The hydroxycineole (2) and cineolic acid (3) obtained as urinary metabolites from the brushtail possum (Trichosurus vulpecula) after the ingestion of l,8-cineole (1), are partial racemates. The compounds have been examined by gas chromatographic analysis over chiral stationary phases, and by the synthesis of optically pure enantiomers. Female possums show different enantiomeric ratios from males. Possible advantages to the animal in the use of a partial racemate as a pheromone are discussed.

The four diepoxides of limonene have been synthesized and separated, and their distinguishing spectral characteristics are described.

2,9-Dihydroxy-1,8-cineole (7a) and the corresponding 2,10-dihydroxy compound (8a) are present in the urine of brushtail possums fed a diet enhanced with 1,8-cineole (1). Chemical syntheses of these two novel metabolites are described.

7-Hydroxy-1,8-cineole (3a) and the corresponding carboxylic acid (3b) have been isolated from the urine of brushtail possums ( Trichosurus vulpecula: Marsupialia ) fed a diet enhanced with 1,8-cineole. Chemical syntheses of these two novel metabolites are described.

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