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Process for synthesizing natural active product dihydroquercetin

A technology that uses acidic conditions and phenolic hydroxyl to form ether, which is applied in the direction of organic chemistry, etc., can solve the problems of affecting the extraction and utilization of active ingredients, many by-products, and many reaction steps, and achieves green production procedures, great economic and social benefits. , the effect of simple equipment

Active Publication Date: 2014-06-18
ZHANG JIA GANG VINSCE BIO PHARM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Five-step reaction, the final total molar yield is less than 10%, and dangerous chemicals such as NaH are used at the same time, the atom economy is low, there are many by-products, it is difficult to separate and handle, and it is not suitable for industrial production
[0007] The above method has the following disadvantages in the preparation of (2R, 3R)-dihydroquercetin: (1) The disadvantage of natural extraction is that the resource utilization rate is low. After dihydroquercetin is extracted, the extraction and utilization of other active ingredients are affected. , causing the cost to be too high; at the same time, column chromatography and a large amount of water are used in the extraction and separation process, which leads to high energy consumption and large pollution, and it is difficult to obtain high-purity and high-content dihydroquercetin
(2) The disadvantage of using catechin as the starting material to synthesize dihydroquercetin is that the reaction requirements are strict and the yield is extremely low, resulting in many by-products, large environmental pollution, and uneconomical
(3) The disadvantage of the total synthesis of 2,4,6-trihydroxy-acetophenone and 3,4-dihydroxybenzaldehyde as raw materials is that there are many reaction steps, and the final total molar yield is less than 10%. Hazardous chemicals such as NaH have low atom economy and many by-products, which are difficult to separate and handle, and are not suitable for industrialized production

Method used

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  • Process for synthesizing natural active product dihydroquercetin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 Synthesis of 1-caffeoyl-2,4,6-trihydroxyphenol

[0020] In a 500 L enamel reaction kettle, add 200 L of dichloromethane and 40.0 kg of caffeic acid chloride as the reaction raw material, cool the jacket to about 5°C, add 13.5 kg of anhydrous aluminum trichloride in batches, and control the temperature at 5-10 °C, stirred for 2 h to form a complex. Continue to control the temperature within 10 °C, add 26.0 kg of raw material phloroglucinol in batches, and slowly rise to room temperature, and then stir for 4 h. The complete reaction of caffeic acid chloride is monitored by thin layer chromatography, and the acylation reaction is considered complete. Cool down to within 10 °C, slowly add 5% sodium hydroxide solution to about pH 9, and hydrolyze for 0.5 h. Then adjust the pH value to 6-7 with 5% dilute hydrochloric acid, and let it stand for stratification. After the organic phase was separated, it was extracted once with 100 L of dichloromethane, the organic ph...

Embodiment 2

[0021] Example 2 Synthesis of 1-(3,4-dihydroxy)-phenyl, 2-(2,4,6-trihydroxy)phenyl-oxirane

[0022] In a 500 L enamel reaction kettle, add 55.0 kg of 1-caffeoyl-2,4,6-trihydroxyphenol and stir to dissolve with 300 L of methanol, cool down the jacket to about 5°C, and add 40.0 kg of m-chloroperoxybenzoic acid in batches. kg, and the temperature was controlled at 15 °C, and the reaction was stirred for 4 h. The raw material 1-caffeoyl-2,4,6-trihydroxyphenol basically disappeared as monitored by thin-layer chromatography, and the oxidation reaction was considered complete. Cool down to within 10 °C, slowly add 12.5 L of saturated sodium bisulfite solution to remove peroxy-m-chloroperoxybenzoic acid, concentrate under reduced pressure, and recover methanol. Add 150 L of water and 200 L of dichloromethane to extract twice, combine the organic phases, dry, and concentrate under reduced pressure to obtain 1-(3,4-dihydroxy)-phenyl, 2-(2,4,6-tri Hydroxy) phenyl-oxirane intermediate cr...

Embodiment 3

[0023] The synthesis of embodiment 3 dihydroquercetin

[0024]In a 500 L enamel reaction kettle, add 200 L of dichloromethane and dry 1-(3,4-dihydroxy)-phenyl, 2-(2,4,6-trihydroxy)phenyl-epoxy After stirring and dissolving 50.0 kg of ethane intermediate, the temperature of the jacket was lowered to about 5 °C, and the acid catalyst was slowly strengthened with 10.0 L of trifluoroacetic acid, and the temperature was controlled at 0-5 °C, and the reaction was stirred for 5 h. Thin-layer chromatography monitors the complete reaction of the raw material intermediate, which is considered as the completion of the ether-forming reaction. Adjust the pH value to 6-7 with saturated sodium bicarbonate solution, and let stand to separate layers. After the organic phase was separated, it was extracted once with 100 L of dichloromethane, the organic phases were combined, dried, concentrated under reduced pressure, and dried to obtain 45.8 kg of crude dihydroquercetin. The crude product wa...

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Abstract

The invention discloses a process for synthesizing (2R,3R)-dihydroquercetin. The process comprises the specific steps of carrying out Friedel-Crafts acylation on caffeic acyl chloride and phloroglucin which serve as raw materials, forming epoxy bonds through peroxidizing double bonds, opening cycles under acidic conditions, forming ether with phenolic hydroxyl, and carrying out separation, purification and crystallization after reaction is ended, thereby obtaining the product with high content and high purity. In the aspects of reagents and raw and auxiliary materials used during the reaction, both environment-friendliness and efficiency are taken into account. The process disclosed by the invention has the advantages of high atom economical efficiency, simple equipment and environment-friendly production procedure and has very large economic and social benefits.

Description

technical field [0001] The invention relates to the synthesis of a natural active ingredient (2R, 3R)-dihydroquercetin, in particular to the synthesis of caffeic acid chloride and phloroglucinol as raw materials, and to the reactions including Fuke acylation, double bond peroxidation to form a ring Oxygen bond, ring-opening under acidic conditions and phenolic hydroxyl to form ether, separation and purification to obtain (2R,3R)-dihydroquercetin. Background technique [0002] The chemical name of Dihydroquercetin is (2R,3R)-3,3',4',5,7-pentahydroxy-dihydroflavone, also known as Taxifolin, Taxifolin and Taxifolin. Dihydroquercetin has a wide range of biological activities, can affect fat metabolism by regulating the activity of enzymes, has a strong inhibitory effect on the growth of malignant lymphocytes and leukemia cells, and has a strong inhibitory effect on Staphylococcus aureus, Escherichia coli, Shigella and typhoid It has a strong antibacterial effect, and also has a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32
CPCC07D311/32
Inventor 彭学东张梅赵金召闫勇义
Owner ZHANG JIA GANG VINSCE BIO PHARM
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