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Study On The Synthesis Of Resveratrol

Posted on:2020-09-29Degree:MasterType:Thesis
Country:ChinaCandidate:C F JiangFull Text:PDF
GTID:2381330575994592Subject:Pharmaceutical engineering
Abstract/Summary:PDF Full Text Request
1.Synthesis of resveratrol(4-Hydroxyphenyl)-vinyl-1,3-benzenediol(simplified resveratrol)is a polyphenohc compound.In recent years,it has developed very well in the fields of cosmetics,food,medicine,health care products because of its anti-oxidation,strengthening blood vessel wall,promoting digestion of the stomach,reducing blood fat,increasing body resistance,and resisting radiation.Plant polyphenols exist in a variety of plants and have high medical value,and have been well applied in the field of traditional Chinese medicine.Resveratrol is the most widely used among many polyphenolic compounds.It not only has a very high medicinal value,but also is highly sought after in the beauty and skin care industry for its anti-aging effect.There are two main ways to synthesize resveratrol,the first is bio-extraction and the second is chemical synthesis.Based on the traditional resveratrol synthesis process,this paper explored a new process and optimized the process.The first part of this paper is based on p-methoxycinnamaldehyde and then subjected to aldol condensation,cyclization,hydrolysis,decarboxylation,dehydrogenation reduction and deprotection to obtain the final product resveratrol.The second part is to screen out the appropriate protecting groups based on the first part,and finally determine the use of benzyl as a protecting group to synthesize resveratrol.The traditional method of synthesizing resveratrol is particularly important for the protection of phenolic hydroxyl groups.This is because resveratrol contains three phenolic hydroxyl groups,which are prone to deterioration and indirectly cause a large amount of waste water to be produced during the deprotection process.So we constructed the aromatic ring by itself to synthesize the bare phenolic hydroxyl group.In the first process,we used methyl as a protective group.This route has mild reaction conditions,and the reaction yields of the first few steps are high.However,in the demethylation reaction,the conventional deprotection reagent is inferior.BBr3 has a desirable effect,but is not suitable for industrialization.On this basis,we used the second process route,which screened the ester group,tert-butyl group,dihydropyranyl group and benzyl group as protective groups,and found that the benzyl group had the best effect.In the dehydrogenation and deprotection process,the two-step reaction can be completed together.Thereby,the production of industrial wastewater is greatly reduced,the industrial cost is reduced,and it is very suitable for industrial industrialization.2.Synthesis process of epoxy resin compoundsOne common feature of epoxy compounds in their molecular formula is the inclusion of two or more epoxy groups,which makes them widely used in composite materials,coatings,adhesives and other fields.The epoxy group in its molecular formula gives it good heat resistance,light resistance and corrosion resistance.The epoxy resin compounds synthesized herein mainly include two types of glycidylamines and glycidyl esters.The synthesis method is an open-loop and closed-loop two-step method,and then the process optimization is performed for each step reaction so that it can be used for industrial large-scale production.In this paper,the main method of testing the experimental results is nuclear magnetic resonance hydrogen spectroscopy(NMR-H),supplemented by liquid chromatography-mass spectrometry(LC-MS).Through the comparison of the advantages and disadvantages of the two synthetic routes of resveratrol,comprehensive consideration of industrial production conditions,and finally selected a route that can be industrialized.
Keywords/Search Tags:resveratrol, polyphenols, protecting group, medicine, process optimization
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