Studies on Triterpenoids. X

Studies on the Constitution of Jegosapogenol. I. Derivatives and Se Dehydrogenation Products

Abstract

Structure of the triterpenoid, jegosapogenol, forming the parent structure of jegosaponin, the saponin contained in the fruit rind of Styrax japonica SIEB. ET ZUCC., was examined. Jegosapogenol, C₃₀H₅₀O₅, possesses a double bond, -CH=C<, and five primary or secondary hydroxyls, four of which are two pairs in adjacent positions, such as 1-2 or 1-3 positions, and the remainder is an inactive hydroxyl. Selenium dehydrogenation of jegosapogenol afforded 1, 2, 3, 4-tetramethylbenzene, 2, 7-dimethyl-naphthalene, 1, 2, 7-trimethylnaphthalene, and a product assumed to be a picene derivative of high melting point. It was thereby assumed that jegosapogenol Would be a pentacyclic triterpenoid of the α- or β-amyrin system.