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Synthetic method of isoflavone 7-O-glucose glycoside

A technology of glucoside and synthesis method, which is applied in the field of synthesis of isoflavone 7-O-glucoside, can solve the problems of less research, low stereoselectivity, and high synthesis yield, and achieve mild reaction conditions, high synthesis rate, and post-production Handle simple effects

Inactive Publication Date: 2011-06-22
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthesis of glycosides is generally carried out under the action of a glycosyl donor and different acceptors under the action of a catalyst. However, due to the presence of multiple hydroxyl groups in both the isoflavone aglycon and the sugar donor, the regioselectivity of the glycosidation reaction becomes difficult, and at the same time In addition, α and β two isomers can be produced in the glycosidic condensation reaction, and the stereoselectivity of the glycosidic reaction must also be considered. Therefore, the research on the preparation of flavonoid glycosides by the direct condensation of flavonoids or isoflavone aglycones and sugar donors relatively few
From the perspective of literature, the synthesis of isoflavone glycosides usually adopts Koenigs-Knorr method, phase transfer catalysis method or trichloroacetimide, trifluoroacetimide esterification method, relatively speaking, although the stereoselectivity of the first two is relatively high Small, but high synthesis yield

Method used

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  • Synthetic method of isoflavone 7-O-glucose glycoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1) Preparation of isoflavone-7-O-β-D-tetraacetylglucoside

[0021] Dissolve 10mmol of 7-hydroxyisoflavone in 70mL of sodium bicarbonate solution containing an equimolar amount of potassium chloride at a concentration of 1mol L -1 Add 0.32mL of phase transfer catalyst TDA-1, i.e. tris(3,6-dioxaheptyl)amine (1mmol), slowly add 70mL of 5.03g 1-bromo-2,3,4 , 6-O-tetraacetyl-α-D-glucopyranose (12mmol) in dichloromethane solution, first add 50mL and react at 40°C for 4h, then add the remaining 20mL of dichloromethane solution, continue to react at 40°C 2h; After the reaction is over, add 200mL of water and use 1mol·L -1 Sulfuric acid to adjust the pH to neutral, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered off the desiccant, and concentrated under reduced pressure to obtain the crude product; silica gel column separation, V-ethyl acetate: V-petroleum ether=1 : 2 mixed solvent to obtain isoflavone-7-O-β-D-tetraacetylglucoside (5.1 g, 90%) as...

Embodiment 2

[0024] Embodiment 2: the preparation of raw material 7-hydroxyl isoflavone

[0025] 1) Preparation of deoxybenzoin by Friedel-Crafts reaction

[0026] Dissolve 20mmol resorcinol and 20mmol phenylacetic acid in about 20ml freshly distilled boron trifluoride / diethyl ether solution, stir and heat to 70°C, react for 6 hours, cool the reaction solution, add excess ice water, and precipitate After filtration, reflux and dissolve with methanol solution, and decolorize with activated carbon to obtain 4.1 g of white powdery 2,4-dihydroxydeoxybenzoin with a yield of 89%.

[0027] 2) Preparation of 7-hydroxyisoflavones

[0028] Dissolve 15 mmol of the above-prepared deoxybenzoin in a mixed solution of 20 mL of N,N-dimethylformamide and 10 mL of boron trifluoride / diethyl ether, add 6 mL of methylsulfonyl chloride dropwise at 40°C, and heat up to 80°C for 3 hours ; The reactant was poured into crushed ice, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentra...

Embodiment 3

[0029] Embodiment 3: the preparation of raw material 5,7-dihydroxyisoflavone

[0030] 1) Preparation of deoxybenzoin by Hexceles reaction

[0031] Dissolve 20mmol of phloroglucinol, 20mmol of phenylacetonitrile and 3g of anhydrous zinc chloride in 100mL of diethyl ether, pass in dry hydrogen chloride gas at 0°C, stir for 5h, let stand overnight, and continue to pass in hydrogen chloride for 3h. Pour out the upper ether layer, and wash the solid several times with ether, and the obtained imide salt was washed with 0.1mol·L -1 Reflux hydrochloric acid for 3 hours, cool and filter, rinse the filter cake several times with ice water, and recrystallize with 75% methanol to obtain 3.7 g of light yellow powder 2,4,6-trihydroxydeoxybenzoin with a yield of 75%.

[0032] 2) Preparation of 5,7-dihydroxyisoflavones

[0033] Dissolve 15 mmol of the above-prepared deoxybenzoin in a mixed solution of 20 mL of N,N-dimethylformamide and 10 mL of boron trifluoride / diethyl ether, add 6 mL of m...

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Abstract

The invention discloses a method for synthesizing isoflavone 7-O-glucosides, which uses 7-hydroxy isoflavone and a derivative thereof as raw materials and comprises the following steps: 1) the 7-hydroxy isoflavone and the derivative of aglycon are dissolved in a sodium bicarbonate solution of potassium chloride, added with a phase transfer catalyst of tris(dioxa-3,6-heptyl)amine(TDA-1), stirred and added with a methylene dichloride solution of 1-bromo-2,3,4,6-O-tetraacetyl-alpha-D-glucopyranose fractionally, heated for passivation to form 7-O-beta-D-tetraacetylglucose isoflavone and derivatives thereof; 2), the 7-O-beta-D-tetraacetylglucose isoflavone and derivatives thereof are dissolved in methanol, subjected to removal of acetyl under an alkalescent condition and passivated to form the7-O-beta-D-glucose isoflavone and derivatives thereof. The method for preparing the prepared isoflavone 7-O-glucosides has the advantages of high synthesis rate, mild reaction conditions, simple posttreatment, low raw material cost, safety and reliability, and suitability for large-scale industrial production.

Description

【Technical field】 [0001] The invention relates to organic chemistry and functional food synthesis technology, in particular to a synthesis method of isoflavone 7-O-glucoside. 【Background technique】 [0002] Isoflavones with C 6 -C 3 -C 6 It is the basic mother nucleus structure. It is mainly distributed in the Papilionaceae subfamily of Fabaceae in nature, such as soybean, Mexican white bean, alfalfa and mung bean. , estrogen-like and inhibiting the growth of cancer cells and other physiological activities. Isoflavones isolated from soybeans have 12 isomers, 3 of which are in the form of aglycones, namely genistein, daidzein and glycitein, and the remaining 9 are The form of glucoside accounts for about 97-98% of the natural distribution of soybean isoflavones, so the synthesis of isoflavone glycosides has become one of the hot spots that people pay attention to. [0003] The synthesis of glycosides is generally carried out under the action of a glycosyl donor and diffe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/07
Inventor 雷英杰欧阳杰刘福德杨亮陈宝泉
Owner TIANJIN UNIVERSITY OF TECHNOLOGY