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Method for preparing andrographolide-19-sulfate-16-sodium carboxylate

A technology of andrographolide and sulfate ester, applied in the direction of preparation of sulfate ester, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of poor solubility and stability, etc.

Pending Publication Date: 2021-05-11
JIANGZI QINGFENG PHARMACEUTICALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally, after extracting andrographolide, it is prepared into injections of various water-soluble derivatives, such as adding sulfuric acid with sodium sulfite or adding reaction with sodium bisulfite, to obtain water-soluble sulfonate, sodium bisulfite andrographolide (Lianbizhi Injection), monopotassium succinate half ester, refined from andrographolide through esterification, dehydration, and salt formation 14-dehydroxyl-11,12-didehydroandrographolide-3,19- Potassium disuccinate half ester sodium salt (Yanhuning injection) or 14-dehydroxy-11,12-didehydroandrographolide-3,19-disuccinate half ester monopotassium salt, but the above salts are in water Solubility and stability are not particularly good

Method used

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  • Method for preparing andrographolide-19-sulfate-16-sodium carboxylate
  • Method for preparing andrographolide-19-sulfate-16-sodium carboxylate
  • Method for preparing andrographolide-19-sulfate-16-sodium carboxylate

Examples

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Embodiment 1

[0023] 1) Preparation of total sulfonated andrographolide: take absolute ethanol and place it in a reaction vessel, add 200ml of concentrated sulfuric acid with a chemically pure specific gravity of 1.84 on a cold water bath, add 100g of andrographolide powder, stir well, and place at 40°C Stir the reaction at ±2°C for 25 hours, add ethanol and stir evenly, control the temperature on a cold water bath at 40°C±2°C, neutralize with sodium hydroxide until the pH value is 7.0; then add ethanol, stir well, and let stand for 2 hours Filter and concentrate the filtrate to obtain the total sulfonate of andrographolide.

[0024] 2) Resin column purification of polystyrene-divinylbenzene type: take the total sulfonated andrographolide obtained in step 1), dissolve it in water and load it on the macroporous resin column D-101, and then use water and different concentrations of ethanol (5% ~60%) for elution, and the eluted fractions with 5%~10% ethanol were combined.

[0025] 3) Purifica...

Embodiment 2

[0039]1) Preparation of total sulfonated andrographolide: take absolute ethanol and place it in a reaction vessel, add 300ml of concentrated sulfuric acid with a chemically pure specific gravity of 1.84 on a cold water bath, add 100g of andrographolide powder, stir well, and place at 40°C Stir and react at ±2°C for 20 hours, add ethanol and stir evenly, control the temperature on a cold water bath at 40°C±2°C, neutralize with sodium hydroxide until the pH value is 6.5; then add ethanol, stir well, and let stand for 2 hours Filter and concentrate the filtrate to obtain the total sulfonate of andrographolide.

[0040] 2) Resin column purification of polystyrene-divinylbenzene type: take the total sulfonated andrographolide obtained in step 1), dissolve it in water and load it on the macroporous resin column D-101, and then use water and different concentrations of ethanol (5% ~60%) for elution, and the eluted fractions with 5%~10% ethanol were combined.

[0041] 3) Purification...

Embodiment 3

[0044] 1) Preparation of total sulfonated andrographolide: take absolute ethanol and place it in a reaction vessel, add 500ml of concentrated sulfuric acid with a chemically pure specific gravity of 1.84 on a cold water bath, add 100g of andrographolide powder, stir well, and place at 40°C Stir and react at ±2°C for 30 hours, add ethanol and stir evenly, control the temperature on a cold water bath at 40°C±2°C, neutralize with sodium hydroxide until the pH value is 7.5; then add ethanol, stir well, and let stand for 2 hours Filter and concentrate the filtrate to obtain the total sulfonate of andrographolide.

[0045] 2) Resin column purification of polystyrene-divinylbenzene type: take the total sulfonated andrographolide obtained in step 1), dissolve it in water and load it on the macroporous resin column D-101, and then use water, different concentrations of ethanol (5% ~60%) for elution, and the eluted fractions with 5%~10% ethanol were combined.

[0046] 3) Purification o...

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Abstract

The invention discloses a preparation method of andrographolide-19-sulfata-16-sodium carboxylate. The method comprises the following steps: carrying out hydrolysis and sulfonation reaction on andrographolide and sulfuric acid, carrying out neutralization reaction on the andrographolide and a sodium-containing alkaline solution to generate a total sulfonated substance, dissolving the total sulfonated substance in water, loading the dissolved total sulfonated substance to a polystyrene-divinylbenzene type resin column, sequentially eluting with water and ethanol with different concentrations, combining ethanol elution fractions, then passing through a reverse-phase C18 bonded silica gel column, sequentially eluting with water and ethanol with different concentrations, combining ethanol elution fractions, concentrating, and recrystallizing. The method greatly improves the sulfonation yield, and has the characteristics of mild conditions, simple post-treatment, high product purity, low production cost and simple and convenient process.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to the synthesis, separation and purification method of andrographolide-19-sulfate-16-sodium carboxylate. Background technique [0002] Andrographolide is a diterpenoid compound in Andrographis paniculata (Burm.f.) Nees, molecular formula: C 20 h 30 o 5 , is colorless prismatic or rectangular crystal, m.p.230~232℃, [α] D -112.7° (C, 0.53, MeOH). Very bitter taste, soluble in methanol, ethanol, propanol, pyridine, slightly soluble in chloroform, ether, hardly soluble in water and petroleum ether. Because andrographolide is insoluble in water, it brings difficulties to the preparation of liquid preparations. At present, various methods are used to convert andrographolide into various derivatives to improve the water solubility of andrographolide. Generally, after extracting andrographolide, it is prepared into injections of various water-soluble derivatives, such as adding sulfur...

Claims

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Application Information

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IPC IPC(8): C07C303/24C07C303/44C07C305/16
CPCC07C303/24C07C303/44C07C2602/28C07C305/16
Inventor 邓双炳张毅刘地发黄冰峰方礼周舟刘佳佳古丽萍刘芳芳刘明颖
Owner JIANGZI QINGFENG PHARMACEUTICALS INC