Oxidation of lipids: III. Oxidation of methyl linoleate in solution
- 1 December 1982
- Vol. 17 (12), 870-877
- https://doi.org/10.1007/bf02534581
Abstract
The effects of oxygen pressure, substrate concentration and solvent on the rate and products of oxidation of methyl linoleate were studied at 50 C with azobisisobutyronitrile as a radical initiator. The absolute and quantitative numbers for oxygen uptake, substrate disappearance, and formation of conjugated diene and hydroperoxides were measured. Under the present conditions, 4 conjugated diene hydroperoxides, 13-hydroperoxy-9-cis, 11-trans-(2a), 13-hydroperoxy-9-trans, 11-trans-(3a), 9-hydroperoxy-10-trans, 12-cis-(4a), and 9-hydroperoxy-10-trans, 12-trans-(5a) octadecadienoic acid methyl esters, were formed almost quantitatively. The rate of oxidation decreased with decreasing oxygen pressure. However, the ratio ofcis,trans totrans,trans hydroperoxides, (2a+4a)/(3a+5a), was independent of oxygen pressure, and this ratio increased with increasing methyl linoleate concentration, as found recently by Porter. Further, the rate of oxidation and the ratio ofcis,trans/trans,trans hydroperoxides were dependent on solvent and increased with an increase in dielectric constant of solvent. A mechanism of methyl linoleate oxidation consistent with these results is discussed.This publication has 23 references indexed in Scilit:
- Oxidation of Lipids. I. Quantitative Determination of the Oxidation of Methyl Linoleate and Methyl LinolenateBulletin of the Chemical Society of Japan, 1982
- Autoxidation of biological molecules. 1. Antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitroJournal of the American Chemical Society, 1981
- The mechanism of the rearrangement of linoleate hydroperoxidesChemistry and Physics of Lipids, 1979
- Thermal isomerisation of methyl linoleate hydroperoxides. Evidence of molecular oxygen as a leaving group in a radical rearrangementJournal of the Chemical Society, Chemical Communications, 1978
- Solvent Effects in the Oxidation of Hydrocarbons. II. Oxidations of Tetralin in Various SolventsBulletin of the Chemical Society of Japan, 1969
- Absolute rate constants for hydrocarbon autoxidation. VI. Alkyl aromatic and olefinic hydrocarbonsCanadian Journal of Chemistry, 1967
- Solvent Effects in the Reactions of Free Radicals and Atoms. IX. Effect of Solvent Polarity on the Reactions of Peroxy RadicalsJournal of the American Chemical Society, 1964
- THE INHIBITED AUTOXIDATION OF STYREN: PART IV. SOLVENT EFFECTSCanadian Journal of Chemistry, 1964
- SOLVENT EFFECTS ON HYDROCARBON AUTOXIDATIONSCanadian Journal of Chemistry, 1964
- Air Oxidation of Hydrocarbons.1 II. The Stoichiometry and Fate of Inhibitors in Benzene and ChlorobenzeneJournal of the American Chemical Society, 1955