Enzymatic synthesis of structured lipids: Transesterification of triolein and caprylic acid ethyl ester

Abstract

Structured lipids were successfully synthesized by lipase-catalyzed transesterification (ester interchange) of caprylic acid ethyl ester and triolein. The transesterification reaction was carried out in organic solvent as reaction media. Eight commercially-available lipases (10% w/w substrates) were screened for their ability to synthesize structured lipid by incubating with 100 mg triolein and 78.0 mg caprylic acid ethyl ester in 3 mL hexane at 45~ for 24 h. The products were analyzed by reverse-phase high-performance liquid chromatography with evaporative light-scattering detector. Immobilized lipase IM60 from Rhizomucor miehei converted most triolein into structured lipids (41.7% dicapryloolein, 46.0% monocapryloolein, and 12.3% unreacted triolein). However, lipase SP435 from Candida antarctica had a higher activity at higher temperature. The reaction catalyzed by lipase SP435 yielded 62.0% dicapryloolein, 33.5% monocapryloolein, and 4.5% unreacted triolein at 55~ Time course, incubation media, added water, and substrate concentration were also investigated in this study. The results suggest that lipase-catalyzed transesterification of long-chain triglycerides and medium-chain fatty acid ethyl ester is feasible to synthesize structured lipids. JAOCS 73, 245-250 (1996).

Synthesis of structured triacylglycerols containing medium-chain and long-chain fatty acids by interesterification with a stereoespecific lipase from Mucor miehei.

“…The preparation of several grams of each structured TG can be achieved by increasing the concentration of both substrates in the interesterification reaction followed by the separation of the respective TGs through aluminum oxide column-chromatography The laboratory-scale preparation of these products allows the assay of their incorporation to more complex mixtures, providing the TGs are properiy stabilized to oxidation by antioxidants. The results reported in the present investigation demonstrate the potentials of lipase-catalyzed interesterif ¡cation of medium-chain fatty acid methyl esters and sn-2 long-chain polyunsaturated monoacylglycerols to obtain structured TGs (Huang & Akoh, 1996). Structured TGs containing medium-chain fatty acids at the sn-1, sn-3 positions and long-chain polyunsaturated fatty acid at the sn-2 position, such as eicosapentaenoic acid or docosahexaenoic acid, can provide both essential fatty acid and quick metabolic energy (Kritchevsky, 1995).…”

Modelling lipase‐catalysed transesterification of fats containing n‐3 fatty acids monitored by their solid fat content

“…Lipase-catalysed transesterification of oils and fats has been currently carried out, either in the presence of organic solvents [14][15][16], or in solvent-free media [11,[17][18][19][20][21][22][23][24]. The incorporation of n-3 PUFA into vegetable oils, catalysed by lipases, has been reported, namely by acidolysis reaction with free n-3 fatty acids or transesterification with methyl ester forms of n-3 PUFA or concentrates of triacylglycerols rich in n-3 PUFA [11,25,26].…”

Properties of immobilized lipase from Bacillus stearothermophilus MC7. Acidolysis of triolein with caprylic acid

“…A similar acidolysis reaction was described by Huang and Akoh (1996). Several different bacterial enzymes were applied and the best result was achieved using the Rhizomucor miehei lipase (CCO was 42%, COO was 46%).…”