Studies on the Chemical Constituents of the Plants of Coniferae and Allied Orders. XXXVIII

Some time ago, Kariyone and Sawada found a flavonoid from the leaves of Chamaecyparis obtusa ENDLICHER and named it hinokiflavone, giving a formula of C30H12O4(OH)6. In spite of the fact that this composition agrees with that of demethylated compound of bis-flavonoid, ginkgetin and sciadopitysin, it was found to be not identical and these workers assumed that this substance must be a bis-flavonoid with linkage positions different from that of known bis-flavonoids. It was established by the present series of work that the formula of hinokiflavone is C30H15O5(OH)5. Decomposition of hinokiflavone with 25% potassium hydroxide solution afforded p-hydroxyacetophenone, a flavonoid of C23H13O4(OH)3, phloroglucinol, and a phenolic ketone of C14H12O5.