Enzymatic synthesis of 1-caffeoylglycerol with deep eutectic solvent under continuous microflow conditions

Abstract

1-caffeoylglycerol (1-CG) is a hydrophilic ester with a high solubility, and has a strong activity to prevent skin cancer caused by ultraviolet. However, the current preparation process to synthesize 1-CG via transesterification from methyl caffeate (MC) and glycerin was not economic due to long reaction time or adding extra field. Therefore, an enzymatic synthesis with deep eutectic solvent chloride-urea (ChCl-urea) in a microreactor was firstly applied under continuous microflow condition to improve the productivity. A maximum 1-CG yield of 96.49% was obtained under the optimized conditions: temperature of 65 °C, flow rate of 2 μL/min, MC concentration of 50 g/L. Compared to the batch reactor, the reaction time reduced by 75%, the Km value decreased by 5/6, the reuse times of lipase increased by 2.29-fold, the external mass and transfer coefficients increased 10 times, which process was verified by numerical simulation. In addition, the produced 1-CG of 2 mg/mL has a high UV damage remediation ability of 75.16% using HaCaT cell model, which reveals 1-CG can repair the damage of cells radiated by the UV. Thus, this approach represents a convenient and cost-saving method to produce 1-CG using microfluidic biocatalysis.