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Study On The Synthesis Of4-hydroxy Resveratrol And4-hydroxy Resveratrol Methylation

Posted on:2013-08-22Degree:MasterType:Thesis
Country:ChinaCandidate:W M ChenFull Text:PDF
GTID:2234330395955162Subject:Medicinal chemistry
Abstract/Summary:PDF Full Text Request
Trans-3,4,5,4’-tetrahydroxystilbene is one of polyphenol hydroxystilbene, which has very extensive pharmacological activities,such as antibiosis,pre ventting heart disease,anticancer; combatting platelet aggregation,protecti ngliver,radiation protection, immunomodulation, anti-HIV activity and it also can repairing DNA damage caused by Tcm Prescription which cure SARS.Trans-3,4,5,4’-tetramethoxystilbene is the derivatives of4-hydroxy resv eratrol whose hydroxy is methylated. Its outstanding advantage is its high anti-tumor aciivity,mainly embodied in high bioavailability, high stabilit y,nocross-resistance.This paper use3,4,5-trimethoxybenzoic acid as raw materiais,through the NaBH1reduction of carboxylic acids to produce3,4,5-trimethoxybenzyl alc ohol,3,4,5-trimethoxybenzyl alcohol halogenated by SOCl2to preparation of3,4,5-trimethoxybenzyl chloride,3,4,5-trimethoxybenzyl chloride and anisic aldehyde condensation of Trans-3,4,5,4’-tetramethoxystilbene,that is the methvlation of4-hydroxylresveratrol.Finally,use BBr3demethylatio n to get Trans-3,4,5,4’-tetrahydroxystilbene,that is4-hydroxyresveratrol. Experiments on the reaction steps are carried out in many ways fumble,de termined the final synthetic route.By NMR、Mass spectrometry confirma tory synthesized in a total yield of68.4%.
Keywords/Search Tags:4-hydroxyresveratrol, methylation derivatives, 4-hydroxy Resveratrol Methylation, 3,4,5-trimethoxybenzoic acid, Wittig-Horner reaction, synthesis
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