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Autoxidation of fatty materials in emulsion. III. Application of GLC and TLC to studies of the histidine‐catalyzed autoxidation of methyl oleate
Author(s) -
Hampson J. W.,
Herb S. F.,
Magidman P.
Publication year - 1968
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02655504
Subject(s) - autoxidation , chemistry , histidine , catalysis , stearate , epoxide , aldehyde , emulsion , organic chemistry , enzyme
Abstract Methyl oleate, emulsified with sodium dodecyl‐sulfate, was extensively oxidized, and the amount of oleate which was reacted was determined by GLC using methyl palmitate as an internal standard. The effects of histidine, iron, and histidine plus iron were compare with the uncatalyzed reaction in the presence and absence of ultraviolet light. Results in the absence of ultraviolet light confirmed previous findings that histidine and histidine plus iron are prooxidants at the concentration studied. In the presence of ultraviolet light the rate of oleate oxidation was about 100× faster than that of the nonirradiated reaction, and the effect of the catalysts was almost negligible. The principal products, determined by GLC and TLC, were epoxide and α,β‐unsaturated carbonyl. Hydroperoxy, hydroxy, acid and aldehyde compounds were also present. Epoxy stearate, determined by GLC, compared favorably with epoxy stearate as determined by use of the Durbetaki method.