1,3-Dimethyl-2-oxabicyclo[2,2,2]-octane-3-methanol and 1,3-Dimethyl-2-oxa-bicyclo[2,2,2]octane-3-carboxylic Acid, Urinary Metabolites of 1,8-Cineole

Abstract

Examination of urinary metabolites from brushtail possums (Trichosurus νulpecula) maintained on a diet of fruit impregnated with 1,8-cineole (1) yielded two new compounds shown by spectral analysis, synthesis and interconversion to be 1,3-dimethyl-2-oxabicyclo[2,2,2]octane-3-methanol (2) (9-hydroxycineole) and 1,3-dimethyl-2-oxabicyclo[2,2,2]octane-3-carboxyic acid (3) (cineol-9-oic acid).