ChemWiki - User contributions [en]

It:Eucalyptol

2006-12-06T14:54:26Z

Ac905: /* References */

== Some Facts About Eucalyptol ==
[[Image:Eucalyptusnkoala.jpg|right]]

* Eucalyptol is a cyclic ether, which is a natural organic compound.
* It is the main component of the essential oil of some eucalyptus species (up to 90%).
* It is a colourless liquid and has a fresh camphor-like aroma and a spicy, cooling taste.
* It can be found in bay leaves, mugwort, sweet basil, wormwood, rosemary, sage and other aromatic plant foliage.
* Fractional distillation of eucalyptus oil can produce large quantities of eucalyptol with a purity of 99.6-99.8%.
* It is insoluble in water but miscible with ether, ethanol and chloroform.
[[Image:Eucalyptus.jpg |centre|300px]]

== Structure of Eucalyptol ==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

</noinclude>{| class="toccolours" border="1" style="float: left; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| <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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>
| [[Image:Eucalyptola&b.JPG|300px]]
|}

[[Image:EucalyptolIR.gif|centre|frame|Infrared Spectrum of Eucalyptol]]
[[Image:EucalyptolMS.gif|centre|frame|Mass Spectrum of Eucalyptol]]

== Synthesis of Eucalyptol ==

[[Image:Synthesisofeucalyptol.JPG]]

== Uses of Eucalyptol ==

Due to it's plesant, spicy aroma and taste, eucalyptol is a frequent ingredient of the following products:

* flavourings
* fragrances
* cosmetics
* mouthwash
* cough suppressant

It is also used in aromatherapy and dentistry.

=== Medicinal Properties of Eucalyptol ===

* Evidence has shown that eucalyptol can reduce inflammation and pain.
* It is also capable of killing leukaemia cells.
* It relaxes bronchial and vascular smooth muscle and enhances blood circulation.
* Prolonged exposure to eucalyptol (inhalation) increases cerebral blood flow.
* It is used to treat bronchitis, sinusitis and chronic rhinitis as well as asthma.
* It helps to increase penetration of medicinal drugs.
* It reduces heart rate by a parasympathetic-dependent action and induces hypotension by a direct vasorelaxation.
* It can be used as a nasal decongestant and anticough agent

== References==

http://en.wikipedia.org/wiki/Eucalyptol

http://www.chemexper.com/ (type in eucalyptol)

http://webbook.nist.gov/cgi/cbook.cgi?Name=eucalyptol&Units=SI

http://en.wikipedia.org/wiki/Eucalyptus

M.C.M.S. Soares, C.E.N. Damiani, C.M. Moreira, I. Stefanon, D.V. Vassallo; Braz J Med Biol Res, March 2005, Volume 38(3) 453-461

Adams, J., Belley, M., Tetrahedron Letters, 27 (19), 2075-2078, 1986.

It:Eucalyptol

2006-12-06T14:52:25Z

Ac905: /* Uses of Eucalyptol */

File:Synthesisofeucalyptol.JPG

2006-12-06T14:51:29Z

Ac905:

It:Eucalyptol

2006-12-06T14:50:21Z

Ac905: /* Uses of Eucalyptol */

== Some Facts About Eucalyptol ==
[[Image:Eucalyptusnkoala.jpg|right]]

* Eucalyptol is a cyclic ether, which is a natural organic compound.
* It is the main component of the essential oil of some eucalyptus species (up to 90%).
* It is a colourless liquid and has a fresh camphor-like aroma and a spicy, cooling taste.
* It can be found in bay leaves, mugwort, sweet basil, wormwood, rosemary, sage and other aromatic plant foliage.
* Fractional distillation of eucalyptus oil can produce large quantities of eucalyptol with a purity of 99.6-99.8%.
* It is insoluble in water but miscible with ether, ethanol and chloroform.
[[Image:Eucalyptus.jpg |centre|300px]]

== Structure of Eucalyptol ==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

</noinclude>{| class="toccolours" border="1" style="float: left; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| <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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>
| [[Image:Eucalyptola&b.JPG|300px]]
|}

[[Image:EucalyptolIR.gif|centre|frame|Infrared Spectrum of Eucalyptol]]
[[Image:EucalyptolMS.gif|centre|frame|Mass Spectrum of Eucalyptol]]

== Uses of Eucalyptol ==

Due to it's plesant, spicy aroma and taste, eucalyptol is a frequent ingredient of the following products:

* flavourings
* fragrances
* cosmetics
* mouthwash
* cough suppressant

It is also used in aromatherapy and dentistry.

=== Medicinal Properties of Eucalyptol ===

* Evidence has shown that eucalyptol can reduce inflammation and pain.
* It is also capable of killing leukaemia cells.
* It relaxes bronchial and vascular smooth muscle and enhances blood circulation.
* Prolonged exposure to eucalyptol (inhalation) increases cerebral blood flow.
* It is used to treat bronchitis, sinusitis and chronic rhinitis as well as asthma.
* It helps to increase penetration of medicinal drugs.
* It reduces heart rate by a parasympathetic-dependent action and induces hypotension by a direct vasorelaxation.
* It can be used as a nasal decongestant and anticough agent

== References==

http://en.wikipedia.org/wiki/Eucalyptol

http://www.chemexper.com/ (type in eucalyptol)

http://webbook.nist.gov/cgi/cbook.cgi?Name=eucalyptol&Units=SI

http://en.wikipedia.org/wiki/Eucalyptus

M.C.M.S. Soares, C.E.N. Damiani, C.M. Moreira, I. Stefanon, D.V. Vassallo; Braz J Med Biol Res, March 2005, Volume 38(3) 453-461

It:Eucalyptol

2006-12-06T14:43:48Z

Ac905: /* References */

== Some Facts About Eucalyptol ==
[[Image:Eucalyptusnkoala.jpg|right]]

* Eucalyptol is a cyclic ether, which is a natural organic compound.
* It is the main component of the essential oil of some eucalyptus species (up to 90%).
* It is a colourless liquid and has a fresh camphor-like aroma and a spicy, cooling taste.
* It can be found in bay leaves, mugwort, sweet basil, wormwood, rosemary, sage and other aromatic plant foliage.
* Fractional distillation of eucalyptus oil can produce large quantities of eucalyptol with a purity of 99.6-99.8%.
* It is insoluble in water but miscible with ether, ethanol and chloroform.
[[Image:Eucalyptus.jpg |centre|300px]]

== Structure of Eucalyptol ==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

</noinclude>{| class="toccolours" border="1" style="float: left; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| <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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>
| [[Image:Eucalyptola&b.JPG|300px]]
|}

[[Image:EucalyptolIR.gif|centre|frame|Infrared Spectrum of Eucalyptol]]
[[Image:EucalyptolMS.gif|centre|frame|Mass Spectrum of Eucalyptol]]

== Uses of Eucalyptol ==

Due to it's plesant, spicy aroma and taste, eucalyptol is a frequent ingredient of the following products:

* flavourings
* fragrances
* cosmetics
* mouthwash
* cough suppressant

Evidence has shown that eucalyptol can reduce inflammation and pain. It is also capable of killing leukaemia cells.

== References==

http://en.wikipedia.org/wiki/Eucalyptol

http://www.chemexper.com/ (type in eucalyptol)

http://webbook.nist.gov/cgi/cbook.cgi?Name=eucalyptol&Units=SI

http://en.wikipedia.org/wiki/Eucalyptus

M.C.M.S. Soares, C.E.N. Damiani, C.M. Moreira, I. Stefanon, D.V. Vassallo; Braz J Med Biol Res, March 2005, Volume 38(3) 453-461

It:Eucalyptol

2006-12-06T14:24:18Z

Ac905: /* References */

== Some Facts About Eucalyptol ==
[[Image:Eucalyptusnkoala.jpg|right]]

* Eucalyptol is a cyclic ether, which is a natural organic compound.
* It is the main component of the essential oil of some eucalyptus species (up to 90%).
* It is a colourless liquid and has a fresh camphor-like aroma and a spicy, cooling taste.
* It can be found in bay leaves, mugwort, sweet basil, wormwood, rosemary, sage and other aromatic plant foliage.
* Fractional distillation of eucalyptus oil can produce large quantities of eucalyptol with a purity of 99.6-99.8%.
* It is insoluble in water but miscible with ether, ethanol and chloroform.
[[Image:Eucalyptus.jpg |centre|300px]]

== Structure of Eucalyptol ==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

</noinclude>{| class="toccolours" border="1" style="float: left; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| <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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>
| [[Image:Eucalyptola&b.JPG|300px]]
|}

[[Image:EucalyptolIR.gif|centre|frame|Infrared Spectrum of Eucalyptol]]
[[Image:EucalyptolMS.gif|centre|frame|Mass Spectrum of Eucalyptol]]

== Uses of Eucalyptol ==

Due to it's plesant, spicy aroma and taste, eucalyptol is a frequent ingredient of the following products:

* flavourings
* fragrances
* cosmetics
* mouthwash
* cough suppressant

Evidence has shown that eucalyptol can reduce inflammation and pain. It is also capable of killing leukaemia cells.

== References==

http://en.wikipedia.org/wiki/Eucalyptol

http://www.chemexper.com/ (type in eucalyptol)

http://webbook.nist.gov/cgi/cbook.cgi?Name=eucalyptol&Units=SI

It:Eucalyptol

2006-12-06T14:22:32Z

Ac905: /* Uses of Eucalyptol */

== Some Facts About Eucalyptol ==
[[Image:Eucalyptusnkoala.jpg|right]]

* Eucalyptol is a cyclic ether, which is a natural organic compound.
* It is the main component of the essential oil of some eucalyptus species (up to 90%).
* It is a colourless liquid and has a fresh camphor-like aroma and a spicy, cooling taste.
* It can be found in bay leaves, mugwort, sweet basil, wormwood, rosemary, sage and other aromatic plant foliage.
* Fractional distillation of eucalyptus oil can produce large quantities of eucalyptol with a purity of 99.6-99.8%.
* It is insoluble in water but miscible with ether, ethanol and chloroform.
[[Image:Eucalyptus.jpg |centre|300px]]

== Structure of Eucalyptol ==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

</noinclude>{| class="toccolours" border="1" style="float: left; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| <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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>
| [[Image:Eucalyptola&b.JPG|300px]]
|}

[[Image:EucalyptolIR.gif|centre|frame|Infrared Spectrum of Eucalyptol]]
[[Image:EucalyptolMS.gif|centre|frame|Mass Spectrum of Eucalyptol]]

== Uses of Eucalyptol ==

Due to it's plesant, spicy aroma and taste, eucalyptol is a frequent ingredient of the following products:

* flavourings
* fragrances
* cosmetics
* mouthwash
* cough suppressant

Evidence has shown that eucalyptol can reduce inflammation and pain. It is also capable of killing leukaemia cells.

== References==

It:Eucalyptol

2006-12-06T14:21:14Z

Ac905: /* Structure of Eucalyptol */

== Some Facts About Eucalyptol ==
[[Image:Eucalyptusnkoala.jpg|right]]

* Eucalyptol is a cyclic ether, which is a natural organic compound.
* It is the main component of the essential oil of some eucalyptus species (up to 90%).
* It is a colourless liquid and has a fresh camphor-like aroma and a spicy, cooling taste.
* It can be found in bay leaves, mugwort, sweet basil, wormwood, rosemary, sage and other aromatic plant foliage.
* Fractional distillation of eucalyptus oil can produce large quantities of eucalyptol with a purity of 99.6-99.8%.
* It is insoluble in water but miscible with ether, ethanol and chloroform.
[[Image:Eucalyptus.jpg |centre|300px]]

== Structure of Eucalyptol ==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

</noinclude>{| class="toccolours" border="1" style="float: left; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| <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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>
| [[Image:Eucalyptola&b.JPG|300px]]
|}

[[Image:EucalyptolIR.gif|centre|frame|Infrared Spectrum of Eucalyptol]]
[[Image:EucalyptolMS.gif|centre|frame|Mass Spectrum of Eucalyptol]]

== Uses of Eucalyptol ==

Due to it's plesant, spicy aroma and taste, eucalyptol is a frequent ingredient of the following products:

* flavourings
* fragrances
* cosmetics
* mouthwash
* cough suppressant

Evidence has shown that eucalyptol can reduce inflammation and pain. It is also capable of killing leukaemia cells.

