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°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.
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Abbreviations
- CLA:
-
conjugated linoleic acid
- EI:
-
electron ionization
- F8,11 :
-
8,11-epoxy-8,10-octadecadienoic acid
- F9,12 :
-
9,12-epoxy-9,11-octadecadienoic acid
- F10,13 :
-
10,13-epoxy-10,12-octadecadienoic acid
- F11,14 :
-
11,14-epoxy-11,13-octadecadienoic acid
- FAME:
-
fatty acid methyl ester
- FFA:
-
furan fatty acid
- FID:
-
flame-ionization detection
- FT-IR:
-
Fourier transform-infrared spectroscopy
- GC/MS:
-
gas chromatography/mass spectrometry
- MI:
-
matrix isolation
- PFK:
-
perfluorokerosene
- SFC:
-
supercritical fluid chromatography
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Yurawecz, M.P., Hood, J.K., Mossoba, M.M. et al. Furan fatty acids determined as oxidation products of conjugated octadecadienoic acid. Lipids 30, 595–598 (1995). https://doi.org/10.1007/BF02536995
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DOI: https://doi.org/10.1007/BF02536995