Carnaubadiol, a triterpene from carnauba wax

Abstract

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.