It:Eucalyptol

2006-12-06T14:16:01Z

Ac905: /* Structure of Eucalyptol */

It:Eucalyptol

2006-12-06T14:15:07Z

Ac905:

It:Eucalyptol

2006-12-06T14:08:54Z

Ac905: /* Structure of Eucalyptol */

== Some Facts About Eucalyptol ==
[[Image:Eucalyptusnkoala.jpg|right]]

* Eucalyptol is a cyclic ether, which is a natural organic compound.
* It is the main component of the essential oil of some eucalyptus species (up to 90%).
* It is a colourless liquid and has a fresh camphor-like aroma and a spicy, cooling taste.
* It can be found in bay leaves, mugwort, sweet basil, wormwood, rosemary, sage and other aromatic plant foliage.
* Fractional distillation of eucalyptus oil can produce large quantities of eucalyptol with a purity of 99.6-99.8%.
* It is insoluble in water but miscible with ether, ethanol and chloroform.
[[Image:Eucalyptus.jpg |centre|300px]]

== Structure of Eucalyptol ==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

</noinclude>{| class="toccolours" border="1" style="float: left; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| <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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>
| [[Image:Eucalyptola&b.JPG|300px]]
|}

== Infrared Spectrum of Eucalyptol (Cineol) ==

[[Image:EucalyptolIR.gif]]

File:EucalyptolMS.gif

2006-12-06T14:06:57Z

Ac905:

File:EucalyptolIR.gif

2006-12-06T14:06:36Z

Ac905:

It:Eucalyptol

2006-12-06T14:00:22Z

Ac905: /* Some Facts About Eucalyptol */

It:Eucalyptol

2006-12-06T13:40:51Z

Ac905: /* Some Facts About Eucalyptol */

File:Eucalyptus.jpg

2006-12-06T13:39:21Z

Ac905:

It:Eucalyptol

2006-12-06T13:38:47Z

Ac905: /* Some Facts About Eucalyptol */

File:Eucalyptusnkoala.jpg

2006-12-06T13:36:59Z

Ac905:

It:Eucalyptol

2006-12-06T13:36:33Z

Ac905:

== Some Facts About Eucalyptol ==

* Eucalyptol is a cyclic ether, which is a natural organic compound.
* It is the main component of the essential oil of some eucalyptus species (up to 90%).
* It is a colourless liquid and has a fresh camphor-like aroma and a spicy, cooling taste.
* It can be found in bay leaves, mugwort, sweet basil, wormwood, rosemary, sage and other aromatic plant foliage.

== Structure of Eucalyptol ==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

</noinclude>{| class="toccolours" border="1" style="float: left; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| <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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>
| [[Image:Eucalyptola&b.JPG|300px]]
|}

It:Eucalyptol

2006-12-06T13:27:35Z

Ac905: /* Structure of Eucalyptol */

== Structure of Eucalyptol ==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

</noinclude>{| class="toccolours" border="1" style="float: left; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| <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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>
| [[Image:Eucalyptola&b.JPG|300px]]
|}

It:Eucalyptol

2006-12-06T13:17:17Z

Ac905:

== Structure of Eucalyptol ==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}
[[Image:Eucalyptola&b.JPG|right|200px]]

<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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>

It:Eucalyptol

2006-12-06T13:15:39Z

Ac905: /* Structure of Eucalyptol */

</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

== Structure of Eucalyptol ==

[[Image:Eucalyptola&b.JPG|right|200px]]

<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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>

File:Eucalyptola&b.JPG

2006-12-06T13:13:58Z

Ac905:

It:Eucalyptol

2006-12-06T13:10:57Z

Ac905: /* Structure of Eucalyptol */

</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

== Structure of Eucalyptol ==

[[Image:Eucalyptol2.JPG|centre|100px]]

<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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>

It:Eucalyptol

2006-12-06T13:09:55Z

Ac905: /* Structure of Eucalyptol */

</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

== Structure of Eucalyptol ==

[[Image:Eucalyptol2.JPG|right|100px]]

<jmol>
<jmolApplet>
<size>200</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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>

It:Eucalyptol

2006-12-06T13:07:28Z

Ac905: /* Structure of Eucalyptol */

</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Eucalyptol
|-
| Synonyms
| 1,8-cineol, limonene oxide, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.
|-
| CAS No.
| 470-82-6
|-
| Molecular formula
| C<sub>10</sub>H<sub>18</sub>O
|-
| Molecular Weight
| 154.249 g/mol
|-
| Melting Point
| 1.5 °C ( 274.66 K)
|-
| Boiling Point
| 176 - 177 °C (449 - 450 K)
|-
| Density
| 0.9225 g/cm3
|-
| Refractive Index
| 1.458
|-
| Smiles
| CC12CCC(CC1)C(C)(C)O2
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2216770 MSDS]
|
|}

== Structure of Eucalyptol ==

<jmol>
<jmolApplet>
<size>200</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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>

File:Eucalyptol2.JPG

2006-12-06T12:51:30Z

Ac905:

File:Eucalyptol.JPG

2006-12-06T12:38:59Z

Ac905:

File:Eucalyptol.cdx

2006-12-06T12:33:55Z

Ac905:

It:Eucalyptol

2006-12-06T12:31:33Z

Ac905:

== Structure of Eucalyptol ==

<jmol>
<jmolApplet>
<size>200</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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>

It:Eucalyptol

2006-12-06T12:29:30Z

Ac905:

<jmol>
<jmolApplet>
<size>200</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 06-Dec-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 06-Dec-06 0 NONE 4
ATOM 1 C 0 2.391 -1.312 -0.015 0.00 0.00 C+0
ATOM 2 C 0 1.173 -0.385 -0.005 0.00 0.00 C+0
ATOM 3 C 0 1.215 0.466 1.266 0.00 0.00 C+0
ATOM 4 C 0 0.007 1.412 1.261 0.00 0.00 C+0
ATOM 5 C 0 -0.828 1.104 0.011 0.00 0.00 C+0
ATOM 6 C 0 0.006 1.437 -1.233 0.00 0.00 C+0
ATOM 7 C 0 1.231 0.515 -1.239 0.00 0.00 C+0
ATOM 8 C 0 -1.161 -0.387 -0.004 0.00 0.00 C+0
ATOM 9 C 0 -1.978 -0.728 1.243 0.00 0.00 C+0
ATOM 10 C 0 -1.999 -0.697 -1.247 0.00 0.00 C+0
ATOM 11 O 0 -0.003 -1.177 -0.035 0.00 0.00 O+0
ATOM 12 H 0 2.364 -1.957 0.863 0.00 0.00 H+0
ATOM 13 H 0 2.373 -1.924 -0.917 0.00 0.00 H+0
ATOM 14 H 0 3.302 -0.715 0.000 0.00 0.00 H+0
ATOM 15 H 0 1.170 -0.182 2.141 0.00 0.00 H+0
ATOM 16 H 0 2.136 1.049 1.286 0.00 0.00 H+0
ATOM 17 H 0 -0.593 1.247 2.156 0.00 0.00 H+0
ATOM 18 H 0 0.349 2.446 1.231 0.00 0.00 H+0
ATOM 19 H 0 -1.741 1.699 0.018 0.00 0.00 H+0
ATOM 20 H 0 -0.588 1.269 -2.131 0.00 0.00 H+0
ATOM 21 H 0 0.328 2.478 -1.193 0.00 0.00 H+0
ATOM 22 H 0 2.141 1.115 -1.213 0.00 0.00 H+0
ATOM 23 H 0 1.221 -0.099 -2.140 0.00 0.00 H+0
ATOM 24 H 0 -2.899 -0.145 1.245 0.00 0.00 H+0
ATOM 25 H 0 -2.220 -1.790 1.240 0.00 0.00 H+0
ATOM 26 H 0 -1.397 -0.490 2.134 0.00 0.00 H+0
ATOM 27 H 0 -1.432 -0.437 -2.141 0.00 0.00 H+0
ATOM 28 H 0 -2.241 -1.759 -1.266 0.00 0.00 H+0
ATOM 29 H 0 -2.920 -0.114 -1.219 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 34
CONECT 2 1 7 11 3 NONE 35
CONECT 3 2 4 15 16 NONE 36
CONECT 4 3 5 17 18 NONE 37
CONECT 5 4 6 8 19 NONE 38
CONECT 6 5 7 20 21 NONE 39
CONECT 7 6 2 22 23 NONE 40
CONECT 8 5 9 10 11 NONE 41
CONECT 9 8 24 25 26 NONE 42
CONECT 10 8 27 28 29 NONE 43
CONECT 11 8 2 0 0 NONE 44
END NONE 45
</inlineContents>
</jmolApplet>
</jmol>

It:projects

2006-12-06T12:28:52Z

Ac905: /* 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.'''''
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----
{|
|NEW: This demonstrates the use of Jmol loading discrete molecule files (rather than having to paste them into the wiki page). Upload the molecule file, and invoke it as shown here. Use it for eg loading large proteins etc. Sorry about the delay in getting this working, but the cause was pretty unobvious.--[[User:Rzepa|Rzepa]] 16:07, 4 December 2006 (UTC)
<center><jmol>
<jmolApplet>
<title>Pentahelicene</title><color>yellow</color>
<uploadedFileContents>Pentahelicene.mol</uploadedFileContents>
</jmolApplet>
<jmolMenu>
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-----
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|-
| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
| bgcolor="#CCFF00" |02
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|-
| bgcolor="#CCFF00" |18
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| bgcolor="#CCFF00" |21
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| bgcolor="#CCFF00" |22
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|bgcolor="#CCFF00" |23
| bgcolor="#CCFF00" | [[it:Vioxx|Vioxx (treatment of osteoarthritis symptoms and pain)]]
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| bgcolor="#CCFF00" |24
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| bgcolor="#CCFF00" |25
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| bgcolor="#CCFF00" |26
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| bgcolor="#CCFF00" |27
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----
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it:dichlorodifluromethane

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----
--[[User:Rzepa|Rzepa]] 12:25, 19 October 2006 (BST)--[[User:Rzepa|Rzepa]] 08:31, 5 November 2006 (UTC)

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

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[[R & S Phrases]]

It:Oxytocin

2006-11-27T16:17:35Z

Ac905:

</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Oxytocin
|-
| Synonyms
| H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2(Disulfide bond)
|-
| CAS No.
| 50-56-6
|-
| Molecular formula
| C<sub>43</sub>H<sub>66</sub>N<sub>12</sub>O<sub>12</sub>S<sub>2</sub>
|-
| Molecular Weight
| 1007.19 g/mol
|-
| Half Life
| 3 mins
|-
| Smiles
| CCC(C)C1NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(N)CSSCC(NC(=O)C(CC(=O)N)NC(=O)C(CCC(=O )N)NC1=O)C(=O)N1CCCC1C(=O)NC(CC(C)C)C(=O)NCC(=O)N
|-
| [http://www.msdsxchange.com/msdsxchange/english/show_msds.cfm?paramid1=2460210 MSDS]
|
|}

== Introduction ==

Oxytocin is a hormone found in mammals that also acts as a neurotransmitter in the brain. In females, it is released to facilitate birth after distention of the cervix and vagina during labour as well as after stimulation of the nipples during breastfeeding. In both sexes it is released during orgasm. Oxytocin in the brain is also involved in social recognition and bonding as well as the formation of trust between people.

== Discovery of oxytocin ==

Oxytocin was discovered, isolated and synthesised by Vincent du Vigneaud in 1953 along with the antideuretic hormone vasopressin. He was presented with the Nobel Prize in Chemistry in 1955.

[[Image:Vigneaud.gif ]]

== Structure of oxytocin ==

[[Image:Oxytocin3d.jpg|right]]

<jmol>
<jmolApplet>
<size>525</size>
<color>white</color>
<script>zoom 150; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
ATOM 1 C1 MOL 1 22.455 19.342 -0.112 1.00 0.00
ATOM 2 O2 MOL 1 23.402 20.100 -0.415 1.00 0.00
ATOM 3 N3 MOL 1 21.254 20.008 0.163 1.00 0.00
ATOM 4 C4 MOL 1 22.815 17.902 -0.048 1.00 0.00
ATOM 5 C5 MOL 1 19.874 19.502 0.391 1.00 0.00
ATOM 6 C6 MOL 1 21.346 21.438 0.296 1.00 0.00
ATOM 7 N7 MOL 1 21.708 17.026 0.503 1.00 0.00
ATOM 8 C8 MOL 1 23.409 17.669 -1.450 1.00 0.00
ATOM 9 C9 MOL 1 19.277 18.379 -0.581 1.00 0.00
ATOM 10 C10 MOL 1 19.168 20.869 0.276 1.00 0.00
ATOM 11 C11 MOL 1 20.064 21.773 1.036 1.00 0.00
ATOM 12 C12 MOL 1 21.549 15.563 0.566 1.00 0.00
ATOM 13 S13 MOL 1 24.786 16.540 -1.321 1.00 0.00
ATOM 14 N14 MOL 1 17.870 17.861 -0.596 1.00 0.00
ATOM 15 O15 MOL 1 20.057 17.867 -1.394 1.00 0.00
ATOM 16 O16 MOL 1 20.581 15.147 1.212 1.00 0.00
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END</inlineContents>
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Oxytocin is a peptide with nine amino acids in the following sequence:
cysteine - tyrosine - isoleucine - glutamine - asparagine - cysteine - proline - leucine - glycine
with a disulphide bridge forming between the two cysteine residues.

