Lipase-Catalyzed Synthesis of S-Naproxenal oleins

Abstract

S-Naproxenal oleins are compounds of S-Naproxen ((S)-2-(6-methoxy–2-naphthyl) propionic acid) and olein connected by an ester bond and can be used as potential prodrug in anti-inflammatory. In the present work, we describe for the first time the lipase-catalyzed synthesis of the S-Naproxenal oleins by transesterification between S-Naproxen and triolein in organic solvents medium. The ability of lipases to catalyze the transesterification between S-Naproxen and triolein was investigated. Only the lipase from Candida rugosa and the immobilized lipase B from Candida antarctica (Novozym 435) catalyzed the transesterification. The influences of reaction condition on the combined yield of S-Naproxenal diolein (NDO) and S-Naproxenal monoolein (NMO) were investigated. Water activity (aw) had an obvious influence on transesterification efficacy. A maximal combined yield of 23.1 % of S-Naproxenal diolein (NDO) and S-Naproxenal monoolein (NMO) was obtained under optimum condition. These results indicated the industrial potential of the operation scheme developed in this study.