Thienyl analogues of acyclic monoterpene alcohols and their biological activity

Abstract

AbstractBACKGROUND: Thienyl analogues of linalool, geraniol, nerol and citronellol were synthesised and their sensory and anti‐ microbial activities were investigated.RESULTS: The thienyl analogues of linalool, geraniol, nerol and citronellol, in which the isobutenyl moiety was replaced by a thiophene substituent, were synthesised from commercially available 2‐ and 3‐methylthiophenes and 2‐ and 3‐thiophenecarboxaldehydes. The olfactory properties of the new compounds were generally of the corresponding parent terpene type; however, their relative volatility determined by the headspace gas chromatography method was lower by a factor of 34–42 compared with the parent alcohols. Antimicrobial activity against Aspergillus niger and Penicillium expansum of some thienyl analogues of linalool was 1.5–3 times higher than that of linalool, with a minimum inhibitory concentration of 0.2–0.1 µL mL−1.CONCLUSION: Replacement of the isobutenyl moiety in acyclic monoterpene alcohols by a thienyl substituent results in the formation of new terpene analogues, some of which are interesting for perfumery and cosmetology because of their odour quality, tenacity and antimicrobial action. Copyright © 2009 Society of Chemical Industry