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.

A bacterium having close affinity with Pseudomonas flava was isolated from eucalypt leaves for its ability to utilize 1,8-cineole (1) as a carbon source. The bacterium is also capable of utilizing α-terpineol, camphor, isoborneol and geraniol but failed to grow on borneol, limonene and piperitone. Growth of the organism in mineral salts medium containing 1,8-cineole resulted in the formation of four oxidation products. Keto lactone (2), alcohols (3) and (4) and ketone (5) arereported as natural products arising from the oxidation of 1,8-cineole by the bacterium.

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Growth experiments of Pseudomonas flava, with cineole and various metabolites of cineole as the sole carbon and energy sources, yielded results which require alterations to a scheme by which P. flava is proposed to utilize these compounds. The optical purity of the metabolites obtained from achiral cineole has been reinvestigated.

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