Vaccenic acid
Trans-unsaturated fatty acid / From Wikipedia, the free encyclopedia
Vaccenic acid is a naturally occurring trans fatty acid and an omega-7 fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt.[1][2] Trans fat in human milk may depend on trans fat content in food.[3][4]
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Preferred IUPAC name
(11E)-Octadec-11-enoic acid | |
Identifiers | |
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3D model (JSmol) |
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ChEBI | |
ChemSpider |
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ECHA InfoCard | 100.010.691 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C18H34O2 | |
Molar mass | 282.461 g/mol |
Melting point | 44 °C (111 °F) |
Boiling point | 172 °C (342 °F) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Its IUPAC name is (11E)-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. Mammals convert it into rumenic acid, a conjugated linoleic acid,[5][6] where it shows anticarcinogenic properties.[7]
Its stereoisomer, cis-vaccenic acid, is found in Sea Buckthorn (Hippophae rhamnoides) oil.[8] Its IUPAC name is (11Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.
Cows milk had highest trans-vaccenic acid content in the first few days of the cows being milked,[9] indicating that it is stockpiled similarly to omega-3 fatty acids.