Abstract
A component of the essential oil, obtained from the root of Aristolochia debilis SIEB. et Zucc., named aristolone, was assigned the molecular formula of C15H22O. Its catalytic, Wolff-Kischner, and lithium aluminium hydride reduction respectively afforded dihydroaristolone, C15H24O, deoxoaristolone, C15H24, and aristolol, C15H24O. Examination of the absorption spectra of these products suggested the presence of a double bond on one side and cyclopropane ring on the other side, conjugated with the ketone group in aristolone. Dehydrogenation of aristolone afforded 5-methyl-2-naphthol, while that of deoxoaristolone and aristolol gave 1-methylnaphthalene. It was thereby found that aristolone has a hydronaphthalene skeleton, that the ketone group is in its 2-position, and one methyl group is in 5-position. From these data, formula (VIII) or (IX) is proposed as the partial structure for aristolone.
