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Reaction products of α-tocopherol with methyl linoleate-peroxyl radicals

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Lipids

Abstract

α-Tocopherol was reacted with methyl linoleateperoxyl radicals at 37°C. The peroxyl radicals were generated by the reaction of methyl linoleate with a free radical initiator, 2,2′-azobis(2,4-dimethylvaleronitrile). The primary products of α-tocopherol with methyl linoleate-peroxyl radicals were isolated by reversephase and normal-phase high performance liquid chromatography (HPLC), and their structures were characterized by ultraviolet (UV), infrared (IR),1H and13C nuclear magnetic resonance (NMR) and mass spectrometry (MS). There were four stereoisomers of methyl 13-(8a-peroxy-α-tocopherone)-9(Z),11(E)-octadecadienoate and four stereoisomers of methyl9-(8a-peroxy-α-tocopherone)-10(E),12(Z)-octadecadienoate.

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Abbreviations

AMVN:

2,2′-azobis(2,4-dimethylvaleronitrile)

CD:

circular dichroism

HPLC:

high performance liquid chromatography

NMR:

nuclear magnetic resonance

MS:

mass spectrometry

GC/MS:

gas chromatography/mass spectrometry

IR:

infrared

UV:

ultraviolet

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Authors and Affiliations

  1. Department of Food Science, Faculty of Agriculture, Gifu University, 1-1 Yanagido, 501-11, Gifu City, Gifu, Japan

    Ryo Yamauchi, Tomoatsu Matsui, Koji Kato & Yoshimitsu Ueno

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  1. Ryo Yamauchi
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  2. Tomoatsu Matsui
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  3. Koji Kato
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  4. Yoshimitsu Ueno
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Yamauchi, R., Matsui, T., Kato, K. et al. Reaction products of α-tocopherol with methyl linoleate-peroxyl radicals. Lipids 25, 152–158 (1990). https://doi.org/10.1007/BF02544330

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  • DOI: https://doi.org/10.1007/BF02544330

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