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Autoxidized methyl oleate and linoleate were reduced with NaBH 4 and fractionated with a preparative high‐pressure liquid chromatography (HPLC) reverse phase column. Products characterized from reduced‐oxidized oleate included monohydroxy‐ and dihydroxyotadecenoates, dihydroxy‐ and epoxyoctadecanoates. Products characterized from reduced‐oxidized linoleate included hydroxy‐ cis,trans ‐ and trans,trans ‐octadecadienoates, monohydroxy‐, dihydroxy‐, trihydroxy‐, epoxyhydroxy‐, and epoxyoctadecenoates. Quantitation of oxidation products by HPLC was in agreement with gas chromatography of trimethylsilyl ether derivative. Epoxyoctadecanoate in oleate and epoxy‐ and epoxyhydroxyoctadecenoates in linoleate were the most abundant secondary oxidation products. Some mechanisms are discussed to explain formation of these secondary products.
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Neff et al. (1978) studied this question.
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