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Vaccenic acid

From Wikipedia, the free encyclopedia
Trans-unsaturated fatty acid
Vaccenic acid
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
(11E)-Octadec-11-enoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.010.691Edit this at Wikidata
UNII
  • 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+ checkY
    Key: UWHZIFQPPBDJPM-BQYQJAHWSA-N checkY
  • 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 mass282.461 g/mol
Melting point44 °C (111 °F)
Boiling point172 °C (342 °F)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Vaccenic acid is a naturally occurringtrans fatty acid and anomega-7 fatty acid. It is the predominant kind of trans-fatty acid found inhuman milk, in the fat ofruminants, and indairy products such asmilk,butter, andyogurt.[1][2]Trans fat in human milk may depend on trans fat content in food.[3][4] Vaccenic acid was discovered in 1928 inanimal fats andbutter. Mammals convert it intorumenic acid, aconjugated linoleic acid,[5]

Cow milk had highest trans-vaccenic acid content in the first few days ofmilking.[6]

ItsIUPAC name is(11E)-11-octadecenoic acid, and its lipid shorthand name is18:1trans-11. The name was derived from theLatinvacca (cow).[4] Itsstereoisomer,cis-vaccenic acid, is found insea buckthorn (Hippophae rhamnoides)oil.[7] ItsIUPAC name is (11Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1cis-11.

References

[edit]
  1. ^Bowerman, Susan (May 19, 2008)."Now there are good trans fats?".Los Angeles Times.
  2. ^Precht D, Molkentin J (August 1999). "C18:1, C18:2 and C18:3 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.43 (4):233–44.doi:10.1002/(SICI)1521-3803(19990801)43:4<233::AID-FOOD233>3.0.CO;2-B.PMID 10481820.
  3. ^Friesen R, Innis SM (October 2006)."Trans fatty acids in human milk in Canada declined with the introduction of trans fat food labeling".J. Nutr.136 (10):2558–61.doi:10.1093/jn/136.10.2558.PMID 16988126.
  4. ^abDestaillats F, Buyukpamukcu E, Golay PA, Dionisi F, Giuffrida F (2005)."Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats".Journal of Dairy Science.88 (449): 449.doi:10.3168/jds.S0022-0302(05)72705-3.PMID 15653508.
  5. ^Bauman, Dale."cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat". Archived fromthe original on 2006-09-07. Retrieved2007-01-15.
  6. ^Bainbridge, Melissa L.; Cersosimo, Laura M.; Wright, André-Denis G.; Kraft, Jana (2016-03-01). Brockmann, Gudrun A. (ed.)."Content and Composition of Branched-Chain Fatty Acids in Bovine Milk Are Affected by Lactation Stage and Breed of Dairy Cow".PLOS One.11 (3) e0150386.Bibcode:2016PLoSO..1150386B.doi:10.1371/journal.pone.0150386.ISSN 1932-6203.PMC 4773160.PMID 26930646.
  7. ^Matthäus B (15 October 2012)."The New Database of Seed Oil Fatty Acids".Lipid Technology.24 (10).doi:10.1002/lite.201200227.
Saturated
ω−3 Unsaturated
ω−5 Unsaturated
ω−6 Unsaturated
ω−7 Unsaturated
ω−9 Unsaturated
ω−10 Unsaturated
ω−11 Unsaturated
ω−12 Unsaturated
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