alpha-Tocopherol oxidation mediated by superoxide anion (O2-). II. Identification of the stable alpha-tocopherol oxidation products.
The present paper describes the identification of two stable end products of alpha-tocopherol oxidation that were previously detected among the products of the reaction of alpha-tocopherol with superoxide anion (O2-) under aprotic conditions. One compound, previously designated compound A, was identified as trans-7-hydroxy-trans-8,8a-epoxy-alpha-tocopherone, and the other, designated compound B, was identified as cis-7-hydroxy-cis-8,8a-epoxy-alpha-tocopherone. It was also observed that under protic conditions (10% water in acetonitrile) the reaction of alpha-tocopherol with O2- did not produce compounds A and B, but rather alpha-tocopheryl quinone, alpha-tocopherol dimer, alpha-tocopherol dihydroxy dimer, and the previously designated compound C. Compound C was identified in the present study as alpha-tocopheryl-quinone-2,3-epoxide.
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Department of Food Science and Nutrition, University of Minnesota, St. Paul 55108.
Csallany
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D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013055:Spectrophotometry, Infrared; D013481:Superoxides; D014810:Vitamin E / Q000737:chemistry*
D007202:Indicators and Reagents; D013481:Superoxides; D014810:Vitamin E