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Literature DB >> 2640562

Autoxidation of methyl linoleate initiated by the ozonide of allylbenzene.

J C Ewing¹, J P Cosgrove, D H Giamalva, D F Church, W A Pryor.

Abstract

Allylbenzene ozonide (ABO), a model for polyunsaturated fatty acid (PUFA) ozonides, initiates the autoxidation of methyl linoleate (18:2 ME) at 37 degrees C under 760 torr of oxygen. This process is inhibited by d-alpha-tocopherol (alpha-T) and 2,6-di-tert-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 N2 in the presence of radical scavengers and found to be Ea = 28.2 +/- 0.3 kcal mol-1 and log A = 13.6 +/- 0.2; kd (37 degrees C) is calculated to be (5.1 +/- 0.3) X 10(-7) sec-1. Autoxidation data are also reported for ozonides of 18:2 ME and methyl oleate (18:1 ME).

Entities: Chemical Gene

Mesh：

Substances：

Year: 1989 PMID： 2640562 DOI： 10.1007/bf02535077

Source DB: PubMed Journal: Lipids ISSN： 0024-4201 Impact factor: 1.880

6 in total

1. STEREOISOMER FORMATION ON THE OZONIZATION OF ESTERS OF MONOUNSATURATED FATTY ACIDS.

Authors: O S PRIVETT; E C NICKELL
Journal: J Lipid Res Date: 1963-04 Impact factor: 5.922

2. Autoxidation of polyunsaturated fatty acids. Part I. Effect of ozone on the autoxidation of neat methyl linoleate and methyl linolenate.

Authors: W A Pryor; J P Stanley; E Blair; G B Cullen
Journal: Arch Environ Health Date: 1976 Jul-Aug

3. Radical production from the interaction of ozone and PUFA as demonstrated by electron spin resonance spin-trapping techniques.

Authors: W A Pryor; D G Prier; D F Church
Journal: Environ Res Date: 1981-02 Impact factor: 6.498

Review 4. Ozone: an overview of its toxicity in man and animals.

Authors: D B Menzel
Journal: J Toxicol Environ Health Date: 1984

5. A comparison of the rates of ozonation of biological antioxidants and oleate and linoleate esters.

Authors: D Giamalva; D F Church; W A Pryor
Journal: Biochem Biophys Res Commun Date: 1985-12-17 Impact factor: 3.575

6. The kinetics of the autoxidation of polyunsaturated fatty acids.

Authors: J P Cosgrove; D F Church; W A Pryor
Journal: Lipids Date: 1987-05 Impact factor: 1.880

6 in total

4 in total

Autoxidation of methyl linoleate initiated by the ozonide of allylbenzene.

1. STEREOISOMER FORMATION ON THE OZONIZATION OF ESTERS OF MONOUNSATURATED FATTY ACIDS.

2. Autoxidation of polyunsaturated fatty acids. Part I. Effect of ozone on the autoxidation of neat methyl linoleate and methyl linolenate.

3. Radical production from the interaction of ozone and PUFA as demonstrated by electron spin resonance spin-trapping techniques.

Review 4. Ozone: an overview of its toxicity in man and animals.

5. A comparison of the rates of ozonation of biological antioxidants and oleate and linoleate esters.

6. The kinetics of the autoxidation of polyunsaturated fatty acids.

1. Separation and spectral data of the six isomeric ozonides from methyl oleate.

2. The inhibitory effect of water on the Co2+ and Cu2+ catalyzed decomposition of methyl linoleate hydroperoxides.

3. Reactions of dinitrogen pentoxide and nitrogen dioxide with 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine.

4. Production of the Criegee ozonide during the ozonation of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine liposomes.