Vaccenic acid

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Vaccenic acid
Skeletal formula
Ball-and-stick model
Names
IUPAC name
(E)-Octadec-11-enoic acid
Identifiers
693-72-1 YesY
ChEBI CHEBI:28727 YesY
ChemSpider 4444571 YesY
Jmol 3D model Interactive image
PubChem 5281127
  • 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+ YesY
    Key: UWHZIFQPPBDJPM-BQYQJAHWSA-N YesY
  • 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
  • CCCCCC/C=C/CCCCCCCCCC(O)=O
Properties
C18H34O2
Molar mass 282.461 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Vaccenic acid, also known as (E)-Octadec-11-enoic acid 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, is 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. ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ AFNS. Alberta natural trans fat research earns global recognition. April 2, 2008.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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