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Method for synthesizing ellagic acid by utilizing gallic acid derivative

A technology of gallic acid and its derivatives, applied in the direction of organic chemistry, etc., can solve the problems of harsh reaction conditions, difficulty in realizing industrialization, and high requirements for acid-resistant equipment, and achieve the effect of cheap raw materials, easy control, and high yield

Inactive Publication Date: 2019-04-09
贵阳倍隆生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of ellagic acid prepared by this method is about 40%, but the reaction conditions are harsh, the requirements for acid-resistant equipment are high, and the production cost is high, so it is difficult to realize industrialization; in 2013, Yang Xiaoxiao et al. reported [YangX.X., etal.Sci.Technol.Food, 2013, 34:284-288], using the hydrolysis method to prepare ellagic acid, the method mainly uses pomegranate peel powder as raw material, ultrasonically extracts with 60% ethanol, and extracts through petroleum ether After extracting and removing the fat-soluble substances, and then extracting with ethyl acetate, the obtained extract is hydrolyzed by acid hydrolysis to obtain ellagic acid, and the preparation of ellagic acid by this method can reach 32.7%
[0006] It has been reported that the yield of ellagic acid preparation is low, resulting in a price of about 200,000-300,000 yuan per ton

Method used

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  • Method for synthesizing ellagic acid by utilizing gallic acid derivative
  • Method for synthesizing ellagic acid by utilizing gallic acid derivative
  • Method for synthesizing ellagic acid by utilizing gallic acid derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Weigh 50g of methyl gallate, pour it into a dried 500ml three-necked flask, then add 250ml of 25% concentrated ammonia water, stopper the bottle mouth with a bottle stopper, put it in a constant temperature water bath at 50°C, stir for 12h, then pour the reaction solution into into a 1000ml dry three-neck flask, introduce air, and oxidize for 24 hours. After the reaction is over, filter the reaction solution, dissolve the filter cake with 25% NaOH solution, put in 250 g of activated carbon, stir and decolorize at 25 ° C, filter, and extract the filtrate three times with dichloromethane, separate the filtrate, and adjust the water phase with 25% hydrochloric acid The pH of the extract was 2, crystallized, filtered and dried to obtain light yellow ellagic acid amorphous powder with a yield of 72%.

Embodiment 2

[0022] Weigh 50g of ethyl gallate, pour it into a dried 500ml three-necked flask, then add 250ml of 25% concentrated ammonia water, stopper the bottle mouth, put it in a constant temperature water bath at 50°C and stir for 12h, then pour the reaction solution into Into a 1000ml dry three-necked flask, put 100g of potassium persulfate into it, and react for 5h. After the reaction is over, filter the reaction solution, dissolve the filter cake with 15% NaOH solution, put in 250 g of activated carbon, decolorize and refine at 30°C, filter, and extract the filtrate three times with ethyl acetate, separate the filtrate, and adjust the water phase with 15% hydrochloric acid. The pH of the extract was 1.5, crystallized, filtered and dried to obtain light yellow ellagic acid amorphous powder with a yield of 81%.

Embodiment 3

[0024] Weigh 50g of propyl gallate, pour it into a dried 500ml wide-mouth bottle, then add 250ml of 25% concentrated ammonia water, stopper the bottle mouth, put it in a constant temperature water bath at 50°C and stir for 12h, then pour the reaction solution into Put it into a 1000ml dry three-neck flask, put in m-CPBA60g, and react for 10h. After the reaction is over, filter the reaction solution, dissolve the filter cake with 10% NaOH solution, put in 250 g of activated carbon, stir and decolorize at 35°C, filter, and extract the filtrate three times with dichloromethane, separate the filtrate, and adjust the extract with 10% hydrochloric acid. When the pH is 2, crystallize, filter and dry to obtain light yellow ellagic acid. Its yield was 84%.

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Abstract

The invention discloses a method for synthesizing ellagic acid by utilizing a gallic acid derivative. A technical route comprises the following steps: carrying out ammoniation on the gallic acid derivative and 10 to 25 percent NH3.H2O in a water-bath pot at 45 to 55 DE G C for 5 to 24h; then adding an oxidant into an ammoniation solution and carrying out oxidization reaction for 5 to 24h; after the reaction is finished, filtering a reaction solution and dissolving a filter cake with an NaOH water solution; extracting an alkaline solution with an organic solvent and regulating the pH (Potentialof Hydrogen) of a water phase to be 1.0 to 2.5 by utilizing an HCl solution; carrying out crystallization and filtering; and drying in vacuum to obtain the light-yellow ellagic acid. The method has the advantages of cheap raw materials, moderate reaction temperature, safe reaction process and easiness for controlling; the yield ratio is higher than the reported yield and can reach 70 percent or more; and the ellagic acid synthesized by the method has a light-yellow color and the purity can reach 98 percent or more.

Description

technical field [0001] The invention relates to a preparation method for synthesizing ellagic acid by using gallic acid derivatives. The preparation process of the method is safe and reliable, the operation process is simple, the yield is high, and the color of the product is good. Background technique [0002] Ellagic acid (Ellagic acid, chemical name: 2,3,7,8-tetrahydroxy-[1]-benzopyrano[5,4,3-cde]benzopyran-5,10-dione, English name: 2, 3, 7, 8-tetrahydroxy-benzo-pyrano [5, 4, 3-cde] benzopyran-5, 10-dione). It is a light yellow amorphous powder, insoluble in water, ether, and alcohol, but soluble in alkali, pyridine, and DMSO, and its melting point is greater than 360°C. Ellagic acid is a polyphenolic compound that exists in condensed form (such as ellagitannin) in nature, and FeCl 3 The reaction is blue, when encountering H 2 SO 4 It is yellow. It widely exists in various soft fruits, nuts and other plant tissues, such as tropical fruits, raspberries, pomegranates, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/06
CPCC07D493/06
Inventor 罗志军冯兵张勇民
Owner 贵阳倍隆生物科技有限公司