Vaccenic acid

Vaccenic acid
IUPAC name (E)-Octadec-11-enoic acid
Identifiers
CAS number	693-72-1 Y
PubChem	5281127
ChemSpider	4444571 Y
Jmol-3D images	Image 1
SMILES CCCCCC/C=C/CCCCCCCCCC(O)=O
InChI InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+ Y Key: UWHZIFQPPBDJPM-BQYQJAHWSA-N Y InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+ Key: UWHZIFQPPBDJPM-BQYQJAHWBK
Properties
Molecular formula	C18H34O2
Molar mass	282.461 g/mol
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Vaccenic acid is an omega-7 fatty acid. It is a naturally occurring trans-fatty acid found in the fat of ruminants and in dairy products such as milk, butter, and yogurt.^[1] It is also the predominant fatty acid comprising trans fat in human milk.^[2][3]

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).^[4]

Vaccenic acid was discovered in 1928 in animal fats and butter. It is the main trans fatty acid isomer present in milk fat.^[4] Mammals convert it into rumenic acid, a conjugated linoleic acid,^[5][6] where it shows anticarcinogenic properties.^[7]

Its stereoisomer, cis-vaccenic acid, also an omega-7 fatty acid, is found in Sea Buckthorn (Hippophae rhamnoides) oil.^[8] 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 LDL cholesterol and lower triglyceride levels. The researchers are preparing to conduct further research, including human clinical trials.^[9]

Vaccenic acid is also found in human orbitofrontal cortex of patients with bipolar disorder and schizophrenia.^[10][11]

Oxidation of 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 old person smell.^[12]

References

1. ^ Natural trans fats may be good for you. May 19, 2008
2. ^ 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
3. ^ 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
4. ^ ^{a b} F. Destaillats, E. Buyukpamukcu, P.-A. Golay, F. Dionisi and F. Giuffrida (2005). "Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats". J. Dairy Sci 88 (449). 
5. ^ Bauman, Dale. "cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat". Archived from the original on 2006-09-07. http://web.archive.org/web/20060907102559/http://www.ansci.cornell.edu/bauman/human_health/index.htm. Retrieved 2007-01-15. 
6. ^ Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C (2001). "Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland". Nutr Cancer 41 (1-2): 91–7. doi:10.1207/S15327914NC41-1&2_12. PMID 12094634. 
7. ^ Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C. (October 1, 2004). "The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats". J Nutr 134 (10): 2698–704. PMID 15465769. http://jn.nutrition.org/cgi/content/abstract/134/10/2698. Retrieved 2007-01-15. 
8. ^ Federal Research Centre for Nutrition and Food - Institute for Lipid Research. "Seed Oil Fatty Acids Database". http://www.bagkf.de/sofa/. 
9. ^ AFNS. Alberta natural trans fat research earns global recognition. Apr 2, 2008.
10. ^ McNamara, RK; Jandacek, R; Rider, T; Tso, P; Hahn, CG; Richtand, NM; Stanford, KE (2007). "Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications.". Schizophr Res 91 (1-3): 37–50. doi:10.1016/j.schres.2006.11.027. PMC 1853256. PMID 17236749. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1853256. 
11. ^ McNamara, RK; Jandacek, R; Rider, T; Tso, P; Stanford, KE; Hahn, CG; Richtand, NM (2008). "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.". Psychiatry Research 160 (3): 285–299. doi:10.1016/j.psychres.2007.08.021. PMC 2620106. PMID 18715653. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2620106. 
12. ^ S. Haze, Y. Gozu, S. Nakamura, Y. Kohno, K. Sawano, H. Ohta and K. Yamazaki (2001). "2-Nonenal Newly Found in Human Body Odor Tends to Increase with Aging". Journal of Investigative Dermatology 116 (4): 520–524. doi:10.1046/j.0022-202x.2001.01287.x. PMID 11286617.