Autoxidation products of normal and genetically modified canola oil varieties determined using liquid chromatography with mass spectrometric detection.
Normal, high stearic acid and high lauric acid canola oil varieties were heated in the presence of air to allow autoxidation to occur. After the reaction, the oils were analyzed using a non-aqueous reversed-phase high-performance liquid chromatographic separation followed by detection using atmospheric pressure chemical ionization mass spectrometry. Oxidized products were separated and identified. The major autoxidation products which remained intact were epoxides and hydroperoxides. Two classes of epoxy triacylglycerols (TAGs) were formed. One class with the epoxy group replacing a site of unsaturation and one class adjacent to a site of unsaturation, as was previously reported for model TAGs. Intact oxidation products resulted mostly from oxidation of oleic acid, while oxidation products of linoleic and linolenic acid chains decomposed to yield chain-shortened species. Both neutral and polar chain-shortened products were observed. Polar chain-shortened decomposition products eluted at very short retention times and required a different chromatographic gradient to separate the molecules. This class of molecules was tentatively identified as core aldehydes. The high stearic acid canola oil yielded more intact oxidation products containing stearic acid, as expected. The high lauric acid oil produced intact oxidation products which contained lauric acid.
Byrdwell
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WC
Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, USA. byrdwell@fau.edu
Neff
W E
WE
D002853:Chromatography, Liquid / Q000379:methods*; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry*; D005818:Genetic Engineering; D013058:Mass Spectrometry / Q000379:methods*; D010084:Oxidation-Reduction; D000074262:Rapeseed Oil
D005229:Fatty Acids, Monounsaturated; D000074262:Rapeseed Oil