Novel hydroxylated enantiomers of (-) 3a,6,6,9a-tetramethylperhydronaphtho[2,1-b]furan as perfuming agents derived from a fungal fermentation process.

Abstract

(−) 3a,6,6,9a-tetramethylperhydronaphtho[2,1-b]furan (ambrox) is a strong aromatic compound used widely in a variety of perfumery applications and is highly prized for its musky odor. We report novel polar metabolites of (−)3a,6,6,9a-tetramethylperhydronaphtho[2,1-b]furan prepared by a novel process of microbial fermentation using a fungi, Fusarium lini, of unique structures that would be difficult to predict opening up the possibilities of their chemical synthesis. The polar metabolites discovered have stronger aromatic characteristics and offer a new highly prized odiferous characteristic quite different from that of the parent compound and thus can be used in the preparation of perfumes, odor-masking and other odor-management applications.

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