High-yield synthesis of bioactive ethyl cinnamate by enzymatic esterification of cinnamic acid

• Published in: Food chemistry Vol. 190; pp. 629 - 633
• Main Authors: Wang, Yun, Zhang, Dong-Hao, Zhang, Jiang-Yan, Chen, Na, Zhi, Gao-Ying
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01.01.2016
• Subjects: Cinnamates - chemical synthesis; Cinnamates - chemistry; Cinnamic acid; Enzymes, Immobilized - chemistry; Esterification; Esterification - physiology; Ethyl cinnamate; Lipase; Reaction medium; Reaction medium; Ethyl cinnamate; Lipase; Cinnamic acid; Esterification
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2015.06.017

•Lipozyme TLIM-catalyzed esterification of cinnamic acid was studied.•This reaction was investigated in various media to increase ethyl cinnamate yield.•Ethyl cinnamate was synthesized in high yield by using isooctane as media.•The effects of several parameters on this reaction were analyzed. In this paper, Lipozyme TLIM-catalyzed synthesis of ethyl cinnamate through esterification of cinnamic acid with ethanol was studied. In order to increase the yield of ethyl cinnamate, several media, including acetone, isooctane, DMSO and solvent-free medium, were investigated in this reaction. The reaction showed a high yield by using isooctane as reaction medium, which was found to be much higher than the yields reported previously. Furthermore, several parameters such as shaking rate, water activity, reaction temperature, substrate molar ratio and enzyme loading had important influences on this reaction. For instance, when temperature increased from 10 to 50°C, the initial reaction rate increased by 18 times and the yield of ethyl cinnamate increased by 6.2 times. Under the optimum conditions, lipase-catalyzed synthesis of ethyl cinnamate gave a maximum yield of 99%, which was of general interest for developing industrial processes for the preparation of ethyl cinnamate.