[[Image:Oxytocin.gif]]
[[Image:Oxytocin.JPG]]

Vasopressin has a very similar structure to oxytocin, differing by only two amino acids. The two hormones are the only ones released by the human posterior pituitary gland that do not act locally.

== Synthesis, Storage and Release of Oxytocin==

Oxytocin is made in magnocellular neurosecretory cells of the hypothalamus and by some neurons that project to other parts of the brain and spinal cord. It is then bound to neurophysin, a large peptide fragment acting as a carrier protein in the pituitary gland and stored in large vesicles before being released from the posterior lobe of the pituitary gland into the bloodstream.

[[Image:Neurophysinoxytocincomplex.jpg|frame|Oxytocin and neurophysin complex]]

When oxytocin cells in the hypothalamus generate action potentials down the axons to the nerve endings in the pituitary which contains the oxytocin vesicles, the depolarisation of the nerve endings causes secretion of oxytocin by exocytosis within the brain and a few other tissues including the ovaries and testes.
Stress can inhibit the release of oxytocin.
The production and release of oxytocin is influenced by sex steroid hormones, for example, during birth, the release of oxytocin is due to decreasing concentrations of progesterone and increasing concentrations of oestrogen.

[[Image:Synthesisofoxytocin2.GIF]]

== Functions of Oxytocin ==

=== Peripheral (hormonal) actions ===

* Stimulation of milk ejection
Oxytocin acts in the mammary glands in lactating mothers. Milk is initially secreted into small sacs within the mammary gland called alveoli. Sucking of the nipples by infants stimulates the hypothalamus and causes the neurons to fire impulses in short bursts, resulting in the secretion of oxytocin by the posterior pituitary gland. Oxytocin stimulates the contraction of myoepithelial (smooth muscle) cells which surround the mammary alveoli. The contractions lead to milk ejection for consumption.

[[Image:Myoepithelialcells.jpg|frame|Myoepithelial cells surrounding mammary alveoli]]

* Stimulation of uterine smooth muscle (myometrium) contraction at birth
During labour, cortisol, a steroid hormone, is produced by the fetus and passed into the placenta, stimulating the secretion of oestrogen and prostaglandins F2α in the placenta and inhibiting the secretion of progesterone. This leads to an increase in sensitivity of the myometrium to oxytocin, causing further contractions of the myometrium. This is in conjunction with the fact that there is an increase in oxytocin receptors in the myometrium. When the fetus stimulates the cervix and vagina, the pressure stimulates the secretion of more oxytocin which enhances contractions in order to facilitate birth.
In the first few weeks following the birth, the release of oxytocin during breastfeeding can cause painful contractions of the uterine muscle.

* Secretion into the blood at orgasm
Both males and females secrete oxytocin. In males, oxytocin is synthesised in the hypothalamus and the testes and is detected during ejaculation. It facilitates sperm transport and also affects some aspects of male sexual behaviour.

* Reduce the secretion of urine slightly
Due to its similarity to the antideuretic hormone vasopressin. A high dose of oxytocin can lead to hyponatremia, a deficiency of sodium in the blood as it can stimulate sodium excretion from the kidneys.

=== Actions in the Brain ===

Oxytocin released from the pituitary gland cannot re-enter the brain due to a blood-brain barrier. Oxytocin has a role in social behaviour in many species. The behavioural effects of oxytocin reflect the release of oxytocin from the neurons which project into the brain and spinal cord, where oxytocin receptors are present. Oxytocin released in the brain causes:
* Sexual arousal
* Bonding – concentrations of oxytocin in blood was found to be higher in people who were falling in love. A lack of oxytocin pathways in the brain is suggested to be a feature of autism.
* Establishment of maternal behaviour – during birth, an increase in the concentration of oxytocin in the cerebrospinal fluid plays a major role in ensuring that mothers become attached to their offspring and nourish them after birth. Evidence for this was obtained from experiments on other animals.
* Anti-stress functions – oxytocin reduces blood pressure and cortisol levels which reduces anxiety and fear (by inhibiting amygdala) and increases tolerance to pain. It also reduces withdrawal symptoms.
* Trust – an increase in oxytocin levels led to people displaying a higher level of trust.

== Uses of Oxytocin ==

Synthetic oxytocin is sold as a medication and can be administered by injection or as a nasal spray. The latter has better access to the brain and spinal cord and is used to stimulate breastfeeding. Synthetic oxytocin is widely used clinically to help induce and support labour and to control bleeding after delivery. In case of non-progression during birth, due to non-sufficient uterine contractions, oxytocin infused in large amounts causes further contractions of the myometrium. This must be done with care to ensure the safety of the fetus.
The nasal spray can also be used to treat those suffering from social anxieties due to the trust-inducing property in oxytocin.

== References ==
http://en.wikipedia.org/wiki/Oxytocin

http://www.vivo.colostate.edu/hbooks/pathphys/endocrine/hypopit/oxytocin.html

ColoState.edu - (from on-line textbook, Pathophysiology of the Endocrine System), R.A. Bowen

http://www.britannica.com/nobel/micro/445_91.html

http://www.rcsb.org/pdb/explore.do?structureId=1NPO

http://www.chm.bris.ac.uk/org/RJCox/4.1_Oxytocin.html

http://mammary.nih.gov/reviews/lactation/Neville002/index.html

http://www.chemexper.com/

It:Oxytocin

2006-11-27T16:14:48Z

Ac905: /* References */

</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Oxytocin
|-
| Synonyms
| H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2(Disulfide bond)
|-
| CAS No.
| 50-56-6
|-
| Molecular formula
| C<sub>43</sub>H<sub>66</sub>N<sub>12</sub>O<sub>12</sub>S<sub>2</sub>
|-
| Molecular Weight
| 1007.19 g/mol
|-
| Half Life
| 3 mins
|-
| Smiles
| CCC(C)C1NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(N)CSSCC(NC(=O)C(CC(=O)N)NC(=O)C(CCC(=O )N)NC1=O)C(=O)N1CCCC1C(=O)NC(CC(C)C)C(=O)NCC(=O)N
|-
| MSDS
|
|}

== Introduction ==

Oxytocin is a hormone found in mammals that also acts as a neurotransmitter in the brain. In females, it is released to facilitate birth after distention of the cervix and vagina during labour as well as after stimulation of the nipples during breastfeeding. In both sexes it is released during orgasm. Oxytocin in the brain is also involved in social recognition and bonding as well as the formation of trust between people.

== Discovery of oxytocin ==

Oxytocin was discovered, isolated and synthesised by Vincent du Vigneaud in 1953 along with the antideuretic hormone vasopressin. He was presented with the Nobel Prize in Chemistry in 1955.

[[Image:Vigneaud.gif ]]

== Structure of oxytocin ==

[[Image:Oxytocin3d.jpg|right]]

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ATOM 110 1H22 MOL 1 31.163 17.568 1.635 1.00 0.00
ATOM 111 3H22 MOL 1 24.654 11.521 2.661 1.00 0.00
ATOM 112 5H22 MOL 1 23.890 12.153 1.363 1.00 0.00
ATOM 113 7H22 MOL 1 32.643 17.242 -0.783 1.00 0.00
ATOM 114 9H22 MOL 1 9.700 17.641 -0.128 1.00 0.00
ATOM 115 1H23 MOL 1 10.544 16.145 -0.342 1.00 0.00
ATOM 116 3H23 MOL 1 30.072 13.796 -1.394 1.00 0.00
ATOM 117 5H23 MOL 1 33.667 17.705 1.296 1.00 0.00
ATOM 118 7H23 MOL 1 33.206 16.232 1.829 1.00 0.00
ATOM 119 9H23 MOL 1 24.161 8.715 0.114 1.00 0.00
ATOM 120 1H24 MOL 1 23.052 9.741 0.962 1.00 0.00
ATOM 121 3H24 MOL 1 30.578 11.988 0.823 1.00 0.00
ATOM 122 5H24 MOL 1 30.095 15.212 0.973 1.00 0.00
ATOM 123 7H24 MOL 1 32.415 10.964 -0.443 1.00 0.00
ATOM 124 9H24 MOL 1 32.417 12.350 -1.308 1.00 0.00
ATOM 125 1H25 MOL 1 30.418 10.168 -0.991 1.00 0.00
ATOM 126 3H25 MOL 1 30.129 11.357 -2.072 1.00 0.00
ATOM 127 5H25 MOL 1 29.024 11.016 -0.918 1.00 0.00
ATOM 128 7H25 MOL 1 34.077 14.842 -0.781 1.00 0.00
ATOM 129 9H25 MOL 1 36.052 17.419 1.804 1.00 0.00
ATOM 130 1H26 MOL 1 33.971 12.512 0.498 1.00 0.00
ATOM 131 3H26 MOL 1 32.768 12.215 1.561 1.00 0.00
ATOM 132 5H26 MOL 1 32.770 13.600 0.696 1.00 0.00
ATOM 133 7H26 MOL 1 36.248 13.884 -1.426 1.00 0.00
ATOM 134 9H26 MOL 1 38.112 16.551 1.151 1.00 0.00
ATOM 135 1H27 MOL 1 39.294 15.018 -0.088 1.00 0.00
END</inlineContents>
</jmolApplet>
</jmol>

Oxytocin is a peptide with nine amino acids in the following sequence:
cysteine - tyrosine - isoleucine - glutamine - asparagine - cysteine - proline - leucine - glycine
with a disulphide bridge forming between the two cysteine residues.

[[Image:Oxytocin.gif]]
[[Image:Oxytocin.JPG]]

Vasopressin has a very similar structure to oxytocin, differing by only two amino acids. The two hormones are the only ones released by the human posterior pituitary gland that do not act locally.

== Synthesis, Storage and Release of Oxytocin==

Oxytocin is made in magnocellular neurosecretory cells of the hypothalamus and by some neurons that project to other parts of the brain and spinal cord. It is then bound to neurophysin, a large peptide fragment acting as a carrier protein in the pituitary gland and stored in large vesicles before being released from the posterior lobe of the pituitary gland into the bloodstream.

[[Image:Neurophysinoxytocincomplex.jpg|frame|Oxytocin and neurophysin complex]]

When oxytocin cells in the hypothalamus generate action potentials down the axons to the nerve endings in the pituitary which contains the oxytocin vesicles, the depolarisation of the nerve endings causes secretion of oxytocin by exocytosis within the brain and a few other tissues including the ovaries and testes.
Stress can inhibit the release of oxytocin.
The production and release of oxytocin is influenced by sex steroid hormones, for example, during birth, the release of oxytocin is due to decreasing concentrations of progesterone and increasing concentrations of oestrogen.

[[Image:Synthesisofoxytocin2.GIF]]

== Functions of Oxytocin ==

=== Peripheral (hormonal) actions ===

* Stimulation of milk ejection
Oxytocin acts in the mammary glands in lactating mothers. Milk is initially secreted into small sacs within the mammary gland called alveoli. Sucking of the nipples by infants stimulates the hypothalamus and causes the neurons to fire impulses in short bursts, resulting in the secretion of oxytocin by the posterior pituitary gland. Oxytocin stimulates the contraction of myoepithelial (smooth muscle) cells which surround the mammary alveoli. The contractions lead to milk ejection for consumption.

[[Image:Myoepithelialcells.jpg|frame|Myoepithelial cells surrounding mammary alveoli]]

* Stimulation of uterine smooth muscle (myometrium) contraction at birth
During labour, cortisol, a steroid hormone, is produced by the fetus and passed into the placenta, stimulating the secretion of oestrogen and prostaglandins F2α in the placenta and inhibiting the secretion of progesterone. This leads to an increase in sensitivity of the myometrium to oxytocin, causing further contractions of the myometrium. This is in conjunction with the fact that there is an increase in oxytocin receptors in the myometrium. When the fetus stimulates the cervix and vagina, the pressure stimulates the secretion of more oxytocin which enhances contractions in order to facilitate birth.
In the first few weeks following the birth, the release of oxytocin during breastfeeding can cause painful contractions of the uterine muscle.

