油脂の酸化防止に關する研究 : (第6報)ω, ω-Bis-(3, 4-dihydroxyphenyl) Alkanes類の合成(その1)

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The following • ω, ω-bis-(3, 4-dihydroxyphenyl) alkanes similar to NDGA were synthesized to make one approach to the solution of the relationship of chemical structure for the antioxidant activity. Compounds mp. Number 1, 3-Bis-(3, 4-dihydroxyphenyl) propane 117_??_119° VI 1, 4-Bis-(3, 4-dihydroxyphenyl) butane 138_??_139° XVIII 1; 6-Bis-(3, 4-dihydroxyphenyl) hexane 133_??_134° XXII 1, 9-Bis-(3, 4-dihydroxyphenyl) nonane 106_??_108° XXV 1, 10-Bis-(3, 4-dihydroxyphenyl) decane 129_??_131° XXIX (1) The synthesis of VI. 3, 4, 3, 4-Tetramethoxy chalcone (LLI), prepared by the con-densation of veratric aldehyde (I) with acetoveratrone (II), was reduced by the catalytic hydrogenation and CLEMMENSEN method successively and the reduction product (V) was dertiethylated with HI to give VI. (2) The synthesis of XVIIL 1, 4-Diveratrylbutane (XVII) was prepared by the method of HAWORTH et al. (4) shown in the schema XI → XVII and demethylated with HI to give XVIII. (3) The synthesis of XXII. Veratrol was condensed with adipyl chloride in the presence of AlC13 and the resulting 1, 4-diveratroyl-butane (XIX) was reduced to XXI by the WOLFF-KISHER method, and then XXII was obtained through the demethylation with HI. (4) The synthesis of XXV. Azelayl chloride and veratrol were condensed as the same way as in the case of adipyl chloride and veratrol and the resulting 1, 7-diveratroylheptane (XXIII), was hydrogenated by the CLEMMENSEN reduction. The demethylation with HI gave XXV. (5) The synthesis of XXIX. The condensation of polymeric sebacic anhydride with vertrol gave 1, 8-diveratroyloctane (XXVI) and ω-veratroylpelargonic acid (XXVII), mp. 85_??_87°. The former was treated as in the case of XXIII to yield XXIXX. 46%. The antioxidant activity of these bis-(dihydroxyphenyl) alkanes will be discussed in the following papers. The authors wish to express their appreciations to Professor Dr. Y. SUMIKI for his, guidance and advice.
社団法人日本農芸化学会の論文

油脂の酸化防止に關する研究 : (第6報)ω, ω-Bis-(3, 4-dihydroxyphenyl) Alkanes類の合成(その1)

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