Synthesis Of A Functional Food Ingredient-Resveratrol

Resveratrol(trans-3,4',5-trihydroxystilbene), found in grapes, peanut, mulberries, and other plants, is a natural phytoalexin biosynthesized in response to pathogenic attack or other stress conditions. In recent times, it has been intensively studied for a variety of biological properties, such as antioxidant activity, inhibition of platelet aggregation, preventive activities against heart diseases and cancer chemo-preventive activity, etc. It can be applies in pharmacy, food and cosmetic, etc. Though it has such wide applications, there is not an inexpensive source for it. So, in order to reduce the producing cost, we studied the methods of chemically synthesizing resveratrol.We had synthesized resveratrol using Wittig and Wittig-Horner reaction and found that Wittig-Horner reaction has evident superiority than Wittig reaction in synthesis of resveratrol. In the dissertation, resveratrol was synthesized in good yield from 4-methoxybenzyl alcohol by bromination, and reaction with triethyl phosphate to give diethyl-(4-methoxybenzyl)phosphonate which was condensed with trans-3,5-dimethoxybenzaldehyde to give trans-3,4',5-trimethoxystilbene, and then demethylation.Wittig-Horner reaction has evident superiority in synthesis of trans-3,4',5-trimethoxystilbene due to its mild reaction conditions, simple manipulation, high purity and yield of the products in single isomer. Demethylation was performed by treatment with anhydrous aluminum chloride and pyridine with same evident superiority. And the mechanism of the demethylation had been studied. The synthesis of resveratrol was completed with a good overall yield(41.1%).