melting Point
|280.0-285.0 °C
|-
|}

==3D Molecular Image==
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 4.274 0.812 0.010 0.00 0.00 O+0
ATOM 2 C 0 3.414 -0.215 -0.080 0.00 0.00 C+0
ATOM 3 C 0 1.976 0.037 -0.451 0.00 0.00 C+0
ATOM 4 H 0 1.929 0.798 -1.230 0.00 0.00 H+0
ATOM 5 N 0 1.372 -1.208 -0.945 0.00 0.00 N+0
ATOM 6 C 0 1.209 0.521 0.781 0.00 0.00 C+0
ATOM 7 C 0 -0.198 0.890 0.384 0.00 0.00 C+0
ATOM 8 C 0 -0.642 2.116 0.066 0.00 0.00 C+0
ATOM 9 N 0 -1.974 2.065 -0.241 0.00 0.00 N+0
ATOM 10 C 0 -2.432 0.771 -0.124 0.00 0.00 C+0
ATOM 11 C 0 -3.673 0.174 -0.315 0.00 0.00 C+0
ATOM 12 C 0 -3.818 -1.181 -0.115 0.00 0.00 C+0
ATOM 13 C 0 -2.737 -1.959 0.277 0.00 0.00 C+0
ATOM 14 C 0 -1.509 -1.392 0.470 0.00 0.00 C+0
ATOM 15 C 0 -1.338 -0.022 0.267 0.00 0.00 C+0
ATOM 16 O 0 3.794 -1.342 0.137 0.00 0.00 O+0
ATOM 17 H 0 5.197 0.650 0.248 0.00 0.00 H+0
ATOM 18 H 0 1.437 -1.879 -0.195 0.00 0.00 H+0
ATOM 19 H 0 0.390 -1.020 -1.082 0.00 0.00 H+0
ATOM 20 H 0 1.179 -0.274 1.526 0.00 0.00 H+0
ATOM 21 H 0 1.709 1.394 1.200 0.00 0.00 H+0
ATOM 22 H 0 -0.037 3.011 0.054 0.00 0.00 H+0
ATOM 23 H 0 -2.516 2.826 -0.502 0.00 0.00 H+0
ATOM 24 H 0 -4.521 0.771 -0.619 0.00 0.00 H+0
ATOM 25 H 0 -4.783 -1.643 -0.263 0.00 0.00 H+0
ATOM 26 H 0 -2.868 -3.020 0.430 0.00 0.00 H+0
ATOM 27 H 0 -0.672 -2.004 0.775 0.00 0.00 H+0
CONECT 1 2 17 0 0 NONE 32
CONECT 2 1 3 16 0 NONE 33
CONECT 3 2 4 5 6 NONE 34
CONECT 5 3 18 19 0 NONE 35
CONECT 6 3 7 20 21 NONE 36
CONECT 7 6 15 8 0 NONE 37
CONECT 8 7 9 22 0 NONE 38
CONECT 9 8 10 23 0 NONE 39
CONECT 10 9 15 11 0 NONE 40
CONECT 11 10 12 24 0 NONE 41
CONECT 12 11 13 25 0 NONE 42
CONECT 13 12 14 26 0 NONE 43
CONECT 14 13 15 27 0 NONE 44
CONECT 15 14 10 7 0 NONE 45
CONECT 16 2 0 0 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>

==Medical Uses==
Serotonin deficiency is often associated with depression and obesity, but simply adding it directly to the diet is not effective as it cannot pass the blood-brain barrier. This however can be done by tryptophan's chemical successor 5-hydroxytryptophan and thus an increased intake in tryptophan, which turns into 5-hydroxytryptophan in the body, can counteract the lack of serotonin. Since tryptophan can be cheaply produced and is not regulated as a drug, it is a better alternative to normal antidepressants.

Serotonin deficiency is also associated with obesity, as it has been shown that with excessive levels of sugars and carbohydrate intake as is common for obese people, serotonin is produced. Hence the intake of tryptophan can stimulate serotonin production and the lack of desire for sugar-rich foods.

