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Chemical and enzymatic preparation of acylglycerols containing C 18 furanoid fatty acids
Author(s) -
Lie Ken Jie Marcel S. F.,
SyedRahmatullah M. S. K.
Publication year - 1995
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02537045
Subject(s) - chemistry , interesterified fat , glyceride , organic chemistry , triolein , lipase , diglyceride , soybean oil , triacylglycerol lipase , hydrolysis , hydroxymethyl , monoglyceride , monoacylglycerol lipase , fatty acid , glycidol , chromatography , catalysis , enzyme , biochemistry , receptor , endocannabinoid system
C 18 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 C 18 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 C 18 furanoid 1,2(2,3)‐diacylglycerol, selective hydrolysis of the furanoid triacylglycerol was achieved using procine pancreatic lipase in tris (hydroxymethyl) methylamine buffer. Interesterification of triolein with methyl C 18 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.