トコフェロール酸化生成物に関する研究 (第1報) : α-およびδ-トコフェロール二量体の抗酸化性

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α- and δ-Tocopherols were oxidized with p-benzoquinone according to the method by McHale and Green or with cupric palmitate. The dimeric oxidation products were then isolated by preparative thin layer chromatography. UV absorption, IR absorption, mass and NMR spectra of the isolated products were determined. Autoxidation of hydrogenated whale oils with these tocopherol dimers was measured by Active Oxygen Method. Two kinds of oxidized tocopherol dimers were produced during the oxidation of α- and δ-tocopherols. One is the dimers derived from the oxidation of α- and δ-tocopherols with cupric palmitate (α-2 & δ-3), having phenolic hydroxyl group. Another is the dimer obtained from the p-benzoquinone oxidation products of α-tocopherol (p-1), having no phenolic hydroxyl group. The hydroxyl dimers indicated antioxidative power, especially the dimer derived from the oxidation of δ-tocopherol (δ-3) had a strongly antioxidative property although its activity was less than that of δ-tocopherol. The hydroxyl dimer of α-tocopherol (α-2) had only a small effect on the protective action against the oxidation of hydrogenated whale oil, while the dimer (p-1) did not have antioxidative activity. From the structural study of δ-3, this had the following formula :
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