The Synthesis And Bitter Inhibition Study Of Ferulic Acid And Its Derivative

Bitterness is a formation of animal’s self-protection mechanism in the long evolutionaryprocess, it is one of the most difficult sense of taste for people to accept,a lot of food wasrejected by consumers for its bitter taste. But many bitter substances have pharmacologicalfunction,they are very useful for the human body. Therefore,how to use new technology toremove the bitter taste in the food and medicine, but retain its functional properties,causinggreat interest of many researchers.The synthesis and characterization research of the newbitterness inhibitor named3-[4-(1-carboxyethoxy)-3-methoxyphenyl]-2-propen-oic acid wasstudied in this paper.In this thesis,vanillin and malonic acid as raw materials,using the Knoevenagelcondensation reaction,we successed to get ferulic acid,we investigated the influence of theamount of catalyst,reaction time,the molar ratio of the material and the dosage of solvent onthe yield of ferulic acid,and we perform the orthogonal experiment on the basis of the singlefactor experiments,the optimum conditions of the ferulic acid’s synthetization:Solvent useratio V(benzene):V(DMF)=2:1,the molar ratio of material n(vanillin):n(malonicacid)=1:1.3,catalyst is used in an amount of6%of mass of vanillin,and the reaction time is4h.By optimizing the test, the yield of ferulic acid is70.96%.Using ferulic acid and2-chloro-propionic acid as raw materials and Williamson reactionmethod in alkaline conditions,we successed to get the synthesis named3-[4-（1-carboxyethox）-3-methoxyphenyl]-2-propenoic acid,we investigated the influence of theamount of alkali,reaction time,the molar ratio of material and reaction tempera-ture on yieldof3-[4-(1-carboxyethoxy)-3-methoxyphenyl]-2-propenoic acid,and we perform theorthogonal experiment on the basis of the single factor experiments rate effects and the singlefactor experiment orthogonal experiments,the optimum conditions of3-[4-(1-carboxyethoxy)-3-methoxyphenyl]-2-propenoic acid’s aynthetization:Material molarratio n(ferulic acid):n(2-chloro-propionic acid)=1:1.2,the amount of the alkali is3g,thereaction time is4h,the reaction temperature is90℃.By optimizin-g the test,the yield of3-[4-(1-carboxyethoxy)-3-methoxyphenyl]-2-propenoic acid is60.02%.We investigated the inhibitory effect of3-[4-(1-carboxyethoxy)-3-methoxypheny-l]-2-propenoic acid on saccharin,quinine hydrochloride,stevioside,chlorine potassium andcoffee in bitterness sensory inhibition experiment.We found that the inhibitory effect of3-[4-(1-carboxyethoxy)-3-methoxyphenyl]-2-propenoic acid on bitter taste of potassium chloride and coffee is poor,but the inhibitory effect of3-[4-1-carboxyetheth-oxy)-3-methoxyphenyl]-2-propenoic acid on bitter taste of saccharin,stevioside quininehydrochloride is good,the effect descending order: stevioside>saccharin>quininehydrochloride.With the concentration of3-[4-(1-carboxyethoxy)-3-methoxyphenyl]-2-propenoic acid increased, the bitter substances intensity decreased.The experiment alsocompared the effect between concentrationand ferulic acid, we found that concen-tration3-[4-(1-carboxyethoxy)-3-methoxyphenyl]-2-propenoic acid has the better effect, but theeffect on potassium chloride and coffee is not very obvious.