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Autoxidation of Acholeplasma laidlawii membranes
Author(s) -
Wu GueyShuang,
Stein Robert A.,
Mead James F.,
McElhaney Ronald N.
Publication year - 1984
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/bf02534469
Subject(s) - autoxidation , chemistry , organic chemistry , induction period , yield (engineering) , methyl oleate , palmitic acid , linoleic acid , membrane , catalysis , biochemistry , fatty acid , materials science , metallurgy
Autoxidation of Acholeplasma laidlawii membranes (with equimolar ratio of palmitic and linoleic acid) lacks an obvious induction period, and the overall rate of disappearance of substrate does not follow closely that of typical autocatalytic kinetics. Throughout the course of autoxidation, the major oxygenated products isolated were hydroperoxides (as hydroxy esters) and compounds that gave rise to trihydroxy esters. The yield of trihydroxy esters was appreciable even at the early stage of the oxidation and eventually grew to surpass that of hydroperoxides. The positions of the three hydroxyl groups in the trihydroxy esters were determined to be mostly of the 1,2,5‐type rather than 1,2,3‐type arrangement. To a lesser extent, some degraded products, including dimethyl nonanedioate, methyl myristate, methyl pentadecanoate, methyl hexadecadienoate and methyl heptadecadienoate also were obtained. Dimethyl nonanedioate was a previously known degradation product from 9‐hydroperoxide. The shorter chain esters presumably arise from the cleavage of α‐hydroperoxides of palmitate and linoleate moieties.