Dec 1, 1982

Oxidation of lipids: III. Oxidation of methyl linoleate in solution

Lipids
Y YamamotoY Kamiya

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.

  • References4
  • Citations15

Citations

Mentioned in this Paper

Alveolar Ventilation Function
Hydrogen Peroxide
Area 4a of Vogts
octadecadienoic acid
2-3A-C
Uptake
Linolelaidic Acid
methyl linoleate
Oxidation
Area 5a of Vogts

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