Mechanism of inhibition of lipid peroxidation by γ-terpinene, an unusual and potentially useful hydrocarbon antioxidant

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DOIResolve DOI: http://doi.org/10.1021/jf020993f
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TypeArticle
Journal titleJournal of Agricultural and Food Chemistry
ISSN0021-8561
Volume51
Issue9
Pages27582765; # of pages: 8
Subjectalpha tocopherol; antioxidant; hydrocarbon; linoleic acid; para cymene; radical; terpinene; antioxidant activity; article; chemical reaction; lipid peroxidation; oxidative stress; Fatty Acids; Free Radicals; Linoleic Acid; Lipid Peroxidation; Lipid Peroxides; Monoterpenes; Oxidation-Reduction; Terpenes
Abstractγ-Terpinene (TH), a monoterpene hydrocarbon present in essential oils, retards the peroxidation of linoleic acid (LH). The peroxidation of TH has been shown to yield p-cymene as the only organic product in a chain reaction in which the chain carrier is the hydroperoxyl radical, HOO.. The peroxidation of LH is well-known to be a chain reaction in which the chains are carried by linoleylperoxyl radicals, LOO., and the products are linoleyl hydroperoxides. The retardation of LH peroxidation by TH has been found to be due to rapid chain termination via a very fast cross-reaction between HOO. and LOO. radicals. This antioxidant mechanism is completely different from the mechanism of antioxidant action of vitamin E. Since vitamin E becomes a prooxidant at high concentrations, the addition of essential oils containing TH to edible lipids may provide an alternative or supplementary strategy for obtaining large increases in their oxidative stability and shelf life, something that cannot be achieved by simply adding more and more vitamin E.
Publication date
PublisherAmerican Chemical Society
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276571
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Record identifier01c68393-c33f-4aae-ab36-4d202f4d3f27
Record created2015-10-13
Record modified2017-03-15
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