Synthesis of novel resveratrol nervonic acid ester using a solvent-free mechanochemical method: Improved lipophilicity, thermostability, and oxidation stability

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.