* Secretion into the blood at orgasm
Both males and females secrete oxytocin. In males, oxytocin is synthesised in the hypothalamus and the testes and is detected during ejaculation. It facilitates sperm transport and also affects some aspects of male sexual behaviour.

* Reduce the secretion of urine slightly
Due to its similarity to the antideuretic hormone vasopressin. A high dose of oxytocin can lead to hyponatremia, a deficiency of sodium in the blood as it can stimulate sodium excretion from the kidneys.

=== Actions in the Brain ===

Oxytocin released from the pituitary gland cannot re-enter the brain due to a blood-brain barrier. Oxytocin has a role in social behaviour in many species. The behavioural effects of oxytocin reflect the release of oxytocin from the neurons which project into the brain and spinal cord, where oxytocin receptors are present. Oxytocin released in the brain causes:
* Sexual arousal
* Bonding – concentrations of oxytocin in blood was found to be higher in people who were falling in love. A lack of oxytocin pathways in the brain is suggested to be a feature of autism.
* Establishment of maternal behaviour – during birth, an increase in the concentration of oxytocin in the cerebrospinal fluid plays a major role in ensuring that mothers become attached to their offspring and nourish them after birth. Evidence for this was obtained from experiments on other animals.
* Anti-stress functions – oxytocin reduces blood pressure and cortisol levels which reduces anxiety and fear (by inhibiting amygdala) and increases tolerance to pain. It also reduces withdrawal symptoms.
* Trust – an increase in oxytocin levels led to people displaying a higher level of trust.

== Uses of Oxytocin ==

Synthetic oxytocin is sold as a medication and can be administered by injection or as a nasal spray. The latter has better access to the brain and spinal cord and is used to stimulate breastfeeding. Synthetic oxytocin is widely used clinically to help induce and support labour and to control bleeding after delivery. In case of non-progression during birth, due to non-sufficient uterine contractions, oxytocin infused in large amounts causes further contractions of the myometrium. This must be done with care to ensure the safety of the fetus.
The nasal spray can also be used to treat those suffering from social anxieties due to the trust-inducing property in oxytocin.

== References ==
http://en.wikipedia.org/wiki/Oxytocin

http://www.vivo.colostate.edu/hbooks/pathphys/endocrine/hypopit/oxytocin.html

ColoState.edu - (from on-line textbook, Pathophysiology of the Endocrine System), R.A. Bowen

http://www.britannica.com/nobel/micro/445_91.html

http://www.rcsb.org/pdb/explore.do?structureId=1NPO

http://www.chm.bris.ac.uk/org/RJCox/4.1_Oxytocin.html

http://mammary.nih.gov/reviews/lactation/Neville002/index.html

http://www.chemexper.com/

It:Oxytocin

2006-11-27T16:13:14Z

Ac905: /* Structure of oxytocin */

</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Oxytocin
|-
| Synonyms
| H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2(Disulfide bond)
|-
| CAS No.
| 50-56-6
|-
| Molecular formula
| C<sub>43</sub>H<sub>66</sub>N<sub>12</sub>O<sub>12</sub>S<sub>2</sub>
|-
| Molecular Weight
| 1007.19 g/mol
|-
| Half Life
| 3 mins
|-
| Smiles
| CCC(C)C1NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(N)CSSCC(NC(=O)C(CC(=O)N)NC(=O)C(CCC(=O )N)NC1=O)C(=O)N1CCCC1C(=O)NC(CC(C)C)C(=O)NCC(=O)N
|-
| MSDS
|
|}

== Introduction ==

Oxytocin is a hormone found in mammals that also acts as a neurotransmitter in the brain. In females, it is released to facilitate birth after distention of the cervix and vagina during labour as well as after stimulation of the nipples during breastfeeding. In both sexes it is released during orgasm. Oxytocin in the brain is also involved in social recognition and bonding as well as the formation of trust between people.

== Discovery of oxytocin ==

Oxytocin was discovered, isolated and synthesised by Vincent du Vigneaud in 1953 along with the antideuretic hormone vasopressin. He was presented with the Nobel Prize in Chemistry in 1955.

[[Image:Vigneaud.gif ]]

== Structure of oxytocin ==

[[Image:Oxytocin3d.jpg|right]]

<jmol>
<jmolApplet>
<size>525</size>
<color>white</color>
<script>zoom 150; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
ATOM 1 C1 MOL 1 22.455 19.342 -0.112 1.00 0.00
ATOM 2 O2 MOL 1 23.402 20.100 -0.415 1.00 0.00
ATOM 3 N3 MOL 1 21.254 20.008 0.163 1.00 0.00
ATOM 4 C4 MOL 1 22.815 17.902 -0.048 1.00 0.00
ATOM 5 C5 MOL 1 19.874 19.502 0.391 1.00 0.00
ATOM 6 C6 MOL 1 21.346 21.438 0.296 1.00 0.00
ATOM 7 N7 MOL 1 21.708 17.026 0.503 1.00 0.00
ATOM 8 C8 MOL 1 23.409 17.669 -1.450 1.00 0.00
ATOM 9 C9 MOL 1 19.277 18.379 -0.581 1.00 0.00
ATOM 10 C10 MOL 1 19.168 20.869 0.276 1.00 0.00
ATOM 11 C11 MOL 1 20.064 21.773 1.036 1.00 0.00
ATOM 12 C12 MOL 1 21.549 15.563 0.566 1.00 0.00
ATOM 13 S13 MOL 1 24.786 16.540 -1.321 1.00 0.00
ATOM 14 N14 MOL 1 17.870 17.861 -0.596 1.00 0.00
ATOM 15 O15 MOL 1 20.057 17.867 -1.394 1.00 0.00
ATOM 16 O16 MOL 1 20.581 15.147 1.212 1.00 0.00
ATOM 17 C17 MOL 1 22.405 14.537 -0.159 1.00 0.00
ATOM 18 S18 MOL 1 26.085 17.399 0.082 1.00 0.00
ATOM 19 C19 MOL 1 16.685 18.515 -0.007 1.00 0.00
ATOM 20 C20 MOL 1 21.870 13.075 0.087 1.00 0.00
ATOM 21 N21 MOL 1 23.806 14.474 0.326 1.00 0.00
ATOM 22 C22 MOL 1 27.784 17.212 -0.467 1.00 0.00
ATOM 23 C23 MOL 1 15.508 17.514 0.081 1.00 0.00
ATOM 24 C24 MOL 1 16.392 19.807 -0.893 1.00 0.00
ATOM 25 C25 MOL 1 20.475 12.729 -0.342 1.00 0.00
ATOM 26 C26 MOL 1 24.707 13.650 -0.478 1.00 0.00
ATOM 27 C27 MOL 1 28.768 17.998 0.426 1.00 0.00
ATOM 28 N28 MOL 1 14.192 17.933 0.256 1.00 0.00
ATOM 29 O29 MOL 1 15.732 16.306 -0.051 1.00 0.00
ATOM 30 C30 MOL 1 15.543 20.997 -0.296 1.00 0.00
ATOM 31 N31 MOL 1 19.637 13.670 -1.003 1.00 0.00
ATOM 32 O32 MOL 1 20.057 11.584 -0.113 1.00 0.00
ATOM 33 O33 MOL 1 24.311 13.250 -1.580 1.00 0.00
ATOM 34 C34 MOL 1 26.036 13.141 0.025 1.00 0.00
ATOM 35 N35 MOL 1 28.429 19.422 0.321 1.00 0.00
ATOM 36 C36 MOL 1 30.113 17.774 -0.155 1.00 0.00
ATOM 37 C37 MOL 1 13.093 17.011 0.121 1.00 0.00
ATOM 38 C38 MOL 1 14.073 20.760 -0.059 1.00 0.00
ATOM 39 C39 MOL 1 15.677 22.199 -1.240 1.00 0.00
ATOM 40 C40 MOL 1 25.882 12.818 1.542 1.00 0.00
ATOM 41 N41 MOL 1 27.279 13.937 -0.322 1.00 0.00
ATOM 42 O42 MOL 1 30.263 17.836 -1.380 1.00 0.00
ATOM 43 N43 MOL 1 31.173 17.402 0.650 1.00 0.00
ATOM 44 C44 MOL 1 11.793 17.783 0.135 1.00 0.00
ATOM 45 C45 MOL 1 24.746 11.757 1.693 1.00 0.00
ATOM 46 C46 MOL 1 28.521 13.227 0.055 1.00 0.00
ATOM 47 C47 MOL 1 32.270 16.776 0.020 1.00 0.00
ATOM 48 N48 MOL 1 10.555 17.124 -0.140 1.00 0.00
ATOM 49 O49 MOL 1 11.794 18.993 0.375 1.00 0.00
ATOM 50 C50 MOL 1 25.035 10.475 0.898 1.00 0.00
ATOM 51 O51 MOL 1 28.397 12.224 0.763 1.00 0.00
ATOM 52 C52 MOL 1 29.956 13.535 -0.436 1.00 0.00
ATOM 53 C53 MOL 1 33.492 16.758 1.028 1.00 0.00
ATOM 54 C54 MOL 1 31.727 15.422 -0.451 1.00 0.00
ATOM 55 N55 MOL 1 23.977 9.551 0.632 1.00 0.00
ATOM 56 O56 MOL 1 26.166 10.242 0.451 1.00 0.00
ATOM 57 C57 MOL 1 30.682 12.103 -0.165 1.00 0.00
ATOM 58 N58 MOL 1 30.522 14.799 0.169 1.00 0.00
ATOM 59 C59 MOL 1 34.839 16.162 0.547 1.00 0.00
ATOM 60 O60 MOL 1 32.240 14.883 -1.435 1.00 0.00
ATOM 61 C61 MOL 1 32.188 11.938 -0.426 1.00 0.00
ATOM 62 C62 MOL 1 30.002 11.068 -1.123 1.00 0.00
ATOM 63 C63 MOL 1 34.915 15.190 -0.361 1.00 0.00
ATOM 64 C64 MOL 1 36.089 16.683 1.127 1.00 0.00
ATOM 65 C65 MOL 1 32.994 12.626 0.678 1.00 0.00
ATOM 66 C66 MOL 1 36.209 14.624 -0.754 1.00 0.00
ATOM 67 C67 MOL 1 37.269 16.182 0.759 1.00 0.00
ATOM 68 C68 MOL 1 37.332 15.095 -0.218 1.00 0.00
ATOM 69 O69 MOL 1 38.562 14.550 -0.583 1.00 0.00
ATOM 70 1H14 MOL 1 23.493 17.624 0.632 1.00 0.00
ATOM 71 3H14 MOL 1 19.775 18.972 1.233 1.00 0.00
ATOM 72 5H14 MOL 1 22.151 21.702 0.828 1.00 0.00
ATOM 73 7H14 MOL 1 21.376 21.884 -0.598 1.00 0.00
ATOM 74 9H14 MOL 1 20.944 17.536 0.898 1.00 0.00
ATOM 75 1H15 MOL 1 22.710 17.277 -2.049 1.00 0.00
ATOM 76 3H15 MOL 1 23.724 18.539 -1.829 1.00 0.00
ATOM 77 5H15 MOL 1 19.095 21.157 -0.679 1.00 0.00
ATOM 78 7H15 MOL 1 18.257 20.839 0.686 1.00 0.00
ATOM 79 9H15 MOL 1 20.110 21.537 2.007 1.00 0.00
ATOM 80 1H16 MOL 1 19.807 22.735 0.939 1.00 0.00
ATOM 81 3H16 MOL 1 17.719 16.983 -1.051 1.00 0.00
ATOM 82 5H16 MOL 1 22.364 14.830 -1.114 1.00 0.00
ATOM 83 7H16 MOL 1 16.834 18.808 0.937 1.00 0.00
ATOM 84 9H16 MOL 1 22.488 12.452 -0.395 1.00 0.00
ATOM 85 1H17 MOL 1 21.925 12.904 1.070 1.00 0.00
ATOM 86 3H17 MOL 1 24.112 14.961 1.144 1.00 0.00
ATOM 87 5H17 MOL 1 28.027 16.242 -0.441 1.00 0.00
ATOM 88 7H17 MOL 1 27.859 17.549 -1.406 1.00 0.00
ATOM 89 9H17 MOL 1 17.280 20.188 -1.152 1.00 0.00
ATOM 90 1H18 MOL 1 15.912 19.493 -1.713 1.00 0.00
ATOM 91 3H18 MOL 1 28.732 17.714 1.384 1.00 0.00
ATOM 92 5H18 MOL 1 14.006 18.890 0.480 1.00 0.00
ATOM 93 7H18 MOL 1 15.925 21.135 0.617 1.00 0.00
ATOM 94 9H18 MOL 1 18.711 13.410 -1.277 1.00 0.00
ATOM 95 1H19 MOL 1 19.974 14.592 -1.194 1.00 0.00
ATOM 96 3H19 MOL 1 26.238 12.312 -0.496 1.00 0.00
ATOM 97 5H19 MOL 1 29.052 19.957 0.892 1.00 0.00
ATOM 98 7H19 MOL 1 27.489 19.565 0.631 1.00 0.00
ATOM 99 9H19 MOL 1 13.178 16.514 -0.743 1.00 0.00
ATOM 100 1H20 MOL 1 13.105 16.362 0.881 1.00 0.00
ATOM 101 3H20 MOL 1 13.658 21.588 0.319 1.00 0.00
ATOM 102 5H20 MOL 1 13.956 20.005 0.587 1.00 0.00
ATOM 103 7H20 MOL 1 13.628 20.530 -0.924 1.00 0.00
ATOM 104 9H20 MOL 1 15.146 22.966 -0.880 1.00 0.00
ATOM 105 1H21 MOL 1 15.333 21.952 -2.146 1.00 0.00
ATOM 106 3H21 MOL 1 16.639 22.463 -1.309 1.00 0.00
ATOM 107 5H21 MOL 1 26.740 12.451 1.900 1.00 0.00
ATOM 108 7H21 MOL 1 25.640 13.649 2.043 1.00 0.00
ATOM 109 9H21 MOL 1 27.261 14.838 -0.755 1.00 0.00
ATOM 110 1H22 MOL 1 31.163 17.568 1.635 1.00 0.00
ATOM 111 3H22 MOL 1 24.654 11.521 2.661 1.00 0.00
ATOM 112 5H22 MOL 1 23.890 12.153 1.363 1.00 0.00
ATOM 113 7H22 MOL 1 32.643 17.242 -0.783 1.00 0.00
ATOM 114 9H22 MOL 1 9.700 17.641 -0.128 1.00 0.00
ATOM 115 1H23 MOL 1 10.544 16.145 -0.342 1.00 0.00
ATOM 116 3H23 MOL 1 30.072 13.796 -1.394 1.00 0.00
ATOM 117 5H23 MOL 1 33.667 17.705 1.296 1.00 0.00
ATOM 118 7H23 MOL 1 33.206 16.232 1.829 1.00 0.00
ATOM 119 9H23 MOL 1 24.161 8.715 0.114 1.00 0.00
ATOM 120 1H24 MOL 1 23.052 9.741 0.962 1.00 0.00
ATOM 121 3H24 MOL 1 30.578 11.988 0.823 1.00 0.00
ATOM 122 5H24 MOL 1 30.095 15.212 0.973 1.00 0.00
ATOM 123 7H24 MOL 1 32.415 10.964 -0.443 1.00 0.00
ATOM 124 9H24 MOL 1 32.417 12.350 -1.308 1.00 0.00
ATOM 125 1H25 MOL 1 30.418 10.168 -0.991 1.00 0.00
ATOM 126 3H25 MOL 1 30.129 11.357 -2.072 1.00 0.00
ATOM 127 5H25 MOL 1 29.024 11.016 -0.918 1.00 0.00
ATOM 128 7H25 MOL 1 34.077 14.842 -0.781 1.00 0.00
ATOM 129 9H25 MOL 1 36.052 17.419 1.804 1.00 0.00
ATOM 130 1H26 MOL 1 33.971 12.512 0.498 1.00 0.00
ATOM 131 3H26 MOL 1 32.768 12.215 1.561 1.00 0.00
ATOM 132 5H26 MOL 1 32.770 13.600 0.696 1.00 0.00
ATOM 133 7H26 MOL 1 36.248 13.884 -1.426 1.00 0.00
ATOM 134 9H26 MOL 1 38.112 16.551 1.151 1.00 0.00
ATOM 135 1H27 MOL 1 39.294 15.018 -0.088 1.00 0.00
END</inlineContents>
</jmolApplet>
</jmol>

