Abstract
Ozonic oxidation of hinokiic acid yielded a diketomonocarboxylic acid, C11H18(COCH3)COCOOH, and a ketonic substance, C13H20O, as a by-product. On further oxidation of the diketonic acid, following seven compounds were obtained: Ketonic aldehyde, C11H18(COCH3)CHO; ketonic acid, C11H18(COCH3)COOH and its methyl ester; unsaturated ketonic ester C14H19O(_??_1)COOCH3; keto-dicarboxylic ester, C11H18(COOH)COCOOCH3; dicarboxylic acid, C10H16(COOH)2, and its monomethyl ester; crystalline dicarboxylic acid, C11H18(COOH)2, and its dimethyl ester; and dicarboxylic acid, C9H16(COOH)2 (1, 1, 3-trimethylcyclohexane-2, 3-dicarboxylic acid), and its methyl ester. From these results, it has become clear that the double bond in hinokiic acid is situated between the 6- and 7-positions of the hydronaphthalene ring, and that the bridged bond between 5- and 9-positions form the unstable cyclopropane ring condensed to the saturated six-membered ring.
