Novel tocopheryl compounds XX. 1,3,8-Trioxaphenanthrenes derived from γ-tocopherol |
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Authors: | Christian Adelwö hrer |
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Affiliation: | University of Natural Resources and Applied Life Sciences, Department of Chemistry, Muthgasse 18, A-1190 Vienna, Austria |
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Abstract: | Condensation of γ-tocopherol with aldehydes provides 2,4-disubstituted 1,3,8-trioxaphenanthrenes in a simple one-pot reaction. The reaction proceeded under acid catalysis according to a two-step alkylation-acetalisation mechanism in yields between 58 and 81%. The title compounds are precursors for the thermal generation of ortho-quinone methides, which can be in situ reduced to give antioxidants of the 5a-substituted α-tocopherol-type. The products were analytically characterized by NMR and HRMS. |
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Keywords: | Tocopherol Vitamin E Antioxidants ortho-Quinone methide |
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