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High‐pressure liquid chromatography of autoxidized lipids: I. Methyl oleate and linoleate
Author(s) -
Neff W. E.,
Frankel E. N.,
Scholfield C. R.,
Weisleder D.
Publication year - 1978
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/bf02533711
Subject(s) - chemistry , chromatography , high performance liquid chromatography , trimethylsilyl , autoxidation , methyl oleate , ether , organic chemistry , catalysis
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.