Biotransformation of bicyclic terpenoid ketones towards compounds with olfactory properties
2011
Kuriata‐Adamusiak, Renata | Strub, Daniel | Szatkowski, Paweł | Lochyński, Stanisław
In the search of new chiral derivatives with olfactory properties we performed stereoselective reactions mediated by different strains of microorganisms such as Aspergillus niger, Fusarium oxysporum, Fusarium culmorum, Hansenula anomala and Streptomyces lusitanus StA. Oxidation of (+)‐3‐carene with O2 and CrO3 led to (+)‐3‐carene‐5‐one and (−)‐3‐carene‐2,5‐dione, which were used as substrates for biotransformation. As a result, five odoriferous derivatives were characterized by spectroscopic methods. This is the first time that their olfactory properties have been determined. 3,6,6‐trimethylcyclohept‐2‐en‐1‐one is described as balsamic with a turpentine note, whereas the odour of 3,6,6‐trimethyl‐cyclohept‐2‐en‐1‐one is described as vegetable, celery–parsley–lovage. An uncommon and valuable application of Streptomyces has been presented.
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