Shikimic Acid, a Constituent of Tutsan Berries

Abstract

THE ripened seed capsules of tutsan (Hypericum androsemium) were dried, ground and extracted with petroleum ether (60°–80° C) followed by further extraction with acetone. The residue from the evaporated acetone extract, on vacuum sublimation, yielded a colourless solid, which crystallized from acetone–petrol in colourless plates m.p. 184°, with analysis C, 48.1; H, 5.8 per cent. C₇H₁₀O₅ requires C, 48.2; H, 5.8 per cent. Preliminary tests showed unsaturated and acidic properties. The infra-red spectrum proved to be identical with that of shikimic acid¹ (cyclohex-1-ene-3 : 4 : 5-triol-1-carboxylic acid) which is recorded in D.M.S. spectrum 2635.