Vaccenic acid

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Vaccenic acid
Vaccenic acid'
IUPAC name (E)-Octadec-11-enoic acid
Identifiers
CAS number [693-72-1]
PubChem 5281127
SMILES CCCCCC/C=C/CCCCCCCCCC(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 (E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow).[1]

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 (Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.

[edit] 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.[6]

[edit] 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.[7]

[edit] References

  1. ^ 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). 
  2. ^ Bauman, Dale. cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat. Retrieved on 2007-01-15.
  3. ^ 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. 
  4. ^ 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. PMID 15465769. 
  5. ^ Federal Research Centre for Nutrition and Food - Institute for Lipid Research. Seed Oil Fatty Acids Database.
  6. ^ AFNS. Alberta natural trans fat research earns global recognition. Apr 2, 2008.
  7. ^ 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.