Synthesis and antimicrobial activity of long-chain 3,4-Epoxy-2-alkanones

Sci Pharm. 2010 Oct-Dec;78(4):745-51. doi: 10.3797/scipharm.1009-02. Epub 2010 Oct 9.

Abstract

3,4-Epoxy-2-dodecanone, a major component in the preorbital gland of the African grey duiker (Sylvicapra grimmia), showed antimicrobial activity in preliminary tests. The C(11) to C(17) homologues of this compound were prepared and their activity against several pathogenic dermal bacteria and fungi was tested. 3,4-Epoxy-2-dodecanone and 3,4-epoxy-2-tridecanone inhibited the growth of Trichophyton mentagrophytes at 25 Îg/mL. Moderate inhibition of the growth of the bacteria Propionibacterium acnes and the lipophilic yeast, Pityrosporum ovale, was seen for several of the homologues.

Keywords: 3,4-Epoxy-2-alkanones; Antifungal activity; Propionibacterium; Trichophyton.