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Vaccenic acid

Vaccenic acid

IUPAC name	(E)-Octadec-11-enoic acid
Identifiers
CAS number	5281127
SMILES	CCCCCCC=CCCCCCCCCCC(=O)O
Properties
Molecular formula	C₁₈H₃₄O₂
Molar mass	282.461 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Vaccenic acid is a trans fat found in the fat of ruminants and in dairy products. Its IUPAC name is trans-7-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow).^[1]

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Vaccenic acid was discovered in 1928 in animal fats and butter. It is the main trans fatty acid isomer present in milk fat.^[1] Mammals convert it into rumenic acid, a conjugated linoleic acid,^[2]^[3] where it shows anticarcinogenic properties.^[4]

Its stereoisomer, Cis-Vaccenic acid is an Omega-7 fatty acid found in Sea Buckthorn (Hippophae rhamnoides) oil.^[5] Its IUPAC name is cis-7-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.

Old Person Smell

It has been suggested that omega-7 unsaturated fatty acids, such as palmitoleic acid and vaccenic acid, found on the skin surface may be the cause of the phenomenon commonly known as old person smell.^[6]

References

^ ^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). Retrieved on 2007-01-16.
^ Bauman, Dale. cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat. Retrieved on 2007-01-15.
^ 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. PMID 12094634. Retrieved on 2007-01-15.
^ Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C. (Oct 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. Retrieved on 2007-01-15.
^ Federal Research Centre for Nutrition and Food - Institute for Lipid Research. Seed Oil Fatty Acids Database.
^ 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.