The pentadecanolide was biosynthesized in cyclohexane from 15-hydroxypentadecanoic acid, which as prepared from 15-tetracosenoic acid in Malania Olcifera Chum oil using lipase as catalyst. The effect of lipase activity on the lactonization was investigated. Lipases from fiften strains (13 strains of Candida and 2 strains of Penicillium) showed different catalytic effects to the synthesis reactions. The lipases from strains of Penicillium sp. and 4 strains of Candida sp. have catalytic lactonization activity, and the conversion ratio of substrate reached 88% by using lipase Candida sp.GXU01.
Synthesis of mcrocyclic lactones has been applied to medical and flavor field. Triglycerides(2) of ω-hydroxycarboxylic acids synthesized from malania oleifera chum oil(1) via ozonization and reduction, and compound 2 were catalytically transformed to macrocyctic lactones(3). This is a new method involving fewer steps and a 61% yield of cyclopentadecanolide was obtained. The reactive properties of macrolactonization of ω-hydroxycarboxylic acids were also studied. The result obtained shows that the priority order of macrolactonization as follows: 11-undecalactone>cyclotridecanolide>cyclopentadecanolide, i.e. the short chain ω-hydroxycarboxylic acids were preferentially cyclized.
