By chemical and spectroscopic methods,
carnaubadiol, C31H54O2, a constituent of
carnauba wax, was shown to contain one secondary and one tertiary hydroxyl
group, and one isopropenyl group. A series of degradative reactions yielded a
heptanorketone, identical with the known 3β-acetoxyhexanordammaran-20-one,
previously obtained from dammarenediol. The structure and configuration of the
side-chain were established by oxidation of dihydrocarnaubadiol to the known
(-)-(S)-5,6-dimethylheptan-2-one. Carnaubadiol was thus shown to be 24β-methyl-
dammar-25-ene-3β,20ξ-diol.