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Updated: May 20, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Synthesis of novel resveratrol nervonic acid ester using a solvent-free mechanochemical method: Improved
Tian Li1, Manzhu Liang2, Zhenyuan Li2
1Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences/Key Laboratory of Agro-Products Processing, Ministry of Agriculture, Beijing 100194, PR China; Key Laboratory of Food Nutrition and Functional Food of Hainan Province, School of Food Science and Engineering, Hainan University, Haikou 570228, PR China.
Abstract:
Resveratrol (RES), a polyphenol with strong antioxidant properties, has limited applications in the food industry because of its poor lipophilicity and stability. A new, green, simple, effective, and universally applicable approach was presented for synthesizing resveratrol nervonic acid (NA) ester (RNE) using a solvent-free mechanochemical method. The conversion, purity, and yield of RNE reached 95.85 %, 91.28 %, and 80.78 %, respectively. High yields of alcoholic fatty acid esters (94.54-99.48 %) were also achieved. The RNE synthesis mechanism involved the formation of a 4'- monoester, followed by a 4', 5- diester, and ultimately a 3,4',5- triester. RNE was a slightly yellowish solid with a composition of 3,4',5 -triester (87.19 %), 3/5,4'-diester (11.61 %), and 4'-monoester (1.2 %). Compared to RES, RNE exhibited significantly improved lipophilicity (204.08 times), thermostability (148.9 °C), and oxidation stability (1.05-1.60 times). This study provided a novel strategy for the synthesis of alcoholic fatty acid esters, expanding the application of RES in the food industry.
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