Studies of the optically active compounds of Anacardiaceae exudates. III. The long-chain Alicyclic Keto Alcohols from the exudate of Campnosperma auriculata Hook. F

Abstract

Terentang oil, the exudate from the Malayan tree Campnosperma auriculata Hook. f., contains optically active substances closely related to the optically active component of Tigaso oil. These substances are assigned the general structure I and differ among themselves only in the amount and location of unsaturation in the C₁₉ aliphatic side chain. All of them by heating with ethanolic alkali and subsequent hydrogenation give a product which is mainly 3-nonadecyl phenol. Catalytic hydrogenation alone produces (+)-3-hydroxy-3-nonadecylcyclohexanone and thence by dehydration 3-nonadecylcyclohex-2-enone. Hydrocampnospermonol is a convenient starting material for the preparation of the reference substances 3-nonadecyl phenol and 3-nonadecylcyclohexanone.