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Autoxidation of methyl linoleate initiated by the ozonide of allylbenzene
Author(s) -
Ewing James C.,
Cosgrove John P.,
Giamalva David H.,
Church Daniel F.,
Pryor William A.
Publication year - 1989
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/bf02535077
Subject(s) - autoxidation , lipidology , ozonide , chemistry , clinical chemistry , methyl oleate , organic chemistry , biochemistry , catalysis , ozonolysis
Allylbenzene ozonide (ABO), a model for polyunsaturated fatty acid (PUFA) ozonides, initiates the autoxidation of methyl linoleate (18∶2 ME) at 37°C under 760 torr of oxygen. This process is inhibited by d‐α‐tocopherol (α‐T) and 2,6‐di‐ ert ‐butyl‐4‐methylphenol (BHT). The autoxidation was followed by the appearance of conjugated diene (CD), as well as by oxygen‐uptake. The rates of autoxidation are proportional to the square root of ABO concentration, implying that the usual free radical autoxidation rate law is obeyed. Activation parameters for the thermal decomposition of ABO were determined under N 2 in the presence of radical scavengers and found to be E a =28.2 ±0.3 kcal mol −1 and log A=13.6±0.2; k d (37°C) is calculated to be (5.1±0.3)×10 −7 sec −1 . Autoxidation data are also reported for ozonides of 18∶2 ME and methyl oleate (18∶1 ME).