Names | |
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Preferred IUPAC name
(11E)-Octadec-11-enoic acid | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
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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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]
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.
Two Canadian studies have shown that vaccenic acid could hold benefits over trans fats derived from vegetable shortenings, or a mixture of pork lard and soy fat, by lowering total LDL and triglyceride levels.[10][11][12][13][14] A study by the US Department of Agriculture showed that vaccenic acid raises both HDL and LDL cholesterol, whereas industrial trans fats only raise LDL with no beneficial effect on HDL.[15]
Obese rats fed a diet enriched with vaccenic acid for 16 weeks had a reduction in total cholesterol, LDL cholesterol and lower triglyceride levels,[16] with an effect comparable to CLA. This effect was not seen in lean rats.[17]
Vaccenic acid accumulates in the orbitofrontal cortex to a higher extent in patients with bipolar disorder and schizophrenia.[18][19]
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.[20]
Alkaline phosphatase was inhibited 25% by vaccenic acid in osteoblasts.[21]
A 2023 University of Chicago study found that trans-vaccenic acid enhances anti-tumor immunity by activating CD8+ T cells. This effect is accomplished by deactivating a GPR43 receptor, which activates the CREB pathway instead. The effect was produced with a diet containing 1% w/w TVA.[22]