Study On The Synthetic Process Of Resveratrol Laurate

Resveratrol is a natural polyphenolic substance with physiological activity ofanti-tumor, anti-oxidation, anti-free radical, anti-allergic, anti-bacterialanti-inflammatory and so on. As phenolic hydroxyl groups being active, high polarityand easily oxidized, resveratrol has a short half-life and can not be directly absorbedthrough the cell membrane, leading to a low bioavailability and narrow applications. Soit has important academic and practical value for resveratrol to be chemically modifiedto improve its stability.The resveratrol laurate was successfully synthesized by chemical synthesis methodwith A as the catalyst and resveratrol, lauroylchloride as starting materials. TLC analysisshowed that Rf value of products were0.525and0.613. With a column of C18, acetone-water (55:45) being mobile phase and under isocratic elution, HPLC indicates the peaktime of products are15.487and16.651minutes respectively and the ratio of them is5:1.Using silica gel column chromatography to separate the crude product with hexane-ethyl acetate (5:4) being eluant conditions obtained the products mixture withoutresveratrol. With acetone-water as the mobile phase, under gradient elution conditions,two products were obtained by semi-preparative HPLC. Though FTIR,1HNMR andLC-MS analysis, it indicates that the product named1#and whose melting point isbetween136to170is resveratrol laurate, and the other one named2#and whosemelting point is between85~110℃turned out to be reveratrol dilaurate.The main factors affecting the synthesis of resveratrol laurate is the molar ratio of laurylchloride and reveratrol, reaction time, pH, amount of A. On the basis of single factor experiment, L9(34) orthogonal experiment points out the best conditions for the synthesis of resveratrol laurate are:molar ratio of lauroylchloride and resveratrol being0.8, catalyst addition amount being5%ofresveratrol, the reaction time being4h, and pH value being11.it is calculated the HLB of resveratrol laurate is5.6, under which substance can beabsorbed through the intestinal tract and skin directly.