非催化无溶剂条件下没食子酸辛醇酯的高效合成。
Highly Efficient Synthesis of Chlorogenic Acid Oleyl Alcohol Ester under Non-Catalytic and Solvent-Free Conditions.
机构信息
Grain, Oil and Food Engineering Technology Research Center of the State Grain and Reserves Administration, Key Laboratory of Henan Province, Henan University of Technology, Lianhua Road 100, Zhengzhou 450001, China.
College of Food Science and Engineering, Henan University of Technology, Lianhua Road 100, Zhengzhou 450001, China.
出版信息
Molecules. 2023 May 8;28(9):3948. doi: 10.3390/molecules28093948.
As a natural polyphenolic compound, chlorogenic acid (CGA) has attracted increasing attention for its various biological activities, such as antioxidant, liver protection, intestinal barrier protection, and effective treatment of obesity and type II diabetes. However, the poor solubility of CGA in hydrophobic media limits its application in the food, drug and cosmetic industries. In order to obtain new hydrophobic derivatives, a highly efficient synthesis approach of CGA oleyl alcohol ester (CGOA) under non-catalytic and solvent-free conditions was developed in this study. The influences of reaction temperature, reaction time, substrate molar ratio, and stirring rate on the CGA conversion were investigated. The results showed that the optimal conditions were as follows: reaction temperature 200 °C, reaction time 3 h, molar ratio of CGA to oleyl alcohol 1:20, and stirring rate 200 rpm. Under these conditions, the CGA conversion could reach 93.59%. Then, the obtained crude product was purified by solvent extraction and column chromatography, and the purify of CGOA was improved to 98.72%. Finally, the structure of CGOA was identified by FT-IR, HPLC-MS and NMR. This study provides a simple and efficient strategy for the preparation of CGOA with the avoidance of catalysts and solvents.
作为一种天然多酚化合物，绿原酸（CGA）因其具有抗氧化、护肝、肠屏障保护等多种生物活性，以及对肥胖和 II 型糖尿病的有效治疗作用而受到越来越多的关注。然而，CGA 在疏水性介质中的溶解度较差，限制了其在食品、药物和化妆品行业的应用。为了获得新的疏水性衍生物，本研究开发了一种在非催化和无溶剂条件下高效合成 CGA 油醇酯（CGOA）的方法。考察了反应温度、反应时间、底物摩尔比和搅拌速度对 CGA 转化率的影响。结果表明，最佳条件为：反应温度 200°C，反应时间 3 h，CGA 与油醇摩尔比 1:20，搅拌速度 200 rpm。在此条件下，CGA 转化率可达 93.59%。然后，通过溶剂萃取和柱层析对得到的粗产物进行纯化，CGOA 的纯度提高到 98.72%。最后，通过傅里叶变换红外光谱（FT-IR）、高效液相色谱-质谱联用（HPLC-MS）和核磁共振（NMR）对 CGOA 的结构进行了鉴定。本研究为避免使用催化剂和溶剂制备 CGOA 提供了一种简单高效的策略。
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