Oxytocin is a peptide with nine amino acids in the following sequence:
cysteine - tyrosine - isoleucine - glutamine - asparagine - cysteine - proline - leucine - glycine
with a disulphide bridge forming between the two cysteine residues.

[[Image:Oxytocin.gif]]
[[Image:Oxytocin.JPG]]

Vasopressin has a very similar structure to oxytocin, differing by only two amino acids. The two hormones are the only ones released by the human posterior pituitary gland that do not act locally.

== Synthesis, Storage and Release of Oxytocin==

Oxytocin is made in magnocellular neurosecretory cells of the hypothalamus and by some neurons that project to other parts of the brain and spinal cord. It is then bound to neurophysin, a large peptide fragment acting as a carrier protein in the pituitary gland and stored in large vesicles before being released from the posterior lobe of the pituitary gland into the bloodstream.

[[Image:Neurophysinoxytocincomplex.jpg|frame|Oxytocin and neurophysin complex]]

When oxytocin cells in the hypothalamus generate action potentials down the axons to the nerve endings in the pituitary which contains the oxytocin vesicles, the depolarisation of the nerve endings causes secretion of oxytocin by exocytosis within the brain and a few other tissues including the ovaries and testes.
Stress can inhibit the release of oxytocin.
The production and release of oxytocin is influenced by sex steroid hormones, for example, during birth, the release of oxytocin is due to decreasing concentrations of progesterone and increasing concentrations of oestrogen.

[[Image:Synthesisofoxytocin2.GIF]]

== Functions of Oxytocin ==

=== Peripheral (hormonal) actions ===

* Stimulation of milk ejection
Oxytocin acts in the mammary glands in lactating mothers. Milk is initially secreted into small sacs within the mammary gland called alveoli. Sucking of the nipples by infants stimulates the hypothalamus and causes the neurons to fire impulses in short bursts, resulting in the secretion of oxytocin by the posterior pituitary gland. Oxytocin stimulates the contraction of myoepithelial (smooth muscle) cells which surround the mammary alveoli. The contractions lead to milk ejection for consumption.

[[Image:Myoepithelialcells.jpg|frame|Myoepithelial cells surrounding mammary alveoli]]

* Stimulation of uterine smooth muscle (myometrium) contraction at birth
During labour, cortisol, a steroid hormone, is produced by the fetus and passed into the placenta, stimulating the secretion of oestrogen and prostaglandins F2α in the placenta and inhibiting the secretion of progesterone. This leads to an increase in sensitivity of the myometrium to oxytocin, causing further contractions of the myometrium. This is in conjunction with the fact that there is an increase in oxytocin receptors in the myometrium. When the fetus stimulates the cervix and vagina, the pressure stimulates the secretion of more oxytocin which enhances contractions in order to facilitate birth.
In the first few weeks following the birth, the release of oxytocin during breastfeeding can cause painful contractions of the uterine muscle.

* Secretion into the blood at orgasm
Both males and females secrete oxytocin. In males, oxytocin is synthesised in the hypothalamus and the testes and is detected during ejaculation. It facilitates sperm transport and also affects some aspects of male sexual behaviour.

* Reduce the secretion of urine slightly
Due to its similarity to the antideuretic hormone vasopressin. A high dose of oxytocin can lead to hyponatremia, a deficiency of sodium in the blood as it can stimulate sodium excretion from the kidneys.

=== Actions in the Brain ===

Oxytocin released from the pituitary gland cannot re-enter the brain due to a blood-brain barrier. Oxytocin has a role in social behaviour in many species. The behavioural effects of oxytocin reflect the release of oxytocin from the neurons which project into the brain and spinal cord, where oxytocin receptors are present. Oxytocin released in the brain causes:
* Sexual arousal
* Bonding – concentrations of oxytocin in blood was found to be higher in people who were falling in love. A lack of oxytocin pathways in the brain is suggested to be a feature of autism.
* Establishment of maternal behaviour – during birth, an increase in the concentration of oxytocin in the cerebrospinal fluid plays a major role in ensuring that mothers become attached to their offspring and nourish them after birth. Evidence for this was obtained from experiments on other animals.
* Anti-stress functions – oxytocin reduces blood pressure and cortisol levels which reduces anxiety and fear (by inhibiting amygdala) and increases tolerance to pain. It also reduces withdrawal symptoms.
* Trust – an increase in oxytocin levels led to people displaying a higher level of trust.

== Uses of Oxytocin ==

Synthetic oxytocin is sold as a medication and can be administered by injection or as a nasal spray. The latter has better access to the brain and spinal cord and is used to stimulate breastfeeding. Synthetic oxytocin is widely used clinically to help induce and support labour and to control bleeding after delivery. In case of non-progression during birth, due to non-sufficient uterine contractions, oxytocin infused in large amounts causes further contractions of the myometrium. This must be done with care to ensure the safety of the fetus.
The nasal spray can also be used to treat those suffering from social anxieties due to the trust-inducing property in oxytocin.

== References ==
http://en.wikipedia.org/wiki/Oxytocin

http://www.vivo.colostate.edu/hbooks/pathphys/endocrine/hypopit/oxytocin.html

ColoState.edu - (from on-line textbook, Pathophysiology of the Endocrine System), R.A. Bowen

http://www.britannica.com/nobel/micro/445_91.html

http://www.rcsb.org/pdb/explore.do?structureId=1NPO

http://www.chm.bris.ac.uk/org/RJCox/4.1_Oxytocin.html

http://mammary.nih.gov/reviews/lactation/Neville002/index.html

File:Oxytocin3d.jpg

2006-11-27T16:12:08Z

Ac905:

It:Oxytocin

2006-11-27T16:09:55Z

Ac905: /* Uses of Oxytocin */

</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Oxytocin
|-
| Synonyms
| H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2(Disulfide bond)
|-
| CAS No.
| 50-56-6
|-
| Molecular formula
| C<sub>43</sub>H<sub>66</sub>N<sub>12</sub>O<sub>12</sub>S<sub>2</sub>
|-
| Molecular Weight
| 1007.19 g/mol
|-
| Half Life
| 3 mins
|-
| Smiles
| CCC(C)C1NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(N)CSSCC(NC(=O)C(CC(=O)N)NC(=O)C(CCC(=O )N)NC1=O)C(=O)N1CCCC1C(=O)NC(CC(C)C)C(=O)NCC(=O)N
|-
| MSDS
|
|}

== Introduction ==

Oxytocin is a hormone found in mammals that also acts as a neurotransmitter in the brain. In females, it is released to facilitate birth after distention of the cervix and vagina during labour as well as after stimulation of the nipples during breastfeeding. In both sexes it is released during orgasm. Oxytocin in the brain is also involved in social recognition and bonding as well as the formation of trust between people.

== Discovery of oxytocin ==

Oxytocin was discovered, isolated and synthesised by Vincent du Vigneaud in 1953 along with the antideuretic hormone vasopressin. He was presented with the Nobel Prize in Chemistry in 1955.

