Lipase-catalyzed one-step regioselective synthesis of 1,2-dioctanoylgalloylglycerol in a solvent-free system: Optimization of reaction conditions and structural elucidation

Abstract

A multi-functional galloylated structured lipid, 1,2-dioctanoylgalloylglycerol (DOGG), was synthesized enzymatically via a regioselective transesterification of propyl gallate and trioctanoate using an immobilized food-grade Candida antarctica lipase B (Lipozyme® 435) as the biocatalyst under solvent-free condition. The variables that affect the reaction, including reaction temperature, substrate ratio, reaction time, and enzyme load, were evaluated and optimized using Taguchi method and response surface methodology. Both methods predicted the same optimal reaction condition, resulting in a 68.8 ± 1.3% DOGG yield with reaction selectivity of 82.9 ± 0.6% at 90 °C, 25/1 trioctanoate/PG (mol/mol), 72 h reaction, and 25% enzyme load relative to the total substrate weight. The structure of the reaction product was elucidated using NMR spectroscopy and ESI-HRMS, confirming the regioselectivity of the reaction. Enzyme retained 50% of its activity after 5 cycles of reuse. It is feasible to synthesize DOGG as a potential antioxidant and nutraceutical using Lipozyme® 435.