Abstract
a-Tocopherol was reacted with cholesteryl linoleate hydroperoxides (Ch18:2-OOH) in the presence of an iron-chelate, Fe(III) acetylacetonate, at 37 degrees C in benzene. The reaction products were isolated and identified as four positional isomers of cholesteryl (8a-dioxy-alpha-tocopherone)-epoxyoctadecenoates and two positional isomers of cholesteryl (8a-dioxy-alpha-tocopherone)-octadecadienoates. The result indicates that the peroxyl radicals from Ch18:2-OOH react with the 8a-carbon radical of alpha-tocopherol to form the addition products.
MeSH terms
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Antioxidants / chemical synthesis*
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Cholesterol Esters / chemistry*
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Chromatography, High Pressure Liquid
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Free Radicals / chemistry
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Gas Chromatography-Mass Spectrometry
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Hydroxybutyrates / chemistry
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Iron Chelating Agents / chemistry
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Isomerism
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Lipid Peroxidation
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Pentanones / chemistry
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Peroxides / chemistry*
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Spectrophotometry, Ultraviolet
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Vitamin E / analogs & derivatives*
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Vitamin E / chemical synthesis
Substances
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Antioxidants
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Cholesterol Esters
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Free Radicals
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Hydroxybutyrates
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Iron Chelating Agents
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Pentanones
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Peroxides
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Vitamin E
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acetyl acetonate
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cholesteryl linoleate