Optimization of the reaction conditions in the lipase‐catalyzed synthesis of structured triglycerides

Abstract

Structured triglycerides of the ABA-type, containing one type of fatty acid (A) in the sn-1 and sn-3 positions and a second type of fatty acid (B) in the sn-2 position of the glycerol, were synthesized using lipases. The highest yields and purities were achieved in a two-step process, where a triglyceride of the B-type was subjected to an alcoholysis reaction in an organic solvent catalyzed by sn-1,3-regiospecific lipases yielding the corresponding 2-monoglyceride (2-MG). Using this strategy, e.g., 2-monopalmitin (2-MP) was obtained in up to 88% yield at >95% purity by crystallization. Esterification of 2-MP with oleic acid resulted in the formation of 1,3-oleyl-2-palmitoylglycerol in up to 72% yield containing 94% palmitic acid in the sn-2 position. The best lipases were from Rhizomucor miehei, Rhizopus delemar, and Rhizopus javanicus. Water activity, solvent, and carrier for lipase immobilization strongly influenced the yield and purity of the products in both steps. Futhermore, 2-MG from fish oil were produced by alcoholysis in up to 84% yield at >95% purity. JAOCS 75, 1527-1531 (1998). FIG. 3. Time course of the formation of 1,3-oleyl-2-palmitoyl-glycerol (OPO) from 2-MP with oleic acid in n-hexane with Lipozyme. For abbreviations, see Figure 1.

PPARα signal pathway gene expression is associated with fatty acid content in yak and cattle longissimus dorsi muscle

“…These results agree with those of previous studies, which reported that yaks had more unsaturated fatty acids in their longissimus dorsi muscle than did cattle (Li et al, 2008;Wan et al, 2012). MUFA has a positive effect on the absorption of other fatty acids, so that it can increase the mobility and metabolism of fat globules (Schmid et al, 1998). Yak meat contained a certain amount of EPA and DHA, which were not detected in beef.…”

Potential Applications of Green Technologies in Olive Oil Industry

“…The structured lipid produced at optimal conditions had 7.2% caprylic acid, 69.6% oleic acid, 21.7% linoleic acid and 1.5% palmitic acid at the sn-2 position. Another structured lipid used as a constituent of infant formulas, consisting mainly of UPU triglycerides (U=unsaturated acyl chains, P=palmitic acyl group), can be prepared by lipase catalyzed reactions of fractionated palm oil, rich in tripalmitin, and oleic acid from olive oil (Schmid et al, 1998).…”

Effect of water content and temperature onCarica papayalipase catalyzed esterification and transesterification reactions

“…For lipid synthesis, reactions performed with water-free substrates and in solvent-free systems, a minimal hydration of the lipase is needed to maintain its activity toward ester synthesis [29][30][31]. Because of this, in the present study the water was limited to that present in the C. papaya latex preparation.…”