Lipase-catalyzed synthesis of capsaicin analogs by transacylation of capsaicin with natural oils or fatty acid derivatives in n-hexane

Transacylation of capsaicin with triolein using a commercial lipase gave ol vanil in an 85% yield at 70 degrees C for 144 h. When olive oil was employe d, the major product was olvanil (62%). Safflower oil gave a mixture of olv anil (39%) and linoleoyl vanillylamide (32%). Perilla oil gave linolenoyl v anillylamide (13%). Myristic acid and its methyl ester could be used as an acyl donor, and myristoyl vanillylamide was obtained in 20-78% using severa l lipases.