Vaccenic acid: structure, properties, and food sources

Chemical structure of vaccenic acid

Vaccenic acid (18 carbon atoms), from the Latin word vacca, meaning cow, was discovered by Bertram S.H. in 1928 and was the first demonstration of presence of “trans” isomers of fatty acids in ruminant fats.
It is a monounsaturated fatty acid (one trans double bond; shorthand nomenclature cannot be used to name trans fatty acids)  member of the sub-group called long chain fatty acids (LCFA) (from 14 to 18 carbon atoms).

Properties of vaccenic acid

Vaccenic Acid
Fig. 1 – (E)-octadec-11-enoic Acid

Molecular weight: 282.46136 g/mol
Molecular formula: C18H34O2
IUPAC name: (E)-octadec-11-enoic acid
CAS registry number: 693-72-1
PubChem: 5281127

In purified form its melting point is at 44 °C (111.2 °F; 317.15 K).

Other names of vaccenic acid

  • trans-vaccenic acid
  • trans-11-octadecenoic acid
  • (11E)-octadecenoic acid
  • (E)-11-octadecenoic acid
  • (11E)-octadec-11-enoic acid

Sources of vaccenic acid

It is the major trans fatty acid, present as glycerol ester, in ruminant fats, like ox and sheep fats, and in fats of dairy products.
It results from the bacterial hydrogenation of rumenic acid in the first stomach of ruminants. However, it is present in small proportion.

References

Akoh C.C. and Min D.B. “Food lipids: chemistry, nutrition, and biotechnology” 3th ed. 2008

Chow Ching K. “Fatty acids in foods and their health implication” 3th ed. 2008


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