==Tryptophan Synthesis==

==Spectra==
[[Image:massspec2.gif]]

[[Image:IRspectra.gif]]

==References==
*[http://webbook.nist.gov/chemistry/| NIST Chemistry Webbook]
*[http://www.sigmaaldrich.com| Sigma Aldrich]

It:Tryptophan

2006-10-27T14:47:52Z

Ll705: /* Medical Uses */

==Introduction==
L-Tryptophan can be thought of as a natural anti-depressant. It is a naturally occuring amino acid that the body takes in through protein foods but can be lost through cooking. It is a precursor for the mood-controlling serotonin, which is a brain neurotransmitter linked with happiness. Tryptophan is one of eight amino acids that cannot be produced by animals. It is the least abundant of the essential amino acids, but it is also one of the most crucial, because of its involvment in the formation of serotonin.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Tryptophan'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:trypt2.gif]]
|-
!{{chembox header}}| General
|-
! Systematic Chemical name
| (S)-2-Amino-3-(1H-indol-3-yl)-
propanoic acid
|-
!Synonyms
| L-Trp; L-Tryptophane; Trp; Tryptophane; 1H-Indole-3-Alanine
|-
!Appearance
|
|-
! Chemical formula
|C<sub>11</sub>H<sub>12</sub>N<sub>2</sub>O<sub>2,</sub>
|-
! Molecular Weight
| 204.23 amu
|-
! CAS number
| 73-22-3
|-
! Smile string
|OC([C@@H](N)CC1=CNC2=CC=CC=C21)=O
|-
!{{chembox header}}| Physical Properties
|-
!Solubility
|Soluble in water
|-
!Melting Point
|280.0-285.0 °C
|-
|}

==3D Molecular Image==
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 4.274 0.812 0.010 0.00 0.00 O+0
ATOM 2 C 0 3.414 -0.215 -0.080 0.00 0.00 C+0
ATOM 3 C 0 1.976 0.037 -0.451 0.00 0.00 C+0
ATOM 4 H 0 1.929 0.798 -1.230 0.00 0.00 H+0
ATOM 5 N 0 1.372 -1.208 -0.945 0.00 0.00 N+0
ATOM 6 C 0 1.209 0.521 0.781 0.00 0.00 C+0
ATOM 7 C 0 -0.198 0.890 0.384 0.00 0.00 C+0
ATOM 8 C 0 -0.642 2.116 0.066 0.00 0.00 C+0
ATOM 9 N 0 -1.974 2.065 -0.241 0.00 0.00 N+0
ATOM 10 C 0 -2.432 0.771 -0.124 0.00 0.00 C+0
ATOM 11 C 0 -3.673 0.174 -0.315 0.00 0.00 C+0
ATOM 12 C 0 -3.818 -1.181 -0.115 0.00 0.00 C+0
ATOM 13 C 0 -2.737 -1.959 0.277 0.00 0.00 C+0
ATOM 14 C 0 -1.509 -1.392 0.470 0.00 0.00 C+0
ATOM 15 C 0 -1.338 -0.022 0.267 0.00 0.00 C+0
ATOM 16 O 0 3.794 -1.342 0.137 0.00 0.00 O+0
ATOM 17 H 0 5.197 0.650 0.248 0.00 0.00 H+0
ATOM 18 H 0 1.437 -1.879 -0.195 0.00 0.00 H+0
ATOM 19 H 0 0.390 -1.020 -1.082 0.00 0.00 H+0
ATOM 20 H 0 1.179 -0.274 1.526 0.00 0.00 H+0
ATOM 21 H 0 1.709 1.394 1.200 0.00 0.00 H+0
ATOM 22 H 0 -0.037 3.011 0.054 0.00 0.00 H+0
ATOM 23 H 0 -2.516 2.826 -0.502 0.00 0.00 H+0
ATOM 24 H 0 -4.521 0.771 -0.619 0.00 0.00 H+0
ATOM 25 H 0 -4.783 -1.643 -0.263 0.00 0.00 H+0
ATOM 26 H 0 -2.868 -3.020 0.430 0.00 0.00 H+0
ATOM 27 H 0 -0.672 -2.004 0.775 0.00 0.00 H+0
CONECT 1 2 17 0 0 NONE 32
CONECT 2 1 3 16 0 NONE 33
CONECT 3 2 4 5 6 NONE 34
CONECT 5 3 18 19 0 NONE 35
CONECT 6 3 7 20 21 NONE 36
CONECT 7 6 15 8 0 NONE 37
CONECT 8 7 9 22 0 NONE 38
CONECT 9 8 10 23 0 NONE 39
CONECT 10 9 15 11 0 NONE 40
CONECT 11 10 12 24 0 NONE 41
CONECT 12 11 13 25 0 NONE 42
CONECT 13 12 14 26 0 NONE 43
CONECT 14 13 15 27 0 NONE 44
CONECT 15 14 10 7 0 NONE 45
CONECT 16 2 0 0 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>

