Method for preparing soybean isoflavone aglycones by catalyzing hydrolysis of soybean isoflavone glycosides via citric acid

A technology of soybean isoflavones and citric acid, applied in the direction of organic chemistry, etc., to achieve the effect of simple operation and low acidity

Inactive Publication Date: 2014-09-24
JILIN INST OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the technical defects of hydrochloric acid catalysis, alkali catalysis and enzyme catalysis in the existing process of converting soybean isoflavones to aglycones, edible citric acid is used to catalyze the hydrolysis process of soybean isoflavones. completely

Method used

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  • Method for preparing soybean isoflavone aglycones by catalyzing hydrolysis of soybean isoflavone glycosides via citric acid
  • Method for preparing soybean isoflavone aglycones by catalyzing hydrolysis of soybean isoflavone glycosides via citric acid
  • Method for preparing soybean isoflavone aglycones by catalyzing hydrolysis of soybean isoflavone glycosides via citric acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Take 50mg of 10.0% soybean isoflavone glycosides into a 50mL round bottom flask, add 2.5mol·L -1 10 mL of citric acid aqueous solution, ultrasonic water bath for 1 hour, ultrasonic frequency 45KHz, water bath temperature 75°C. The reaction solution was transferred to an autoclave, the reaction temperature was 120°C, and the reaction time was 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature.

[0022] A certain amount of the reaction solution was neutralized with saturated sodium carbonate aqueous solution to pH=7, extracted with ethyl acetate, the ester layer was taken, spotted on a silica gel plate, and put in a developing solvent (ethyl acetate: chloroform: methanol = 5:5). :2) Expand in the middle, observe the degree of hydrolysis under ultraviolet light; take another certain amount of reaction solution diluted to 100ppm with methanol, and use HPLC to qualitatively and quantitatively detect the glycoside and aglycon content o...

Embodiment 2

[0024] Take 50mg of 20.5% soy isoflavone glycosides into a 50mL round-bottomed flask, add 2.5mol·L -1 10 mL of citric acid aqueous solution, ultrasonic water bath for 1 hour, ultrasonic frequency 45KHz, water bath temperature 75°C. The reaction liquid was transferred to an autoclave, the reaction temperature was 130° C., and the reaction time was 3.5 hours. After the reaction, the reaction liquid was cooled.

[0025] Other operations are the same as in Example 1. Take a certain amount of the reaction solution and neutralize it with saturated sodium carbonate aqueous solution to pH=7, extract it with ethyl acetate, take the ester layer, spot the sample on the silica gel plate, and put the developing agent (ethyl acetate: Develop in chloroform:methanol=5:5:2) and observe the degree of hydrolysis under ultraviolet light. At the same time, another certain amount of reaction solution was diluted to 100 ppm with methanol, and the content of glycoside and aglycon in the reaction solutio...

Embodiment 3

[0027] Take 50mg of 40.0% soybean isoflavone glycosides and place them in a 50mL round-bottom flask, add 3.5mol·L -1 10ml of citric acid aqueous solution, ultrasonic water bath for 1 hour, ultrasonic frequency 45KHz, water bath temperature 75℃. The reaction liquid was transferred to the autoclave, the reaction temperature was 120° C., and the reaction time was 3 hours. After the reaction, the reaction liquid was cooled.

[0028] Other operations are the same as in Example 1. Take a certain amount of the reaction solution and neutralize it with saturated sodium carbonate aqueous solution to pH=7, extract it with ethyl acetate, take the ester layer, spot the sample on the silica gel plate, and put the developing agent (ethyl acetate: Develop in chloroform:methanol=5:5:2) and observe the degree of hydrolysis under ultraviolet light. At the same time, another certain amount of reaction solution was diluted to 100 ppm with methanol, and the glycoside and aglycon content of the reactio...

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Abstract

The invention discloses a method for preparing soybean isoflavone aglycones by catalyzing hydrolysis of soybean isoflavone glycosides via citric acid. The method uses 10%-92% of glycoside-type soybean isoflavone glycosides as a raw material and edible additive-grade citric acid as a catalyst. At certain temperature and pressure, the soybean isoflavone glycosides in the raw material hydrolyze into soybean isoflavone aglycones. The aglycone hydrolysis rate of the glycosides reaches 100%. The method provided by the invention is simple to operate, even more important, the method uses the edible citric acid as the catalyst, so that the hydrolysis process is green and environment-friendly and the hydrolysis product is directly applied to health-care products and soybean heatlth care products without separation. Therefore, the method provided by the invention solves the problems of equipment corrosion and wastewater pollution in the catalysis process of inorganic acid and bad security of edible products. The method provided by the invention is a practical technique suitable for industrialized production of soybean isoflavone aglycones.

Description

Technical field [0001] The invention relates to a method for preparing soybean isoflavone aglycone by citric acid catalyzed hydrolysis of soybean isoflavone glycoside. Background technique [0002] Soy isoflavones are a secondary metabolite produced during the growth of soybeans and other legumes. Studies have found that sufficient intake of soy isoflavones can effectively reduce the risk of osteoporosis, menopausal syndrome, and hypercholesterolemia. , And the risk of cardiovascular disease and cancer. There are three main components of isoflavones naturally occurring in soybeans, namely genistein, daidzein and glycitein, each of which mainly exists in 4 forms: malonyl Glucoside type, acetyl glucoside type, β-glucoside type and aglycone type (glycon), of which the combined type glycosides account for 80%-95% of the total isoflavone content. Studies have found that soy isoflavones in the form of glycosides cannot be directly absorbed by the wall of the small intestine, and must...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/36
Inventor 于丽颖成乐琴刘治刚徐颖超
Owner JILIN INST OF CHEM TECH
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