Journal ArticleDOI
Analysis of autoxidized fats by gas chromatography-mass spectrometry: I. Methyl oleate.
E. N. Frankel,William E. Neff,W. K. Rohwedder,B. P. S. Khambay,R. F. Garwood,B. C. L. Weedon +5 more
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In this paper, a structural investigation of methyl oleate was carried out by gas chromatography-mass spectrometry (GC-MS) of trimethylsilyl (TMS) ether derivatives.Abstract:
A structural investigation of autoxidation products of methyl oleate was carried out by gas chromatography-mass spectrometry (GC-MS) of trimethylsilyl (TMS) ether derivatives. GC-MS using computer plots of selected masses afforded structural assignments of GC peaks due to incompletely resolved mixtures. This method provided evidence of epoxy and keto esters which are not completely separated from the main components consisting of the TMS derivatives of the allylic hydroxy esters. Use of an MS-computer system also showed that the hydroxyoctadecanoate TMS ethers were partially separated by GC. The use of synthetic hydroxyoctadecanoates for the first time enabled us to demonstrate the quantitative reliability of a GC-MS computer summation approach to analyze the isomeric composition of oleate hydroperoxides (as the saturated TMS ether derivatives). Consistently higher concentrations were found of the 8- and 11-hydroperoxides than of the 9- and 10-hydroperoxides. Minor products of autoxidation identified by GC-MS include allylic enones, isomeric epoxyoctadecanoates, dihydroxyctadecenoates, and dihydroxyoctadecanoates.read more
Citations
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Journal ArticleDOI
Mechanisms of free radical oxidation of unsaturated lipids
TL;DR: The mechanisms of these primary reaction steps has been the focus of extensive research over the past fifty years, and the current level of understanding of these transformations is the subject of this review.
Journal ArticleDOI
Oxygen radical chemistry of polyunsaturated fatty acids
TL;DR: Although homolytic reactions of PUFA hydroperoxides have received the most attention, hydroper oxides are also susceptible to heterolytic transformations, such as nucleophilic displacement and acid-catalyzed rearrangement.
Journal ArticleDOI
Review. Recent advances in lipid oxidation
TL;DR: In a major pathway of the autoxidation of methyl linolenate, peroxyl radicals of the internal hydroperoxides undergo rapid 1,3-tyclisation to form hydroperoxyepidioxides as mentioned in this paper.
Journal ArticleDOI
Lipid oxidation: Mechanisms, products and biological significance
TL;DR: In this paper, an acid-acetalation decomposition procedure was used to evaluate lipid oxidation products as sources of malonaldehyde and its biological effects due to crosslinking.
References
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Isolation and Structure of Two Prostaglandin Endoperoxides That Cause Platelet Aggregation
TL;DR: Platelet aggregation induced by thrombin was accompanied by release of material reducible by stannous chloride into prostaglandin F(2alpha), thus indicating the involvement of endogenous prostaglandsin endoperoxides in platelet aggregation.
Journal ArticleDOI
Autoxidation of polyunsaturated fatty acids: II. A suggested mechanism for the formation of TBA-reactive materials from prostaglandin-like endoperoxides.
TL;DR: The nature and mechanism of formation of the thiobarbituric acid (TBA)-reactive material produced in the autoxidation of polyunsaturated fatty acids (PUFA) or their esters has been studied.
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Autoxidation of methyl linoleate. Separation and analysis of isomeric mixtures of methyl linoleate hydroperoxides and methyl hydroxylinoleates
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