Brassidic acid: structure and properties

Chemical structure of brassidic acid

Brassidic acid (22 carbon atoms) was first prepared from erucic acid by Reimer W. in 1886.
It is a monounsaturated (one trans (E) double bond; shorthand nomenclature cannot be used to name trans fatty acids) fatty acid member of the sub-group called very long chain fatty acids (VLCFA), from 20 carbon atoms onwards, and is the trans-isomer of erucic acid.

Properties of brassidic acid

Brassidic Acid
Fig. 1 – (E)-Docos-13-enoic Acid

Molecular weight: 338.56768 g/mol
Molecular formula: C22H42O2
IUPAC name: (E)-docos-13-enoic acid
CAS registry number: 506-33-2
PubChem: 5282772

In purified form it presents as thin, crystalline plates insoluble in water, with melting point at 61-62 °C (141.8-143.6 °F; 334.15-335.15 K) and boiling point at 282 °C (539.6 °F; 555.15 K) at 30 mmHg

Other names of brassidic acid

  • (E)-13-docosenoic acid
  • trans-13-docosenoic acid
  • 13-docosenoic acid, (E)-(8CI)(9CI)
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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