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New oxidation products of 2,2,5,7,8-pentamethyl-6-chromanol

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Lipids

Abstract

Oxidation of the α-tocopherol model compound 2,2,5,7,8-pentamethyl-6-chromanol (1) byt-butyl hydroperoxide in chloroform, to which an alcohol has been added, produces 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanol as the major product. In the present study,1 was oxidized byt-butyl hydroperoxide in water-saturated chloroform to determine whether water would influence product formation in the same way as alcohols.

In addition to the usual products of oxidation such as 2-(3-hydroxy-3-methylbutyl)-3,5,6-trimethyl-1,4-benzoquinone (9), 5-formyl-2,2,7,8-tetramethyl-6-chromanol (11), the spirodimer and spirotrimer of1, three new products have been identified−2,2,7,8-tetramethyl-5-(2,2,5,7,8-pentamethyl-6-chromanoxy)methyl-6-chromanol (4), 5-hydroxymethyl-2,2,7,8-tetramethyl-6-chromanol (5) and 3-hydroxymethyl-2-(3-hydroxy-3-methylbutyl)-5,6-dimethyl-1,4-benzoquinone (7).

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Abbreviations

NOE:

Nuclear Overhauser Enhancement

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Authors and Affiliations

  1. Department of Organic Chemistry, University of New South Wales, P.O. Box 1, 2033, Kensington, N.S.W., Australia

    Cacang Suarna,  Sumarno, Derek Nelson & Peter T. Southwell-Keely

Authors
  1. Cacang Suarna
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  2. Sumarno
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  3. Derek Nelson
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  4. Peter T. Southwell-Keely
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Suarna, C., Sumarno, Nelson, D. et al. New oxidation products of 2,2,5,7,8-pentamethyl-6-chromanol. Lipids 23, 1129–1131 (1988). https://doi.org/10.1007/BF02535278

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  • DOI: https://doi.org/10.1007/BF02535278

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