Preparation and characterization of derivatives of isoricinoleic acid and their antimicrobial activity

Methylisoricinoleate (methyl-9-hydroxy-cis-12-octadecenoate) (I) has been derivatized to yield new fatty acid derivatives analogous to those obtained from the ricinoleic acid of castor oil. These derivatives include 1,9-dihydroxy-12-octadecene (II); 1,9-diacetoxy-12-octadecene (III); 12,13-epoxy-1,9-diacetoxyoctadecane (IV); 9-cyanoethoxy-1-hydroxy-12-octadecene (V); 1-morpholine-9-hydroxy-12-octadecene (VI), and 1-morpholine-9-cyanoethoxy-12-octadecene (VII). Structures of these compounds were established by chemical and spectral data. The compounds V, VI and VII showed antifungal activity againstAlternaria sp.,Helminthosporium sp.,Penicillium citrinum, Fusarium oxysporum, Aspergillus ochraceous, A. flavus, A. niger, Actinomyces sp. andCladosporium harbarum.