[[Image:Vigneaud.gif ]]

== Structure of oxytocin ==

<jmol>
<jmolApplet>
<size>525</size>
<color>white</color>
<script>zoom 150; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
ATOM 1 C1 MOL 1 22.455 19.342 -0.112 1.00 0.00
ATOM 2 O2 MOL 1 23.402 20.100 -0.415 1.00 0.00
ATOM 3 N3 MOL 1 21.254 20.008 0.163 1.00 0.00
ATOM 4 C4 MOL 1 22.815 17.902 -0.048 1.00 0.00
ATOM 5 C5 MOL 1 19.874 19.502 0.391 1.00 0.00
ATOM 6 C6 MOL 1 21.346 21.438 0.296 1.00 0.00
ATOM 7 N7 MOL 1 21.708 17.026 0.503 1.00 0.00
ATOM 8 C8 MOL 1 23.409 17.669 -1.450 1.00 0.00
ATOM 9 C9 MOL 1 19.277 18.379 -0.581 1.00 0.00
ATOM 10 C10 MOL 1 19.168 20.869 0.276 1.00 0.00
ATOM 11 C11 MOL 1 20.064 21.773 1.036 1.00 0.00
ATOM 12 C12 MOL 1 21.549 15.563 0.566 1.00 0.00
ATOM 13 S13 MOL 1 24.786 16.540 -1.321 1.00 0.00
ATOM 14 N14 MOL 1 17.870 17.861 -0.596 1.00 0.00
ATOM 15 O15 MOL 1 20.057 17.867 -1.394 1.00 0.00
ATOM 16 O16 MOL 1 20.581 15.147 1.212 1.00 0.00
ATOM 17 C17 MOL 1 22.405 14.537 -0.159 1.00 0.00
ATOM 18 S18 MOL 1 26.085 17.399 0.082 1.00 0.00
ATOM 19 C19 MOL 1 16.685 18.515 -0.007 1.00 0.00
ATOM 20 C20 MOL 1 21.870 13.075 0.087 1.00 0.00
ATOM 21 N21 MOL 1 23.806 14.474 0.326 1.00 0.00
ATOM 22 C22 MOL 1 27.784 17.212 -0.467 1.00 0.00
ATOM 23 C23 MOL 1 15.508 17.514 0.081 1.00 0.00
ATOM 24 C24 MOL 1 16.392 19.807 -0.893 1.00 0.00
ATOM 25 C25 MOL 1 20.475 12.729 -0.342 1.00 0.00
ATOM 26 C26 MOL 1 24.707 13.650 -0.478 1.00 0.00
ATOM 27 C27 MOL 1 28.768 17.998 0.426 1.00 0.00
ATOM 28 N28 MOL 1 14.192 17.933 0.256 1.00 0.00
ATOM 29 O29 MOL 1 15.732 16.306 -0.051 1.00 0.00
ATOM 30 C30 MOL 1 15.543 20.997 -0.296 1.00 0.00
ATOM 31 N31 MOL 1 19.637 13.670 -1.003 1.00 0.00
ATOM 32 O32 MOL 1 20.057 11.584 -0.113 1.00 0.00
ATOM 33 O33 MOL 1 24.311 13.250 -1.580 1.00 0.00
ATOM 34 C34 MOL 1 26.036 13.141 0.025 1.00 0.00
ATOM 35 N35 MOL 1 28.429 19.422 0.321 1.00 0.00
ATOM 36 C36 MOL 1 30.113 17.774 -0.155 1.00 0.00
ATOM 37 C37 MOL 1 13.093 17.011 0.121 1.00 0.00
ATOM 38 C38 MOL 1 14.073 20.760 -0.059 1.00 0.00
ATOM 39 C39 MOL 1 15.677 22.199 -1.240 1.00 0.00
ATOM 40 C40 MOL 1 25.882 12.818 1.542 1.00 0.00
ATOM 41 N41 MOL 1 27.279 13.937 -0.322 1.00 0.00
ATOM 42 O42 MOL 1 30.263 17.836 -1.380 1.00 0.00
ATOM 43 N43 MOL 1 31.173 17.402 0.650 1.00 0.00
ATOM 44 C44 MOL 1 11.793 17.783 0.135 1.00 0.00
ATOM 45 C45 MOL 1 24.746 11.757 1.693 1.00 0.00
ATOM 46 C46 MOL 1 28.521 13.227 0.055 1.00 0.00
ATOM 47 C47 MOL 1 32.270 16.776 0.020 1.00 0.00
ATOM 48 N48 MOL 1 10.555 17.124 -0.140 1.00 0.00
ATOM 49 O49 MOL 1 11.794 18.993 0.375 1.00 0.00
ATOM 50 C50 MOL 1 25.035 10.475 0.898 1.00 0.00
ATOM 51 O51 MOL 1 28.397 12.224 0.763 1.00 0.00
ATOM 52 C52 MOL 1 29.956 13.535 -0.436 1.00 0.00
ATOM 53 C53 MOL 1 33.492 16.758 1.028 1.00 0.00
ATOM 54 C54 MOL 1 31.727 15.422 -0.451 1.00 0.00
ATOM 55 N55 MOL 1 23.977 9.551 0.632 1.00 0.00
ATOM 56 O56 MOL 1 26.166 10.242 0.451 1.00 0.00
ATOM 57 C57 MOL 1 30.682 12.103 -0.165 1.00 0.00
ATOM 58 N58 MOL 1 30.522 14.799 0.169 1.00 0.00
ATOM 59 C59 MOL 1 34.839 16.162 0.547 1.00 0.00
ATOM 60 O60 MOL 1 32.240 14.883 -1.435 1.00 0.00
ATOM 61 C61 MOL 1 32.188 11.938 -0.426 1.00 0.00
ATOM 62 C62 MOL 1 30.002 11.068 -1.123 1.00 0.00
ATOM 63 C63 MOL 1 34.915 15.190 -0.361 1.00 0.00
ATOM 64 C64 MOL 1 36.089 16.683 1.127 1.00 0.00
ATOM 65 C65 MOL 1 32.994 12.626 0.678 1.00 0.00
ATOM 66 C66 MOL 1 36.209 14.624 -0.754 1.00 0.00
ATOM 67 C67 MOL 1 37.269 16.182 0.759 1.00 0.00
ATOM 68 C68 MOL 1 37.332 15.095 -0.218 1.00 0.00
ATOM 69 O69 MOL 1 38.562 14.550 -0.583 1.00 0.00
ATOM 70 1H14 MOL 1 23.493 17.624 0.632 1.00 0.00
ATOM 71 3H14 MOL 1 19.775 18.972 1.233 1.00 0.00
ATOM 72 5H14 MOL 1 22.151 21.702 0.828 1.00 0.00
ATOM 73 7H14 MOL 1 21.376 21.884 -0.598 1.00 0.00
ATOM 74 9H14 MOL 1 20.944 17.536 0.898 1.00 0.00
ATOM 75 1H15 MOL 1 22.710 17.277 -2.049 1.00 0.00
ATOM 76 3H15 MOL 1 23.724 18.539 -1.829 1.00 0.00
ATOM 77 5H15 MOL 1 19.095 21.157 -0.679 1.00 0.00
ATOM 78 7H15 MOL 1 18.257 20.839 0.686 1.00 0.00
ATOM 79 9H15 MOL 1 20.110 21.537 2.007 1.00 0.00
ATOM 80 1H16 MOL 1 19.807 22.735 0.939 1.00 0.00
ATOM 81 3H16 MOL 1 17.719 16.983 -1.051 1.00 0.00
ATOM 82 5H16 MOL 1 22.364 14.830 -1.114 1.00 0.00
ATOM 83 7H16 MOL 1 16.834 18.808 0.937 1.00 0.00
ATOM 84 9H16 MOL 1 22.488 12.452 -0.395 1.00 0.00
ATOM 85 1H17 MOL 1 21.925 12.904 1.070 1.00 0.00
ATOM 86 3H17 MOL 1 24.112 14.961 1.144 1.00 0.00
ATOM 87 5H17 MOL 1 28.027 16.242 -0.441 1.00 0.00
ATOM 88 7H17 MOL 1 27.859 17.549 -1.406 1.00 0.00
ATOM 89 9H17 MOL 1 17.280 20.188 -1.152 1.00 0.00
ATOM 90 1H18 MOL 1 15.912 19.493 -1.713 1.00 0.00
ATOM 91 3H18 MOL 1 28.732 17.714 1.384 1.00 0.00
ATOM 92 5H18 MOL 1 14.006 18.890 0.480 1.00 0.00
ATOM 93 7H18 MOL 1 15.925 21.135 0.617 1.00 0.00
ATOM 94 9H18 MOL 1 18.711 13.410 -1.277 1.00 0.00
ATOM 95 1H19 MOL 1 19.974 14.592 -1.194 1.00 0.00
ATOM 96 3H19 MOL 1 26.238 12.312 -0.496 1.00 0.00
ATOM 97 5H19 MOL 1 29.052 19.957 0.892 1.00 0.00
ATOM 98 7H19 MOL 1 27.489 19.565 0.631 1.00 0.00
ATOM 99 9H19 MOL 1 13.178 16.514 -0.743 1.00 0.00
ATOM 100 1H20 MOL 1 13.105 16.362 0.881 1.00 0.00
ATOM 101 3H20 MOL 1 13.658 21.588 0.319 1.00 0.00
ATOM 102 5H20 MOL 1 13.956 20.005 0.587 1.00 0.00
ATOM 103 7H20 MOL 1 13.628 20.530 -0.924 1.00 0.00
ATOM 104 9H20 MOL 1 15.146 22.966 -0.880 1.00 0.00
ATOM 105 1H21 MOL 1 15.333 21.952 -2.146 1.00 0.00
ATOM 106 3H21 MOL 1 16.639 22.463 -1.309 1.00 0.00
ATOM 107 5H21 MOL 1 26.740 12.451 1.900 1.00 0.00
ATOM 108 7H21 MOL 1 25.640 13.649 2.043 1.00 0.00
ATOM 109 9H21 MOL 1 27.261 14.838 -0.755 1.00 0.00
ATOM 110 1H22 MOL 1 31.163 17.568 1.635 1.00 0.00
ATOM 111 3H22 MOL 1 24.654 11.521 2.661 1.00 0.00
ATOM 112 5H22 MOL 1 23.890 12.153 1.363 1.00 0.00
ATOM 113 7H22 MOL 1 32.643 17.242 -0.783 1.00 0.00
ATOM 114 9H22 MOL 1 9.700 17.641 -0.128 1.00 0.00
ATOM 115 1H23 MOL 1 10.544 16.145 -0.342 1.00 0.00
ATOM 116 3H23 MOL 1 30.072 13.796 -1.394 1.00 0.00
ATOM 117 5H23 MOL 1 33.667 17.705 1.296 1.00 0.00
ATOM 118 7H23 MOL 1 33.206 16.232 1.829 1.00 0.00
ATOM 119 9H23 MOL 1 24.161 8.715 0.114 1.00 0.00
ATOM 120 1H24 MOL 1 23.052 9.741 0.962 1.00 0.00
ATOM 121 3H24 MOL 1 30.578 11.988 0.823 1.00 0.00
ATOM 122 5H24 MOL 1 30.095 15.212 0.973 1.00 0.00
ATOM 123 7H24 MOL 1 32.415 10.964 -0.443 1.00 0.00
ATOM 124 9H24 MOL 1 32.417 12.350 -1.308 1.00 0.00
ATOM 125 1H25 MOL 1 30.418 10.168 -0.991 1.00 0.00
ATOM 126 3H25 MOL 1 30.129 11.357 -2.072 1.00 0.00
ATOM 127 5H25 MOL 1 29.024 11.016 -0.918 1.00 0.00
ATOM 128 7H25 MOL 1 34.077 14.842 -0.781 1.00 0.00
ATOM 129 9H25 MOL 1 36.052 17.419 1.804 1.00 0.00
ATOM 130 1H26 MOL 1 33.971 12.512 0.498 1.00 0.00
ATOM 131 3H26 MOL 1 32.768 12.215 1.561 1.00 0.00
ATOM 132 5H26 MOL 1 32.770 13.600 0.696 1.00 0.00
ATOM 133 7H26 MOL 1 36.248 13.884 -1.426 1.00 0.00
ATOM 134 9H26 MOL 1 38.112 16.551 1.151 1.00 0.00
ATOM 135 1H27 MOL 1 39.294 15.018 -0.088 1.00 0.00
END</inlineContents>
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</jmol>

Oxytocin is a peptide with nine amino acids in the following sequence:
cysteine - tyrosine - isoleucine - glutamine - asparagine - cysteine - proline - leucine - glycine
with a disulphide bridge forming between the two cysteine residues.

[[Image:Oxytocin.gif]]
[[Image:Oxytocin.JPG]]

Vasopressin has a very similar structure to oxytocin, differing by only two amino acids. The two hormones are the only ones released by the human posterior pituitary gland that do not act locally.

== Synthesis, Storage and Release of Oxytocin==

Oxytocin is made in magnocellular neurosecretory cells of the hypothalamus and by some neurons that project to other parts of the brain and spinal cord. It is then bound to neurophysin, a large peptide fragment acting as a carrier protein in the pituitary gland and stored in large vesicles before being released from the posterior lobe of the pituitary gland into the bloodstream.

[[Image:Neurophysinoxytocincomplex.jpg|frame|Oxytocin and neurophysin complex]]

When oxytocin cells in the hypothalamus generate action potentials down the axons to the nerve endings in the pituitary which contains the oxytocin vesicles, the depolarisation of the nerve endings causes secretion of oxytocin by exocytosis within the brain and a few other tissues including the ovaries and testes.
Stress can inhibit the release of oxytocin.
The production and release of oxytocin is influenced by sex steroid hormones, for example, during birth, the release of oxytocin is due to decreasing concentrations of progesterone and increasing concentrations of oestrogen.

[[Image:Synthesisofoxytocin2.GIF]]

== Functions of Oxytocin ==

=== Peripheral (hormonal) actions ===

* Stimulation of milk ejection
Oxytocin acts in the mammary glands in lactating mothers. Milk is initially secreted into small sacs within the mammary gland called alveoli. Sucking of the nipples by infants stimulates the hypothalamus and causes the neurons to fire impulses in short bursts, resulting in the secretion of oxytocin by the posterior pituitary gland. Oxytocin stimulates the contraction of myoepithelial (smooth muscle) cells which surround the mammary alveoli. The contractions lead to milk ejection for consumption.

[[Image:Myoepithelialcells.jpg|frame|Myoepithelial cells surrounding mammary alveoli]]

* Stimulation of uterine smooth muscle (myometrium) contraction at birth
During labour, cortisol, a steroid hormone, is produced by the fetus and passed into the placenta, stimulating the secretion of oestrogen and prostaglandins F2α in the placenta and inhibiting the secretion of progesterone. This leads to an increase in sensitivity of the myometrium to oxytocin, causing further contractions of the myometrium. This is in conjunction with the fact that there is an increase in oxytocin receptors in the myometrium. When the fetus stimulates the cervix and vagina, the pressure stimulates the secretion of more oxytocin which enhances contractions in order to facilitate birth.
In the first few weeks following the birth, the release of oxytocin during breastfeeding can cause painful contractions of the uterine muscle.

* Secretion into the blood at orgasm
Both males and females secrete oxytocin. In males, oxytocin is synthesised in the hypothalamus and the testes and is detected during ejaculation. It facilitates sperm transport and also affects some aspects of male sexual behaviour.

* Reduce the secretion of urine slightly
Due to its similarity to the antideuretic hormone vasopressin. A high dose of oxytocin can lead to hyponatremia, a deficiency of sodium in the blood as it can stimulate sodium excretion from the kidneys.

=== Actions in the Brain ===

Oxytocin released from the pituitary gland cannot re-enter the brain due to a blood-brain barrier. Oxytocin has a role in social behaviour in many species. The behavioural effects of oxytocin reflect the release of oxytocin from the neurons which project into the brain and spinal cord, where oxytocin receptors are present. Oxytocin released in the brain causes:
* Sexual arousal
* Bonding – concentrations of oxytocin in blood was found to be higher in people who were falling in love. A lack of oxytocin pathways in the brain is suggested to be a feature of autism.
* Establishment of maternal behaviour – during birth, an increase in the concentration of oxytocin in the cerebrospinal fluid plays a major role in ensuring that mothers become attached to their offspring and nourish them after birth. Evidence for this was obtained from experiments on other animals.
* Anti-stress functions – oxytocin reduces blood pressure and cortisol levels which reduces anxiety and fear (by inhibiting amygdala) and increases tolerance to pain. It also reduces withdrawal symptoms.
* Trust – an increase in oxytocin levels led to people displaying a higher level of trust.

== Uses of Oxytocin ==

Synthetic oxytocin is sold as a medication and can be administered by injection or as a nasal spray. The latter has better access to the brain and spinal cord and is used to stimulate breastfeeding. Synthetic oxytocin is widely used clinically to help induce and support labour and to control bleeding after delivery. In case of non-progression during birth, due to non-sufficient uterine contractions, oxytocin infused in large amounts causes further contractions of the myometrium. This must be done with care to ensure the safety of the fetus.
The nasal spray can also be used to treat those suffering from social anxieties due to the trust-inducing property in oxytocin.

== References ==
http://en.wikipedia.org/wiki/Oxytocin

http://www.vivo.colostate.edu/hbooks/pathphys/endocrine/hypopit/oxytocin.html

ColoState.edu - (from on-line textbook, Pathophysiology of the Endocrine System), R.A. Bowen

http://www.britannica.com/nobel/micro/445_91.html

http://www.rcsb.org/pdb/explore.do?structureId=1NPO

http://www.chm.bris.ac.uk/org/RJCox/4.1_Oxytocin.html

http://mammary.nih.gov/reviews/lactation/Neville002/index.html

It:Oxytocin

2006-11-27T16:05:24Z

Ac905:

</noinclude>{| class="toccolours" border="1" style="float: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Oxytocin
|-
| Synonyms
| H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2(Disulfide bond)
|-
| CAS No.
| 50-56-6
|-
| Molecular formula
| C<sub>43</sub>H<sub>66</sub>N<sub>12</sub>O<sub>12</sub>S<sub>2</sub>
|-
| Molecular Weight
| 1007.19 g/mol
|-
| Half Life
| 3 mins
|-
| Smiles
| CCC(C)C1NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(N)CSSCC(NC(=O)C(CC(=O)N)NC(=O)C(CCC(=O )N)NC1=O)C(=O)N1CCCC1C(=O)NC(CC(C)C)C(=O)NCC(=O)N
|-
| MSDS
|
|}

== Introduction ==

Oxytocin is a hormone found in mammals that also acts as a neurotransmitter in the brain. In females, it is released to facilitate birth after distention of the cervix and vagina during labour as well as after stimulation of the nipples during breastfeeding. In both sexes it is released during orgasm. Oxytocin in the brain is also involved in social recognition and bonding as well as the formation of trust between people.

== Discovery of oxytocin ==

Oxytocin was discovered, isolated and synthesised by Vincent du Vigneaud in 1953 along with the antideuretic hormone vasopressin. He was presented with the Nobel Prize in Chemistry in 1955.

[[Image:Vigneaud.gif ]]

== Structure of oxytocin ==

<jmol>
<jmolApplet>
<size>525</size>
<color>white</color>
<script>zoom 150; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
ATOM 1 C1 MOL 1 22.455 19.342 -0.112 1.00 0.00
ATOM 2 O2 MOL 1 23.402 20.100 -0.415 1.00 0.00
ATOM 3 N3 MOL 1 21.254 20.008 0.163 1.00 0.00
ATOM 4 C4 MOL 1 22.815 17.902 -0.048 1.00 0.00
ATOM 5 C5 MOL 1 19.874 19.502 0.391 1.00 0.00
ATOM 6 C6 MOL 1 21.346 21.438 0.296 1.00 0.00
ATOM 7 N7 MOL 1 21.708 17.026 0.503 1.00 0.00
ATOM 8 C8 MOL 1 23.409 17.669 -1.450 1.00 0.00
ATOM 9 C9 MOL 1 19.277 18.379 -0.581 1.00 0.00
ATOM 10 C10 MOL 1 19.168 20.869 0.276 1.00 0.00
ATOM 11 C11 MOL 1 20.064 21.773 1.036 1.00 0.00
ATOM 12 C12 MOL 1 21.549 15.563 0.566 1.00 0.00
ATOM 13 S13 MOL 1 24.786 16.540 -1.321 1.00 0.00
ATOM 14 N14 MOL 1 17.870 17.861 -0.596 1.00 0.00
ATOM 15 O15 MOL 1 20.057 17.867 -1.394 1.00 0.00
ATOM 16 O16 MOL 1 20.581 15.147 1.212 1.00 0.00
ATOM 17 C17 MOL 1 22.405 14.537 -0.159 1.00 0.00
ATOM 18 S18 MOL 1 26.085 17.399 0.082 1.00 0.00
ATOM 19 C19 MOL 1 16.685 18.515 -0.007 1.00 0.00
ATOM 20 C20 MOL 1 21.870 13.075 0.087 1.00 0.00
ATOM 21 N21 MOL 1 23.806 14.474 0.326 1.00 0.00
ATOM 22 C22 MOL 1 27.784 17.212 -0.467 1.00 0.00
ATOM 23 C23 MOL 1 15.508 17.514 0.081 1.00 0.00
ATOM 24 C24 MOL 1 16.392 19.807 -0.893 1.00 0.00
ATOM 25 C25 MOL 1 20.475 12.729 -0.342 1.00 0.00
ATOM 26 C26 MOL 1 24.707 13.650 -0.478 1.00 0.00
ATOM 27 C27 MOL 1 28.768 17.998 0.426 1.00 0.00
ATOM 28 N28 MOL 1 14.192 17.933 0.256 1.00 0.00
ATOM 29 O29 MOL 1 15.732 16.306 -0.051 1.00 0.00
ATOM 30 C30 MOL 1 15.543 20.997 -0.296 1.00 0.00
ATOM 31 N31 MOL 1 19.637 13.670 -1.003 1.00 0.00
ATOM 32 O32 MOL 1 20.057 11.584 -0.113 1.00 0.00
ATOM 33 O33 MOL 1 24.311 13.250 -1.580 1.00 0.00
ATOM 34 C34 MOL 1 26.036 13.141 0.025 1.00 0.00
ATOM 35 N35 MOL 1 28.429 19.422 0.321 1.00 0.00
ATOM 36 C36 MOL 1 30.113 17.774 -0.155 1.00 0.00
ATOM 37 C37 MOL 1 13.093 17.011 0.121 1.00 0.00
ATOM 38 C38 MOL 1 14.073 20.760 -0.059 1.00 0.00
ATOM 39 C39 MOL 1 15.677 22.199 -1.240 1.00 0.00
ATOM 40 C40 MOL 1 25.882 12.818 1.542 1.00 0.00
ATOM 41 N41 MOL 1 27.279 13.937 -0.322 1.00 0.00
ATOM 42 O42 MOL 1 30.263 17.836 -1.380 1.00 0.00
ATOM 43 N43 MOL 1 31.173 17.402 0.650 1.00 0.00
ATOM 44 C44 MOL 1 11.793 17.783 0.135 1.00 0.00
ATOM 45 C45 MOL 1 24.746 11.757 1.693 1.00 0.00
ATOM 46 C46 MOL 1 28.521 13.227 0.055 1.00 0.00
ATOM 47 C47 MOL 1 32.270 16.776 0.020 1.00 0.00
ATOM 48 N48 MOL 1 10.555 17.124 -0.140 1.00 0.00
ATOM 49 O49 MOL 1 11.794 18.993 0.375 1.00 0.00
ATOM 50 C50 MOL 1 25.035 10.475 0.898 1.00 0.00
ATOM 51 O51 MOL 1 28.397 12.224 0.763 1.00 0.00
ATOM 52 C52 MOL 1 29.956 13.535 -0.436 1.00 0.00
ATOM 53 C53 MOL 1 33.492 16.758 1.028 1.00 0.00
ATOM 54 C54 MOL 1 31.727 15.422 -0.451 1.00 0.00
ATOM 55 N55 MOL 1 23.977 9.551 0.632 1.00 0.00
ATOM 56 O56 MOL 1 26.166 10.242 0.451 1.00 0.00
ATOM 57 C57 MOL 1 30.682 12.103 -0.165 1.00 0.00
ATOM 58 N58 MOL 1 30.522 14.799 0.169 1.00 0.00
ATOM 59 C59 MOL 1 34.839 16.162 0.547 1.00 0.00
ATOM 60 O60 MOL 1 32.240 14.883 -1.435 1.00 0.00
ATOM 61 C61 MOL 1 32.188 11.938 -0.426 1.00 0.00
ATOM 62 C62 MOL 1 30.002 11.068 -1.123 1.00 0.00
ATOM 63 C63 MOL 1 34.915 15.190 -0.361 1.00 0.00
ATOM 64 C64 MOL 1 36.089 16.683 1.127 1.00 0.00
ATOM 65 C65 MOL 1 32.994 12.626 0.678 1.00 0.00
ATOM 66 C66 MOL 1 36.209 14.624 -0.754 1.00 0.00
ATOM 67 C67 MOL 1 37.269 16.182 0.759 1.00 0.00
ATOM 68 C68 MOL 1 37.332 15.095 -0.218 1.00 0.00
ATOM 69 O69 MOL 1 38.562 14.550 -0.583 1.00 0.00
ATOM 70 1H14 MOL 1 23.493 17.624 0.632 1.00 0.00
ATOM 71 3H14 MOL 1 19.775 18.972 1.233 1.00 0.00
ATOM 72 5H14 MOL 1 22.151 21.702 0.828 1.00 0.00
ATOM 73 7H14 MOL 1 21.376 21.884 -0.598 1.00 0.00
ATOM 74 9H14 MOL 1 20.944 17.536 0.898 1.00 0.00
ATOM 75 1H15 MOL 1 22.710 17.277 -2.049 1.00 0.00
ATOM 76 3H15 MOL 1 23.724 18.539 -1.829 1.00 0.00
ATOM 77 5H15 MOL 1 19.095 21.157 -0.679 1.00 0.00
ATOM 78 7H15 MOL 1 18.257 20.839 0.686 1.00 0.00
ATOM 79 9H15 MOL 1 20.110 21.537 2.007 1.00 0.00
ATOM 80 1H16 MOL 1 19.807 22.735 0.939 1.00 0.00
ATOM 81 3H16 MOL 1 17.719 16.983 -1.051 1.00 0.00
ATOM 82 5H16 MOL 1 22.364 14.830 -1.114 1.00 0.00
ATOM 83 7H16 MOL 1 16.834 18.808 0.937 1.00 0.00
ATOM 84 9H16 MOL 1 22.488 12.452 -0.395 1.00 0.00
ATOM 85 1H17 MOL 1 21.925 12.904 1.070 1.00 0.00
ATOM 86 3H17 MOL 1 24.112 14.961 1.144 1.00 0.00
ATOM 87 5H17 MOL 1 28.027 16.242 -0.441 1.00 0.00
ATOM 88 7H17 MOL 1 27.859 17.549 -1.406 1.00 0.00
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ATOM 90 1H18 MOL 1 15.912 19.493 -1.713 1.00 0.00
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Oxytocin is a peptide with nine amino acids in the following sequence:
cysteine - tyrosine - isoleucine - glutamine - asparagine - cysteine - proline - leucine - glycine
with a disulphide bridge forming between the two cysteine residues.

[[Image:Oxytocin.gif]]
[[Image:Oxytocin.JPG]]

Vasopressin has a very similar structure to oxytocin, differing by only two amino acids. The two hormones are the only ones released by the human posterior pituitary gland that do not act locally.

== Synthesis, Storage and Release of Oxytocin==

Oxytocin is made in magnocellular neurosecretory cells of the hypothalamus and by some neurons that project to other parts of the brain and spinal cord. It is then bound to neurophysin, a large peptide fragment acting as a carrier protein in the pituitary gland and stored in large vesicles before being released from the posterior lobe of the pituitary gland into the bloodstream.

[[Image:Neurophysinoxytocincomplex.jpg|frame|Oxytocin and neurophysin complex]]

When oxytocin cells in the hypothalamus generate action potentials down the axons to the nerve endings in the pituitary which contains the oxytocin vesicles, the depolarisation of the nerve endings causes secretion of oxytocin by exocytosis within the brain and a few other tissues including the ovaries and testes.
Stress can inhibit the release of oxytocin.
The production and release of oxytocin is influenced by sex steroid hormones, for example, during birth, the release of oxytocin is due to decreasing concentrations of progesterone and increasing concentrations of oestrogen.

[[Image:Synthesisofoxytocin2.GIF]]

== Functions of Oxytocin ==

=== Peripheral (hormonal) actions ===

* Stimulation of milk ejection
Oxytocin acts in the mammary glands in lactating mothers. Milk is initially secreted into small sacs within the mammary gland called alveoli. Sucking of the nipples by infants stimulates the hypothalamus and causes the neurons to fire impulses in short bursts, resulting in the secretion of oxytocin by the posterior pituitary gland. Oxytocin stimulates the contraction of myoepithelial (smooth muscle) cells which surround the mammary alveoli. The contractions lead to milk ejection for consumption.

[[Image:Myoepithelialcells.jpg|frame|Myoepithelial cells surrounding mammary alveoli]]

* Stimulation of uterine smooth muscle (myometrium) contraction at birth
During labour, cortisol, a steroid hormone, is produced by the fetus and passed into the placenta, stimulating the secretion of oestrogen and prostaglandins F2α in the placenta and inhibiting the secretion of progesterone. This leads to an increase in sensitivity of the myometrium to oxytocin, causing further contractions of the myometrium. This is in conjunction with the fact that there is an increase in oxytocin receptors in the myometrium. When the fetus stimulates the cervix and vagina, the pressure stimulates the secretion of more oxytocin which enhances contractions in order to facilitate birth.
In the first few weeks following the birth, the release of oxytocin during breastfeeding can cause painful contractions of the uterine muscle.

* Secretion into the blood at orgasm
Both males and females secrete oxytocin. In males, oxytocin is synthesised in the hypothalamus and the testes and is detected during ejaculation. It facilitates sperm transport and also affects some aspects of male sexual behaviour.

* Reduce the secretion of urine slightly
Due to its similarity to the antideuretic hormone vasopressin. A high dose of oxytocin can lead to hyponatremia, a deficiency of sodium in the blood as it can stimulate sodium excretion from the kidneys.

=== Actions in the Brain ===

Oxytocin released from the pituitary gland cannot re-enter the brain due to a blood-brain barrier. Oxytocin has a role in social behaviour in many species. The behavioural effects of oxytocin reflect the release of oxytocin from the neurons which project into the brain and spinal cord, where oxytocin receptors are present. Oxytocin released in the brain causes:
* Sexual arousal
* Bonding – concentrations of oxytocin in blood was found to be higher in people who were falling in love. A lack of oxytocin pathways in the brain is suggested to be a feature of autism.
* Establishment of maternal behaviour – during birth, an increase in the concentration of oxytocin in the cerebrospinal fluid plays a major role in ensuring that mothers become attached to their offspring and nourish them after birth. Evidence for this was obtained from experiments on other animals.
* Anti-stress functions – oxytocin reduces blood pressure and cortisol levels which reduces anxiety and fear (by inhibiting amygdala) and increases tolerance to pain. It also reduces withdrawal symptoms.
* Trust – an increase in oxytocin levels led to people displaying a higher level of trust.

== Uses of Oxytocin ==

Synthetic oxytocin is sold as a medication and can be administered by injection or as a nasal spray. The latter has better access to the brain and spinal cord and is used to stimulate breastfeeding. Synthetic oxytocin is widely used clinically to help induce and support labour and to control bleeding after delivery. In case of non-progression during birth, due to non-sufficient uterine contractions, oxytocin infused in large amounts causes further contractions of the myometrium. This must be done with care to ensure the safety of the fetus.
The nasal spray can also be used to treat those suffering from social anxieties due to the trust-inducing property in oxytocin.

It:Oxytocin

2006-11-27T15:46:07Z

Ac905: /* Peripheral (hormonal) actions */

== Introduction ==

Oxytocin is a hormone found in mammals that also acts as a neurotransmitter in the brain. In females, it is released to facilitate birth after distention of the cervix and vagina during labour as well as after stimulation of the nipples during breastfeeding. In both sexes it is released during orgasm. Oxytocin in the brain is also involved in social recognition and bonding as well as the formation of trust between people.

== Discovery of oxytocin ==

Oxytocin was discovered, isolated and synthesised by Vincent du Vigneaud in 1953 along with the antideuretic hormone vasopressin. He was presented with the Nobel Prize in Chemistry in 1955.

[[Image:Vigneaud.gif ]]

== Structure of oxytocin ==

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Oxytocin is a peptide with nine amino acids in the following sequence:
cysteine - tyrosine - isoleucine - glutamine - asparagine - cysteine - proline - leucine - glycine
with a disulphide bridge forming between the two cysteine residues.

[[Image:Oxytocin.gif]]
[[Image:Oxytocin.JPG]]

Vasopressin has a very similar structure to oxytocin, differing by only two amino acids. The two hormones are the only ones released by the human posterior pituitary gland that do not act locally.

== Synthesis, Storage and Release of Oxytocin==

Oxytocin is made in magnocellular neurosecretory cells of the hypothalamus and by some neurons that project to other parts of the brain and spinal cord. It is then bound to neurophysin, a large peptide fragment acting as a carrier protein in the pituitary gland and stored in large vesicles before being released from the posterior lobe of the pituitary gland into the bloodstream.

[[Image:Neurophysinoxytocincomplex.jpg|frame|Oxytocin and neurophysin complex]]

When oxytocin cells in the hypothalamus generate action potentials down the axons to the nerve endings in the pituitary which contains the oxytocin vesicles, the depolarisation of the nerve endings causes secretion of oxytocin by exocytosis within the brain and a few other tissues including the ovaries and testes.
Stress can inhibit the release of oxytocin.
The production and release of oxytocin is influenced by sex steroid hormones, for example, during birth, the release of oxytocin is due to decreasing concentrations of progesterone and increasing concentrations of oestrogen.

[[Image:Synthesisofoxytocin2.GIF]]

== Functions of Oxytocin ==

=== Peripheral (hormonal) actions ===

* Stimulation of milk ejection
Oxytocin acts in the mammary glands in lactating mothers. Milk is initially secreted into small sacs within the mammary gland called alveoli. Sucking of the nipples by infants stimulates the hypothalamus and causes the neurons to fire impulses in short bursts, resulting in the secretion of oxytocin by the posterior pituitary gland. Oxytocin stimulates the contraction of myoepithelial (smooth muscle) cells which surround the mammary alveoli. The contractions lead to milk ejection for consumption.

[[Image:Myoepithelialcells.jpg|frame|Myoepithelial cells surrounding mammary alveoli]]

* Stimulation of uterine smooth muscle (myometrium) contraction at birth
During labour, cortisol, a steroid hormone, is produced by the fetus and passed into the placenta, stimulating the secretion of oestrogen and prostaglandins F2α in the placenta and inhibiting the secretion of progesterone. This leads to an increase in sensitivity of the myometrium to oxytocin, causing further contractions of the myometrium. This is in conjunction with the fact that there is an increase in oxytocin receptors in the myometrium. When the fetus stimulates the cervix and vagina, the pressure stimulates the secretion of more oxytocin which enhances contractions in order to facilitate birth.
In the first few weeks following the birth, the release of oxytocin during breastfeeding can cause painful contractions of the uterine muscle.

* Secretion into the blood at orgasm
Both males and females secrete oxytocin. In males, oxytocin is synthesised in the hypothalamus and the testes and is detected during ejaculation. It facilitates sperm transport and also affects some aspects of male sexual behaviour.

* Reduce the secretion of urine slightly
Due to its similarity to the antideuretic hormone vasopressin. A high dose of oxytocin can lead to hyponatremia, a deficiency of sodium in the blood as it can stimulate sodium excretion from the kidneys.

=== Actions in the Brain ===

Oxytocin released from the pituitary gland cannot re-enter the brain due to a blood-brain barrier. Oxytocin has a role in social behaviour in many species. The behavioural effects of oxytocin reflect the release of oxytocin from the neurons which project into the brain and spinal cord, where oxytocin receptors are present. Oxytocin released in the brain causes:
* Sexual arousal
* Bonding – concentrations of oxytocin in blood was found to be higher in people who were falling in love. A lack of oxytocin pathways in the brain is suggested to be a feature of autism.
* Establishment of maternal behaviour – during birth, an increase in the concentration of oxytocin in the cerebrospinal fluid plays a major role in ensuring that mothers become attached to their offspring and nourish them after birth. Evidence for this was obtained from experiments on other animals.
* Anti-stress functions – oxytocin reduces blood pressure and cortisol levels which reduces anxiety and fear (by inhibiting amygdala) and increases tolerance to pain. It also reduces withdrawal symptoms.
* Trust – an increase in oxytocin levels led to people displaying a higher level of trust.

== Uses of Oxytocin ==

Synthetic oxytocin is sold as a medication and can be administered by injection or as a nasal spray. The latter has better access to the brain and spinal cord and is used to stimulate breastfeeding. Synthetic oxytocin is widely used clinically to help induce and support labour and to control bleeding after delivery. In case of non-progression during birth, due to non-sufficient uterine contractions, oxytocin infused in large amounts causes further contractions of the myometrium. This must be done with care to ensure the safety of the fetus.
The nasal spray can also be used to treat those suffering from social anxieties due to the trust-inducing property in oxytocin.

File:Myoepithelialcells.jpg

2006-11-27T15:40:32Z

Ac905:

It:Oxytocin

2006-11-27T15:40:07Z

Ac905: /* Synthesis, Storage and Release of Oxytocin */

It:Oxytocin

2006-11-27T15:35:49Z

Ac905: /* Synthesis, Storage and Release of Oxytocin */

File:Synthesisofoxytocin2.GIF

2006-11-27T15:34:14Z

Ac905:

It:Oxytocin

2006-11-27T15:32:11Z

Ac905: /* Synthesis, Storage and Release of Oxytocin */

It:Oxytocin

2006-11-27T15:27:01Z

Ac905: /* Synthesis, Storage and Release of Oxytocin */

It:Oxytocin

2006-11-27T15:24:13Z

Ac905: /* Synthesis, Storage and Release of Oxytocin */

File:Neurophysinoxytocincomplex.jpg

2006-11-27T15:21:09Z

Ac905:

It:Oxytocin

2006-11-27T15:14:28Z

Ac905: /* Structure of oxytocin */

It:Oxytocin

2006-11-27T15:12:24Z

Ac905: /* Structure of oxytocin */

File:Oxytocin.JPG

2006-11-27T15:09:33Z

Ac905: