脂溶性绿原酸月桂酸酯的研制及表征

Preparation and Characterization of Liposoluble Chlorogenic Laurate

绿原酸是一种天然酚类抗氧化剂,已应用于食品、医药、日用化工等行业中.然而,其易溶于水难溶于油的特性使其应用受到了限制.文中对绿原酸进行了改性,即在碱性催化剂催化的条件下使其与月桂酰氯进行非水相的酯化反应,得到了脂溶性的绿原酸月桂酸酯.经过单因素及正交试验,确定了最佳合成条件为:以N,N-二甲基甲酰胺作为溶解、稀释剂,绿原酸/月桂酰氯/三乙胺的摩尔比为1∶1∶1.5,温度控制在35℃,反应时间8 h.在此条件下,可得到微黄色粉状固体产物绿原酸月桂酸酯,其产率为81.24%.文中还通过UV-V is、IR、ESI-MS1、HNMR及元素分析法对产物的结构进行了表征,并采用量子化学计算论证了该分子修饰的可行性和合理性.

Chlorogenic acid （ CGA）, a kind of natural antioxidant, has been widely applied to the fields of food, medicine and daily chemical industry. However, its application is restricted by its good water-solubility and weak liposolubility. In this research, liposoluble chlorogenic laurate （CGL） was synthesized by the acylation with lauroyl chloride （LC） in the existence of alkali catalyst in non-water phase, and yellowish CGL powders with a yield of 81.24% were obtained under the optimal synthesis conditions determined via single-factor tests and orthogonal experiments, that is, carrying out the acylation at 35℃ for 8h with a nCGA： nLC： nTEA ratio of 1： 1：1.5 and with dimethylformamide as the solvating agent and the thinner. Then, the structure of CGL was characterized by means of UV-Vis, IR, ESI-MS, ^1HNMR and element analytical method. The feasibility and rationality of the molecule modification for CGA were finally demonstrated by the method of quantum chemistry calculation.