Biotransformation of bicyclic terpenoid ketones towards compounds with olfactory properties

Abstract

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 O 2 and CrO 3 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-trimethylcyclohept-2-en-1-one is described as vegetable, celery-parsley-lovage. An uncommon and valuable application of Streptomyces has been presented.

Synthesis and olfactory evaluation of homologous series of (+)‐ and (−)‐carvone oxime ethers

“…This study is a continuation of our interest in the synthesis and olfactory evaluation of novel terpenoid derivatives . In our previous communication regarding olfactory properties of oxime ethers with the preserved fenchane system, we pointed out the potential of this class of compounds as fragrances.…”

Application of microorganisms towards synthesis of chiral terpenoid derivatives

“…In our previous papers, we described microbiological methods of obtaining new terpenoid derivatives with biological activity such as odorants (Kuriata et al 2010; Kuriata-Adamusiak et al 2011) and insect-feeding deterrents (Wincza and Lochyński 2012). …”

“…Despite several disadvantages, microbial transformations are commonly used in organic synthesis towards preparation of homochiral compounds used in agriculture, pharmaceutical, cosmetic, and food industry. In our previous papers, we described microbiological methods of obtaining new terpenoid derivatives with biological activity such as odorants (Kuriata et al 2010 ; Kuriata-Adamusiak et al 2011 ) and insect-feeding deterrents (Wincza and Lochyński 2012 ).…”