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| Vaccenic acid | |
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| IUPAC name | (E)-Octadec-11-enoic acid |
| Identifiers | |
| CAS number | 693-72-1 |
| PubChem | |
| SMILES |
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| 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 references |
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Vaccenic acid is a naturally occurring trans fat found in the fat of ruminants and in dairy products such as milk and yogurt.1 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).2
Vaccenic acid was discovered in 1928 in animal fats and butter. It is the main trans fatty acid isomer present in milk fat.2 Mammals convert it into rumenic acid, a conjugated linoleic acid,34 where it shows anticarcinogenic properties.5
Its stereoisomer, cis-vaccenic acid is an omega-7 fatty acid found in Sea Buckthorn (Hippophae rhamnoides) oil.6 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.7
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.8
References
- ^ Natural trans fats may be good for you. May 19, 2008.
- ^ 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).
- ^ 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. doi:. PMID 12094634.
- ^ Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C. (October 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 on 15 January 2007.
- ^ Federal Research Centre for Nutrition and Food - Institute for Lipid Research. "Seed Oil Fatty Acids Database".
- ^ AFNS. Alberta natural trans fat research earns global recognition. Apr 2, 2008.
- ^ 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:.
Wikipedia content modification information:
- This page was last modified on 14 November 2008, at 03:35.
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