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Synthesis technology of active natural product dihydromyricetin

A technology of complexes and acidic conditions, applied in the direction of organic chemistry, can solve problems affecting the extraction and utilization of active ingredients, low resource utilization, and large pollution, and achieve green production procedures, large economic and social benefits, and equipment simple effect

Inactive Publication Date: 2014-05-28
ZHANG JIA GANG VINSCE BIO PHARM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above method has the following disadvantages in the preparation of (2R, 3R)-dihydromyricetin: (1) The natural extraction has the disadvantage of low resource utilization rate. After dihydromyricetin is extracted, it will affect the extraction and utilization of other active ingredients, resulting in the cost is too high
(2) At the same time, a large amount of solvents such as water and ethanol are used in the extraction and separation process, resulting in high energy consumption and heavy pollution, making it difficult to obtain high-purity and high-content dihydromyricetin
(3) Dihydromyricetin is semi-synthesized using myricetin as a raw material. The raw material myricetin still needs to be extracted from nature, which costs more and produces by-products that are difficult to separate and process, which is not suitable for large-scale industrial production

Method used

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  • Synthesis technology of active natural product dihydromyricetin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1 Synthesis of 2-(3,4,5-trihydroxy)-phenylacrylic acid acyl-1,3,5-trihydroxyphenol

[0017] In a 500 L enamel reaction kettle, add 200 L of tetrahydrofuran and 40.0 kg of reaction raw material 3,4,5-trihydroxy-phenylacrylic acid chloride, cool the jacket to about 5°C, and add 12.0 kg of anhydrous aluminum trichloride in batches, And control the temperature at 5-10 ℃, stir the reaction for 2 h to form a complex. Continue to control the temperature within 10 °C, add 25.5 kg of raw material phloroglucinol in batches, and slowly rise to room temperature, then stir for 4 h, and monitor the completeness of the raw material 3,4,5-trihydroxy-phenylacrylic acid chloride by thin layer chromatography. reaction, the acylation reaction was 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 concentrate to remove tetrahydrofuran. ...

Embodiment 2

[0018] Example 2 Synthesis of 1-(3,4,5-trihydroxy)-phenyl, 2-(2,4,6-trihydroxy)phenyl-oxirane

[0019] In a 500 L enamel reaction kettle, add 53.0 kg of 2-(3,4,5-trihydroxy)-phenylacrylic acid acyl-1,3,5-trihydroxyphenol, stir and dissolve with 300 L of ethanol, and cool the jacket to 5°C About 40.0 kg of m-chloroperoxybenzoic acid was added in batches, and the temperature was controlled at 15 °C. The reaction was stirred for 4 h, and the raw material 2-(3,4,5-trihydroxy)-phenylacrylic acid acyl-1 was monitored by thin-layer chromatography. , 3,5-trihydroxyphenol basically disappeared, 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-dih...

Embodiment 3

[0020] The synthesis of embodiment 3 dihydromyricetin

[0021] In a 500 L enamel reaction kettle, add 200 L THF and dry 1-(3,4,5-trihydroxy)-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 concentrate to remove tetrahydrofuran. Then extracted twice with 100 L of dichloromethane, combined the organic phases, dried, concentrated under reduced pressure, and dried to obtain 45.8 kg of crude dihydromyricetin. The crude product was dissolved in 230 L of absolute ethanol, finely...

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Abstract

The invention relates to a synthesis technology of (2R, 3R)-dihydromyricetin, comprising the following steps: taking 3,4,5-trihydroxy-phenylacryl chloride and phloroglucinol as raw materials; carrying out Friedel-Crafts acylation; peroxiding a double bond into an epoxy bond; opening a loop under an acidic condition and forming ether with a phenolic hydroxyl group; carrying out separation, purification and crystallization at the end of the reaction to obtain products with high content and high purity. Green environmental protection and efficiency are considered in the both aspects of reaction reagents and raw and auxiliary materials. The method provided by the invention has advantages of high atom economic type, simple equipments, green and environmental production procedure, and has great economic and social benefits.

Description

technical field [0001] The present invention relates to a kind of synthesis of natural active ingredient (2R, 3R)-dihydromyricetin, be specifically related to synthetic raw material is 3,4,5-trihydroxyl-benzeneacrylic acid chloride and phloroglucinol, involves reaction including The double bond is peroxidized into an epoxy bond, and the ring is opened under acidic conditions to form an ether with the phenolic hydroxyl group, and (2R,3R)-dihydromyricetin is obtained by separation and purification. Background technique [0002] Dihydromyricetin, the chemical name is (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-4-one, also known as Dihydromyricetin, fukien tea, albino, dihydromyricetin, dihydromyricetin, staphylococcin. Dihydromyricetin has a wide range of biological activities, scavenging free radicals, anti-oxidation, anti-thrombosis, anti-tumor, anti-inflammatory and many other unique effects. In addition, dihydromyricetin is a special kind of flavonoids. In ...

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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