View source for Vaccenic acid

{{chembox
| verifiedrevid = 299788513
|   Name = Vaccenic acid
|   ImageFile = Trans-vaccenic acid.svg
|   ImageSize = 250px
|   ImageName = Skeletal formula
|   ImageFile1 = Vaccenic-acid-3D-balls.png
|   ImageSize1 = 250px
|   ImageName1 = Ball-and-stick model
|   IUPACName = (E)-Octadec-11-enoic acid
| Section1 = {{Chembox Identifiers
|   CASNo_Ref = {{cascite}}
| CASNo = 693-72-1
|   PubChem = 5281127
|   SMILES = CCCCCC/C=C/CCCCCCCCCC(O)=O
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>18</sub>H<sub>34</sub>O<sub>2</sub>
|   MolarMass = 282.461 g/mol
|   Density = 
|   MeltingPt = 
|   BoilingPt =  
  }}
}}

'''Vaccenic acid''' is a naturally occurring [[trans fat]] found in the fat of [[ruminant]]s and in [[dairy product]]s such as [[milk]] and [[yogurt]].<ref>[http://www.latimes.com/features/health/la-he-eat19-2008may19,0,846200.story Natural trans fats may be good for you.] May 19, 2008</ref>  It is also the predominant 'trans-fat' in human milk.<ref>Precht, D and J.Molkentin C18:1, C18:2, and C8:3 trans and cis fatty acid isomers including conjugated cis delta 9, trans delta 11 linoleic acid (CLA) as well as total fat composition of German human milk lipids, Nahrung 1999 43(4) 233-244</ref><ref>Friesen, R, and S.M. Innis, Trans Fatty acids in Human milk in Canada declined with the introduction of trans fat food labeling, J. Nut 2006, 136 2558-2561</ref>

Its [[IUPAC]] name is (''E'')-11-octadecenoic acid, and its lipid shorthand name is 18:1 ''trans''-11.  The name was derived from the [[Latin]] ''vacca'' ([[cow]]).<ref name=Destaillats>{{cite journal
 |journal= J. Dairy Sci|volume=88|issue=449|year=2005
 |title=Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats
 |author=F. Destaillats, E. Buyukpamukcu, P.-A. Golay, F. Dionisi and F. Giuffrida
 |accessdate=2007-01-16}}</ref>

Vaccenic acid was discovered in [[1928]] in [[animal fat]]s and [[butter]].  It is the main ''trans'' fatty acid [[isomer]] present in [[Butterfat|milk fat]].<ref name=Destaillats/> 
Mammals convert it into [[rumenic acid]], a [[conjugated linoleic acid]],<ref name=Bauman>{{cite web
 |url =http://www.ansci.cornell.edu/bauman/human_health/index.htm
 |title=cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat
 |author = Bauman, Dale |accessdate=2007-01-15}} {{Dead link|date=October 2010|bot=H3llBot}}</ref><ref name=Banni>{{cite journal
 |author=Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C
 |title=Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland |journal=Nutr Cancer |volume=41
 |issue=1-2 |pages=91–7 |year=2001 |pmid=12094634|accessdate=2007-01-15
 |doi=10.1207/S15327914NC41-1&2_12}}</ref>
where it shows anticarcinogenic properties.<ref name=lock>{{cite journal
 |url =http://jn.nutrition.org/cgi/content/abstract/134/10/2698| journal=J Nutr|volume=134(10)|pages=2698–704
 |title=   The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats
 |author= Lock AL,  Corl BA, Barbano DM, Bauman DE,  Ip C.|accessdate=2007-01-15
 |pmid=   15465769
 |issue =10
 |date = October 1, 2004 }}</ref>

Its stereoisomer, '''cis-vaccenic acid''' is an [[Essential fatty acid#Nomenclature and terminology|omega-7 fatty acid]] found in [[Sea Buckthorn]] (''Hippophae rhamnoides'') oil.<ref name=sofa>{{cite web|url =http://www.bagkf.de/sofa/ |author= Federal Research Centre for Nutrition and Food - Institute for Lipid Research|title=Seed Oil Fatty Acids Database}}</ref>  Its [[IUPAC]] name is (''Z'')-11-octadecenoic acid, and its lipid shorthand name is 18:1 ''cis''-11.

==Health==
A 2008 study at the [[University of Alberta]] suggests that vaccenic acid feeding in rats over 16 weeks resulted in lowered total [[cholesterol]], lowered [[Low-density lipoprotein|LDL]] cholesterol and lower [[triglyceride]] levels. The researchers are preparing to conduct further research, including human clinical trials.<ref>AFNS. [http://www.ales.ualberta.ca/afns/news.cfm?story=75846 Alberta natural trans fat research earns global recognition]. Apr 2, 2008.</ref>

Vaccenic acid is also found in human [[orbitofrontal cortex]] of patients with [[bipolar disorder]] and [[schizophrenia]].<ref>{{cite journal | journal = Schizophr Res | year = 2007 | volume = 91 | issue = 1-3 | pages = 37–50 | doi = 10.1016/j.schres.2006.11.027 | pmid = 17236749 | last1 = McNamara | first1 = RK | last2 = Jandacek | first2 = R | last3 = Rider | first3 = T | last4 = Tso | first4 = P | last5 = Hahn | first5 = CG | last6 = Richtand | first6 = NM | last7 = Stanford | first7 = KE | title = Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications. | pmc = 1853256}}</ref><ref>{{cite journal | journal = Psychiatry Research | volume = 160 | year = 2008 | pages = 285–299 | doi = 10.1016/j.psychres.2007.08.021 | pmid = 18715653 | last1 = McNamara | first1 = RK | last2 = Jandacek | first2 = R | last3 = Rider | first3 = T | last4 = Tso | first4 = P | last5 = Stanford | first5 = KE | last6 = Hahn | first6 = CG | last7 = Richtand | first7 = NM | title = Deficits in docosahexaenoic acid and associated elevations in the metabolism of arachidonic acid and saturated fatty acids in the postmortem orbitofrontal cortex of patients with bipolar disorder. | issue = 3 | pmc = 2620106}}</ref>

==Old person smell==
It has been suggested that the oxidative degradation of [[Fatty acid|omega-7 unsaturated fatty acids]] on the skin surface, such as [[palmitoleic acid]] and vaccenic acid, may be the cause of the phenomenon commonly known as [[2-Nonenal|old person smell]].<ref>{{cite journal | author = S. Haze, Y. Gozu, S. Nakamura, Y. Kohno, K. Sawano, H. Ohta and K. Yamazaki | title = 2-Nonenal Newly Found in Human Body Odor Tends to Increase with Aging | year = 2001 | journal = [[Journal of Investigative Dermatology]] | volume = 116 | issue = 4 | pages = 520–524 | doi = 10.1046/j.0022-202x.2001.01287.x | pmid = 11286617}}</ref>

==References==
{{reflist}}

[[Category:Fatty acids]]
[[Category:Animal fats]]
[[Category:Dairy products]]

[[ja:バクセン酸]]
[[Category:2Fix]]