==Medical Uses==
Serotonin deficiency is often associated with depression and obesity, but simply adding it directly to the diet is not effective as it cannot pass the blood-brain barrier. This however can be done by tryptophan's chemical successor 5-hydroxytryptophan and thus an increased intake in tryptophan, which turns into 5-hydroxytryptophan in the body, can counteract the lack of serotonin. Since tryptophan can be cheaply produced and is not regulated as a drug, it is a better alternative to normal antidepressants.

Serotonin deficiency is also associated with obesity, as it has been shown that with excessive levels of sugars and carbohydrate intake as is common for obese people, serotonin is produced. Hence the intake of tryptophan can stimulate serotonin production and the lack of desire for sugar-rich foods.

==Spectra==
[[Image:massspec2.gif]]

[[Image:IRspectra.gif]]

==References==
*[http://webbook.nist.gov/chemistry/| NIST Chemistry Webbook]
*[http://www.sigmaaldrich.com| Sigma Aldrich]

It:Tryptophan

2006-10-27T14:40:38Z

Ll705:

==Introduction==
L-Tryptophan can be thought of as a natural anti-depressant. It is a naturally occuring amino acid that the body takes in through protein foods but can be lost through cooking. It is a precursor for the mood-controlling serotonin, which is a brain neurotransmitter linked with happiness. Tryptophan is one of eight amino acids that cannot be produced by animals. It is the least abundant of the essential amino acids, but it is also one of the most crucial, because of its involvment in the formation of serotonin.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Tryptophan'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:trypt2.gif]]
|-
!{{chembox header}}| General
|-
! Systematic Chemical name
| (S)-2-Amino-3-(1H-indol-3-yl)-
propanoic acid
|-
!Synonyms
| L-Trp; L-Tryptophane; Trp; Tryptophane; 1H-Indole-3-Alanine
|-
!Appearance
|
|-
! Chemical formula
|C<sub>11</sub>H<sub>12</sub>N<sub>2</sub>O<sub>2,</sub>
|-
! Molecular Weight
| 204.23 amu
|-
! CAS number
| 73-22-3
|-
! Smile string
|OC([C@@H](N)CC1=CNC2=CC=CC=C21)=O
|-
!{{chembox header}}| Physical Properties
|-
!Solubility
|Soluble in water
|-
!Melting Point
|280.0-285.0 °C
|-
|}

==3D Molecular Image==
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 4.274 0.812 0.010 0.00 0.00 O+0
ATOM 2 C 0 3.414 -0.215 -0.080 0.00 0.00 C+0
ATOM 3 C 0 1.976 0.037 -0.451 0.00 0.00 C+0
ATOM 4 H 0 1.929 0.798 -1.230 0.00 0.00 H+0
ATOM 5 N 0 1.372 -1.208 -0.945 0.00 0.00 N+0
ATOM 6 C 0 1.209 0.521 0.781 0.00 0.00 C+0
ATOM 7 C 0 -0.198 0.890 0.384 0.00 0.00 C+0
ATOM 8 C 0 -0.642 2.116 0.066 0.00 0.00 C+0
ATOM 9 N 0 -1.974 2.065 -0.241 0.00 0.00 N+0
ATOM 10 C 0 -2.432 0.771 -0.124 0.00 0.00 C+0
ATOM 11 C 0 -3.673 0.174 -0.315 0.00 0.00 C+0
ATOM 12 C 0 -3.818 -1.181 -0.115 0.00 0.00 C+0
ATOM 13 C 0 -2.737 -1.959 0.277 0.00 0.00 C+0
ATOM 14 C 0 -1.509 -1.392 0.470 0.00 0.00 C+0
ATOM 15 C 0 -1.338 -0.022 0.267 0.00 0.00 C+0
ATOM 16 O 0 3.794 -1.342 0.137 0.00 0.00 O+0
ATOM 17 H 0 5.197 0.650 0.248 0.00 0.00 H+0
ATOM 18 H 0 1.437 -1.879 -0.195 0.00 0.00 H+0
ATOM 19 H 0 0.390 -1.020 -1.082 0.00 0.00 H+0
ATOM 20 H 0 1.179 -0.274 1.526 0.00 0.00 H+0
ATOM 21 H 0 1.709 1.394 1.200 0.00 0.00 H+0
ATOM 22 H 0 -0.037 3.011 0.054 0.00 0.00 H+0
ATOM 23 H 0 -2.516 2.826 -0.502 0.00 0.00 H+0
ATOM 24 H 0 -4.521 0.771 -0.619 0.00 0.00 H+0
ATOM 25 H 0 -4.783 -1.643 -0.263 0.00 0.00 H+0
ATOM 26 H 0 -2.868 -3.020 0.430 0.00 0.00 H+0
ATOM 27 H 0 -0.672 -2.004 0.775 0.00 0.00 H+0
CONECT 1 2 17 0 0 NONE 32
CONECT 2 1 3 16 0 NONE 33
CONECT 3 2 4 5 6 NONE 34
CONECT 5 3 18 19 0 NONE 35
CONECT 6 3 7 20 21 NONE 36
CONECT 7 6 15 8 0 NONE 37
CONECT 8 7 9 22 0 NONE 38
CONECT 9 8 10 23 0 NONE 39
CONECT 10 9 15 11 0 NONE 40
CONECT 11 10 12 24 0 NONE 41
CONECT 12 11 13 25 0 NONE 42
CONECT 13 12 14 26 0 NONE 43
CONECT 14 13 15 27 0 NONE 44
CONECT 15 14 10 7 0 NONE 45
CONECT 16 2 0 0 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>

==Medical Uses==
Serotonin deficiency is often associated with depression and obesity, but simply adding it directly to the diet is not effective as it cannot pass the blood-brain barrier. This however can be done by tryptophan's chemical successor 5-hydroxytryptophan and thus an increased intake in tryptophan, which turns into 5-hydroxytryptophan in the body, can counteract the lack of serotonin.

==Spectra==
[[Image:massspec2.gif]]

[[Image:IRspectra.gif]]

==References==
*[http://webbook.nist.gov/chemistry/| NIST Chemistry Webbook]
*[http://www.sigmaaldrich.com| Sigma Aldrich]

It:Tryptophan

2006-10-27T14:34:56Z

Ll705: /* Introduction */

It:Tryptophan

2006-10-26T16:51:29Z

Ll705: /* References */

It:Tryptophan

2006-10-26T16:50:04Z

Ll705:

It:Tryptophan

2006-10-26T16:49:19Z

Ll705:

It:Tryptophan

2006-10-26T16:23:26Z

Ll705: /* Introduction */

It:Tryptophan

2006-10-26T16:17:51Z

Ll705:

==Introduction==

==Molecular Images==
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 4.274 0.812 0.010 0.00 0.00 O+0
ATOM 2 C 0 3.414 -0.215 -0.080 0.00 0.00 C+0
ATOM 3 C 0 1.976 0.037 -0.451 0.00 0.00 C+0
ATOM 4 H 0 1.929 0.798 -1.230 0.00 0.00 H+0
ATOM 5 N 0 1.372 -1.208 -0.945 0.00 0.00 N+0
ATOM 6 C 0 1.209 0.521 0.781 0.00 0.00 C+0
ATOM 7 C 0 -0.198 0.890 0.384 0.00 0.00 C+0
ATOM 8 C 0 -0.642 2.116 0.066 0.00 0.00 C+0
ATOM 9 N 0 -1.974 2.065 -0.241 0.00 0.00 N+0
ATOM 10 C 0 -2.432 0.771 -0.124 0.00 0.00 C+0
ATOM 11 C 0 -3.673 0.174 -0.315 0.00 0.00 C+0
ATOM 12 C 0 -3.818 -1.181 -0.115 0.00 0.00 C+0
ATOM 13 C 0 -2.737 -1.959 0.277 0.00 0.00 C+0
ATOM 14 C 0 -1.509 -1.392 0.470 0.00 0.00 C+0
ATOM 15 C 0 -1.338 -0.022 0.267 0.00 0.00 C+0
ATOM 16 O 0 3.794 -1.342 0.137 0.00 0.00 O+0
ATOM 17 H 0 5.197 0.650 0.248 0.00 0.00 H+0
ATOM 18 H 0 1.437 -1.879 -0.195 0.00 0.00 H+0
ATOM 19 H 0 0.390 -1.020 -1.082 0.00 0.00 H+0
ATOM 20 H 0 1.179 -0.274 1.526 0.00 0.00 H+0
ATOM 21 H 0 1.709 1.394 1.200 0.00 0.00 H+0
ATOM 22 H 0 -0.037 3.011 0.054 0.00 0.00 H+0
ATOM 23 H 0 -2.516 2.826 -0.502 0.00 0.00 H+0
ATOM 24 H 0 -4.521 0.771 -0.619 0.00 0.00 H+0
ATOM 25 H 0 -4.783 -1.643 -0.263 0.00 0.00 H+0
ATOM 26 H 0 -2.868 -3.020 0.430 0.00 0.00 H+0
ATOM 27 H 0 -0.672 -2.004 0.775 0.00 0.00 H+0
CONECT 1 2 17 0 0 NONE 32
CONECT 2 1 3 16 0 NONE 33
CONECT 3 2 4 5 6 NONE 34
CONECT 5 3 18 19 0 NONE 35
CONECT 6 3 7 20 21 NONE 36
CONECT 7 6 15 8 0 NONE 37
CONECT 8 7 9 22 0 NONE 38
CONECT 9 8 10 23 0 NONE 39
CONECT 10 9 15 11 0 NONE 40
CONECT 11 10 12 24 0 NONE 41
CONECT 12 11 13 25 0 NONE 42
CONECT 13 12 14 26 0 NONE 43
CONECT 14 13 15 27 0 NONE 44
CONECT 15 14 10 7 0 NONE 45
CONECT 16 2 0 0 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>

[[Image:trypt2.gif]]

==Spectra==
[[Image:massspec2.gif]]

[[Image:IRspectra.gif]]

==References==
*[http://webbook.nist.gov/chemistry/| NIST Chemistry Webbook]

File:IRspectra.gif

2006-10-26T16:15:35Z

Ll705: IR spectrum

IR spectrum

It:Tryptophan

2006-10-26T16:14:46Z

Ll705:

File:Massspec2.gif

2006-10-26T16:14:11Z

Ll705: mass spectrum

mass spectrum

File:Trypt2.gif

2006-10-26T16:12:28Z

Ll705: tryptophan molecule

tryptophan molecule

It:projects

2006-10-26T16:08:33Z

Ll705: /* Supplemental Project Page */

__FORCETOC__

'''''You MUST use the Edit buttons on the right to edit this content. Do NOT use the Edit button on the top of this page.'''''
== Sandbox (Play-Pen) ==

This is an area where you can play without worrying what you do. Enter it by pressing the [Edit] button '''on the right''' and '''not''' at the top. Go here for a [http://en.wikipedia.org/wiki/Wikipedia:Cheatsheet ''cheat sheet''] summary of how to create a Wiki page. It's a free-for-all in here! Learn how to use a Wiki by coming here! PS This is how to do Greek: Α, α, β Δ, δ
Try copying/pasting some of the [http://www.ch.ic.ac.uk/local/it/lab1.html examples in the course work] into this page. See the effect by selecting '''Show Preview'''. No not use '''Save Page''' so as to leave this area uncluttered for others.
----
<div align="left"><br>

== Main Project Page ==
'''Please do not edit this page itself'''. Click on one of the titles to start editing.
{| summary="CIT Project Titles" border="1"
! bgcolor="cyan" |Project<br /> Number
! bgcolor="cyan" |General Keywords
|-
| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
| bgcolor="#CCFF00" |02
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]
|-
| bgcolor="#CCFF00" |03
| bgcolor="#CCFF00" | [[it:Rapamycin|Rapamycin (prevents transplant rejection)]]
|-
| bgcolor="#CCFF00" |04
| bgcolor="#66FF99" | [[it:Gossypol|Gossypol (male birth control)]]
|-
| bgcolor="#CCFF00" |05
| bgcolor="#CCFF00" | [[it:Gentamycin|Gentamicin A (aminoglycoside antibiotic)]]
|-
| bgcolor="#CCFF00" |06
| bgcolor="#66FF99" | [[it:Herceptin|Herceptin (topical anticancer drug)]]
|-
| bgcolor="#CCFF00" |07
| bgcolor="#CCFF00" | [[it:Gingerone|Zingerone (the characteristic smell of ginger)]]
|-
| bgcolor="#CCFF00" |08
| bgcolor="#66FF99" | [[it:Sucralose|Sucralose (non-metabolizable sweetening agent)]]
|-
| bgcolor="#CCFF00" |09
| bgcolor="#CCFF00" | [[it:Bufotoxin|Bufotoxin (active component of the toad ''Bufo vulgaris'')]]
|-
| bgcolor="#CCFF00" |10
| bgcolor="#66FF99" | [[it:Roaccutane|Roaccutane (treatment for severe acne)]]
|-
| bgcolor="#CCFF00" |11
| bgcolor="#CCFF00" | [[it:Sibutramine|Sibutramine (appetite suppresor)]]
|-
| bgcolor="#CCFF00" |12
| bgcolor="#66FF99" | [[it:Anandamide|Anandamide (the "feel-good" factor in chocolate)]]
|-
| bgcolor="#CCFF00" |13
| bgcolor="#CCFF00" | [[it:h3nbh3|Ammonia-borane: H<sub>3</sub>N-BH<sub>3</sub> (Hydrogen storage molecule?)]]
|-
| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
|-
| bgcolor="#CCFF00" |15
| bgcolor="#CCFF00" | [[it:Hycocine|Hyoscine (From Mandrake and Witches Henbane, pre-med before surgery)]]
|-
| bgcolor="#CCFF00" |16
| bgcolor="#66FF99" | [[it:Capreomycin|Capreomycin (Drug-resistant TB)]]
|-
| bgcolor="#CCFF00" |17
| bgcolor="#CCFF00" | [[it:wilkinson|Wilkinson's catalyst]]
|-
| bgcolor="#CCFF00" |18
| bgcolor="#66FF99" | [[it:Jacobsen|Jacobsen's epoxidation catalyst]]
|-
| bgcolor="#CCFF00" |19
| bgcolor="#CCFF00" | [[it:Methylaluminoxane|Methylaluminoxane: MAO - hugely important ethylene polymerisation cocatalyst]]
|-
| bgcolor="#CCFF00" |20
| bgcolor="#66FF99" | [[it:Schwartz|Schwartz reagent for the hydrozirconation of alkenes and alkynes]]
|}

== Supplemental Project Page ==

This area is for people who wish to create their own projects if none of the above appeal to them. Click on the '''Edit''' button to the right to open up an editable page,
then add an entry below as follows

*<nowiki> [[it:name_of_project|Descriptive name of intended project]]</nowiki>
*This will produce the effect: [[it:name_of_project|Descriptive name of intended project]]
----
*[[it:sitagliptin_page|Sitagliptin]]
*[[it:Retinal|Retinal, molecule of sight]]
*[[it:Tamoxifen|Tamoxifen, breast cancer treatment]]
*[[it:Morphine|Morphine, painkiller]]
*[[it:Pelargonidin|Pelargonidin, colouring in nature]]
*[[it:Propanil|Propanil, weedkiller]]
*[[it:Ranitidine|Ranitidine, antiulcerative]]
*[[it:chlorphentermine|chlorphentermine, anorectic]]
*[[it:Serotonin|Serotonin, The 'HAPPY' Drug]]
*[[it:Amphidinolide T1|Amphidinolide T1]]
*[[it:Rosiglitazone|Rosiglitazone, drug that is currently used to treat diabetes.]]
*[[it:Furosemide|Furosemide]]
*[[it:Tryptophan|Tryptophan]]

== [[Special:Export|Export Pages]] ==

This takes you to an '''Export''' page. A backup of the Projects area can be made (in XML) if you want to keep your own
''snapshot'' of the project pages at any instant. After you Export the page you want (ie '''It:projects''' or '''It:Lignocaine''' for example) the XML encoding of it will appear in your browser Window. You should '''view source''' for this material, copy it to a text editor, and thence save it to disk.

== Overlaps ==

If two people start editing a page at the same time, and '''save''' the change simultaneously, its possible only one of the changes
will be made permanent. If anyone spots this happening, please let me know.

One precaution you could take is to keep a copy of the contents of the page you are editing in eg Wordpad (or Word),
make the changes there, and then copy the entire lot to the Wiki page to preview and then save. Tht way, if your contribution
is overlapped by someone else, you will still have a copy, and you can then resubmit it.
----
--[[User:Rzepa|Rzepa]] 12:25, 19 October 2006 (BST)

== Wiki Utillities ==
Utilities have been written to help the conversion of material from HTML.

# [http://diberri.dyndns.org/wikipedia/html2wiki/ A HTML2Wiki Converter]

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=== Wiki Templates ===

[[Template:DOI]] and [[Template:Doi-inline]] are providea as (protected) templates for your use. Many other templates exist, often to be found on e.g. Wikipedia pages. You may decide one of these is of particular use, or of interest. If so, you can install it on the wiki here for you and others to use. Add below a line that looks like {{template-name|parameter}}, save, and click on the red text to create the new template. If you prefer the task of adding useful templates to that of adding information about molecules, then you will be given full credit for performing this valuable service for others!
--[[User:Rzepa|Rzepa]] 14:41, 20 October 2006 (BST)

----
[[Template:Chem-Data]]

It:Piperine

2006-10-25T09:47:15Z

Ll705:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" | 40mg/L @ 219K [http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341]
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135<sup>o</sup>C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; 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 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. [http://en.wikipedia.org/wiki/Thermogenesis Thermogenesis] is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

It:Piperine

2006-10-25T09:36:25Z

Ll705:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" | 40mg/L @ 219K [http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341]
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135<sup>o</sup>C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; 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 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. Thermogenesis is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

It:Piperine

2006-10-25T09:27:48Z

Ll705:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" | 40mg/L @ 219K [http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341]
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135<sup>o</sup>C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; 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 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

File:Cbook.gif

2006-10-25T09:26:33Z

Ll705: mass spectrum of piperine

mass spectrum of piperine

It:Piperine

2006-10-25T09:23:16Z

Ll705: /* Introduction */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" | 40mg/L @ 219K [http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341]
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135<sup>o</sup>C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; 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 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

It:Piperine

2006-10-25T09:20:31Z

Ll705:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" | 40mg/L @ 219K [http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341]
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135<sup>o</sup>C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; 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 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

It:Piperine

2006-10-25T09:18:41Z

Ll705:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" | 40mg/L @ 219K [http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341]
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135<sup>o</sup>C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion.

[[Image:piperine.gif]]
<div align="left"><br>
== '''Properties of Piperine''' ==
</div>
{| border="1"
|+
! Property !! Value !!
|-
! Molecular Formula
| C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub> ||
|-
! Molecular Weight
|285.34 amu ||
|-
! Melting Point
|131-135°C||
|}

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; 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 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

File:Piperine2.gif

2006-10-25T09:15:08Z

Ll705: synthesis of piperine

synthesis of piperine

It:Piperine

2006-10-19T14:58:31Z

Ll705:

[[Image:piperine.gif]]
<div align="left"><br>
== '''Properties of Piperine''' ==
</div>
{| border="1"
|+
! Property !! Value !!
|-
! Molecular Formula
| C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub> ||
|-
! Molecular Weight
|285.34 amu ||
|-
! Melting Point
|131-135°C||
|}

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; 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 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

File:Massspec.gif

2006-10-19T14:39:15Z

Ll705: mass spectrum of piperine

mass spectrum of piperine

It:Piperine

2006-10-19T14:28:55Z

Ll705: Table with some properties of piperine

[[Image:piperine.gif]]
<div align="left"><br>
== '''Properties of Piperine''' ==
</div>
{| border="1"
|+
! Property !! Value !!
|-
! Molecular Formula
| C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub> ||
|-
! Molecular Weight
|285.34 amu ||
|}

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; 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 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

It:Piperine

2006-10-19T14:03:48Z

Ll705:

[[Image:piperine.gif]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; 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 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

It:Piperine

2006-10-19T13:53:07Z

Ll705:

[[Image:piperine.gif]]

File:Piperine.gif

2006-10-19T13:50:25Z

Ll705: