Chemical and enzymatic preparation of acylglycerols containing C18 furanoid fatty acids

Abstract

C18 furanoid triacylglycerol [glycerol tri-(9,12-epoxy-9,11-octadecadienoate)] was prepared by chemical transformation of triricinolein isolated from castor oil. The procedure involved oxidation, epoxidation and cyclization of the epoxy-keto intermediate with sodium azide and ammonium chloride in aqueous ethanol. The furanoid triacylglycerol was also obtained by esterification of C18 furanoid fatty acid with glycerol using Novozyme 435 (Novo Nordisk A.S., Bagsvaerd, Denmark) as biocatalyst. When Lipozyme (Novo Nordisk A.S.) was used, a mixture of the furanoid 1(3)-rac-monoacylglycerol and 1,3-diacylglycerol was obtained. In order to obtain the C18 furanoid 1,2(2,3)-diacylglycerol, selective hydrolysis of the furanoid triacylglycerol was achieved using porcine pancreatic lipase in tris(hydroxymethyl) methylamine buffer. Interesterification of triolein with methyl C18 furanoid ester in the presence of Lipozyme showed maximum incorporation of 34% of furanoid fatty acid. Extension of the interesterification to vegetable oils (olive, peanut, sunflower, corn and palm oil) allowed a maximum of 24% furanoid acid incorporation to be achieved.