Studies on Antioxidants. I. : Syntheses of ω, ω'-Bis(2, 3, 4-trihydroxyphenyl)alkanes and Their Antioxidant Activities

Abstract

ω, ω'-Bis(2, 3, 4-trihydroxyphenyl)alkanes, which are pyrrogallol derivatives, with zero to 10 carbons in the chain were systematically synthesized and their antioxidant action against vitamin A acetate was examined. The starting material used was pyrrogallol trimethyl ether which was condensed with dicarboxylic chloride by the Friedel-Crafts reaction to form ketones, which were catalytically reduced, and finally demethylated to the objective compounds. For the examination of the antioxidant action of these derivatives, vitamin A acetate was dissolved in pure ethyl laurate to obtain a vitamin A oil, a definite amount of each of these derivatives was added to the oil, and the decomposition rate of vitamin A acetate was compared with that of the control in the absence of the antioxidation agent. Some of the compounds showed a fairly good effect compared to nordihydroguaiaretic acid.