Furan fatty acids determined as oxidation products of conjugated octadecadienoic acid

Lipids. 1995 Jul;30(7):595-8. doi: 10.1007/BF02536995.

Abstract

The objective of this study was to identify oxidation products of conjugated linoleic acid (CLA), a series of octadecadienoic acids with conjugated double bonds, which have been reported to have antioxidant and anticarcinogenic properties. Reference materials of CLA were oxidized in different concentrations of water/methanol; for example, 0.5 g octadecadienoic acid was dissolved in 50 mL methanol, and 100 mL water was added; this suspension was heated at 50 degrees C and continuously aerated. Aliquots of 5 mL were taken over time, extracted with ether, treated with diazomethane and examined by gas chromatography/mass spectrometry and/or gas chromatography with flame-ionization detection. Products identified included the following furan fatty acids (FFAs): 8,11-epoxy-8,10-octadecadienoic; 9,12-epoxy-9,11-octadecadienoic; 10,13-epoxy-10,12-octadecadienoic; and 11,14-epoxy-11,13-octadecadienoic. Conjugated dienes should be considered as a possible source of FFAs, and CLA may have products common to furans in their overall oxidative scheme.

MeSH terms

  • Anticarcinogenic Agents / chemistry
  • Antioxidants / chemistry
  • Chromatography, Gas
  • Diazomethane / pharmacology
  • Fatty Acids, Unsaturated / chemistry*
  • Furans / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Linoleic Acid
  • Linoleic Acids / chemistry*
  • Methanol
  • Molecular Structure
  • Oxidation-Reduction
  • Water

Substances

  • Anticarcinogenic Agents
  • Antioxidants
  • Fatty Acids, Unsaturated
  • Furans
  • Linoleic Acids
  • Water
  • octadecadienoic acid
  • Diazomethane
  • Linoleic Acid
  • Methanol