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Effect of α-tocopherol and Trolox on the decomposition of methyl linoleate hydroperoxides

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Lipids

Abstract

To clarify the mechanisms of antioxidant action, the effect of α-tocopherol and its water-soluble carboxylic acid derivative, Trolox, was studied on the decomposition of methyl linoleate hydroperoxides (MeLoOOH). Decomposition rate and the distribution of autoxidation products formed from MeLoOOH were followed by analyzing the volatile and nonvolatile products by static headspace gas chromatography and normal-phase high-performance liquid chromatography, respectively. Both α-tocopherol and Trolox markedly inhibited the decomposition of MeLoOOH in a concentration-dependent way. In the absence of antioxidants, MeLoOOH was completely decomposed after incubation for 48 h at 60°C, and in the presence of equal molar concentration of antioxidants only 6–7% of initial MeLoOOH was decomposed even after 280 h of incubation. MeLoOOH produced 1.2% methyl linoleate hydroxy compounds (MeLoOH) in the presence of α-tocopherol and 3.8% in the presence of Trolox. Both antioxidants inhibited the formation of volatile decomposition products and the formation of ketodiene compounds. The hydroxy compounds may be formed by the reaction of alkoxy radical and hydrogen donating antioxidants. Conversion of MeLoOOH into stable MeLoOH demonstrated that the antioxidants α-tocopherol and Trolox trap alkoxyl radicals by H-donation.

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Abbreviations

GC:

gas chromatography

HPLC:

high-performance liquid chromatography

MeLo:

methyl linoleate

MeLoOH:

methyl linoleate hydroxy compounds

MeLoOOH:

methyl linoleate hydroperoxides

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Author notes

  1. Anu Hopia

    Present address: Department of Applied Chemistry and Microbiology, University of Helsinki, P.O. Box 27, FIN-00014 University of Helsinki, Finland

Authors and Affiliations

  1. Department of Food Science and Technology, University of California, 95616, Davis, California

    Anu Hopia, Shu-Wen Huang & Edwin N. Frankel

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  1. Anu Hopia
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  2. Shu-Wen Huang
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  3. Edwin N. Frankel
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Hopia, A., Huang, SW. & Frankel, E.N. Effect of α-tocopherol and Trolox on the decomposition of methyl linoleate hydroperoxides. Lipids 31, 357–365 (1996). https://doi.org/10.1007/BF02522920

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  • DOI: https://doi.org/10.1007/BF02522920

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