Furan fatty acids determined as oxidation products of conjugated octadecadienoic acid.
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.
Yurawecz
M P
MP
U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition, Washington, DC 20204, USA.
Hood
J K
JK
Mossoba
M M
MM
Roach
J A
JA
Ku
Y
Y
D016588:Anticarcinogenic Agents / Q000737:chemistry; D000975:Antioxidants / Q000737:chemistry; D002849:Chromatography, Gas; D003978:Diazomethane / Q000494:pharmacology; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000737:chemistry*; D000432:Methanol; D015394:Molecular Structure; D010084:Oxidation-Reduction; D014867:Water
D016588:Anticarcinogenic Agents; D000975:Antioxidants; D005231:Fatty Acids, Unsaturated; D005663:Furans; D008041:Linoleic Acids; D014867:Water; C027369:octadecadienoic acid; D003978:Diazomethane; D019787:Linoleic Acid; D000432:Methanol