Low-Calorie Triglyceride Synthesis by Lipase-Catalyzed Esterification of Monoglycerides

Article abstract of DOI:10.1007/BF02546203

Monoglycerides of erucic acid (C_22:1, Δ13), prepared by conventional methods, were reacted with caprylic acid (octanoic acid, C_8:0) by using lipases as catalysts with the intention of synthesizing a triglyceride that contains two molecules of caprylic acid and one molecule of erucic acid (caprucin).The reaction was carried out by mixing lipase powder, a small quantity of water, and the reactants in a temperature-controlled stirred batch reactor.Organic solvents or emulsifying agents were not required.When the nonspecific lipase from Pseudomonas cepacia was used, a yield of approximately 37percent caprucin was obtained, together with a complex mixture of di- and triglycerides that resulted from the random transesterification of the erucic acid.The fatty acid-specific lipase from Geotrichum candidum promoted minimal transesterification of erucic acid and resulted in a yield of 75percent caprucin and approximately 10percent interesterification products.Lipase from Candida rugosa exhibited a similar, although less pronounced, specificity to that from G. candidum and promoted more transesterification of erucid acid.Optimum conditions for G. candidum lipase were at 50 deg C and an initial water content of 5.5percent.After the reaction, erucic acid was converted to behenic acid by hydrogenation, thereby converting caprucin into caprenin, a commericially available low-calorie triglyceride. - Key words: Behenic acid; caprenin; caprucin; erucic acid; lipase; monoglyceride; synthesis; triglyceride