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Furan fatty acids determined as oxidation products of conjugated octadecadienoic acid
Author(s) -
Yurawecz Martin P.,
Hood Jennifer K.,
Mossoba Magdi M.,
Roach John A. G.,
Ku Yuoh
Publication year - 1995
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02536995
Subject(s) - conjugated linoleic acid , chemistry , furan , methanol , conjugated system , gas chromatography , chromatography , diazomethane , fatty acid methyl ester , linoleic acid , orbitrap , organic chemistry , fatty acid , mass spectrometry , catalysis , biodiesel , polymer
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°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.