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Synthesis process of neohesperidin

A new hesperidin and synthetic process technology, applied in the direction of organic chemistry, chemical instruments and methods, sugar derivatives, etc., can solve the problems of difficult separation of catalysts and solvents, inability to purify intermediate products, and low product quality, so as to achieve the goal of protecting Vascular system, short reaction time, high purity effect

Inactive Publication Date: 2017-09-01
HUNAN XINLI BIOLOGICAL SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The purpose of the present invention is to solve the problems in the prior art that the intermediate product cannot be purified, the catalyst and the solvent are difficult to separate, the product quality is not high, and it is easy to cause harm to workers.

Method used

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  • Synthesis process of neohesperidin
  • Synthesis process of neohesperidin
  • Synthesis process of neohesperidin

Examples

Experimental program
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Effect test

Embodiment 1

[0055] A kind of synthetic technique of neohesperidin, is characterized in that, comprises the following steps:

[0056] 1) Preparation of root bark acetophenone-4′-β-neohesperidoside

[0057] After adding 8g of naringin into the reactor, add 96mL of potassium hydroxide solution with a mass fraction of 17.5% in the reactor; feed nitrogen into the reactor to drive out the air in the reactor, and then heat to 100 ℃, obtained mixture A after reflux reaction for 2h;

[0058] 2) Purification of root bark acetophenone-4′-β-neohesperidoside

[0059] 2.1) Put the mixture A in an ice bath, adjust the pH of the mixture A to 6±0.5 with concentrated hydrochloric acid, precipitate a light yellow crystal, heat above 70°C until the crystals are completely dissolved, and obtain the mixture B;

[0060] The concentration range of the concentrated hydrochloric acid is 36%.

[0061] 2.2) Let the mixture B stand at room temperature for 2 hours, crystallize after cooling, filter under reduced pr...

Embodiment 2

[0077] A kind of synthetic technique of neohesperidin, is characterized in that, comprises the following steps:

[0078] 1) Preparation of root bark acetophenone-4′-β-neohesperidoside

[0079] After adding 8g of naringin into the reactor, add 64mL of potassium hydroxide solution with a mass fraction of 20% in the reactor; feed nitrogen into the reactor to drive out the air in the reactor, and then heat to 100 ℃, obtained mixture A after reflux reaction for 2h;

[0080] 2) Purification of root bark acetophenone-4′-β-neohesperidoside

[0081] 2.1) Put the mixture A in an ice bath, adjust the pH of the mixture A to 6±0.5 with concentrated hydrochloric acid, precipitate a light yellow crystal, heat above 70°C until the crystals are completely dissolved, and obtain the mixture B;

[0082] The concentration range of the concentrated hydrochloric acid is 37%.

[0083] 2.2) Let the mixture B stand at room temperature for 3 hours, crystallize after cooling, filter under reduced pres...

Embodiment 3

[0099] A kind of synthetic technique of neohesperidin, is characterized in that, comprises the following steps:

[0100] 1) Preparation of root bark acetophenone-4′-β-neohesperidoside

[0101] After adding 8g of naringin into the reactor, add 96mL of potassium hydroxide solution with a mass fraction of 22.5% in the reactor; feed nitrogen into the reactor to drive out the air in the reactor, and then heat to 100 °C, the mixture A was obtained after reflux reaction for 1.5h;

[0102] 2) Purification of root bark acetophenone-4′-β-neohesperidoside

[0103] 2.1) Put the mixture A in an ice bath, adjust the pH of the mixture A to 6±0.5 with concentrated hydrochloric acid, precipitate a light yellow crystal, heat above 70°C until the crystals are completely dissolved, and obtain the mixture B;

[0104] The concentration range of the concentrated hydrochloric acid is 38%.

[0105] 2.2) Let the mixture B stand at room temperature for 4 hours, crystallize after cooling, filter under...

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Abstract

The invention discloses a synthesis process of neohesperidin. The synthesis process is characterized by comprising the following steps: 1) preparing phloroacetophenone-4'-beta-neohesperidoside; 2) purifying the phloroacetophenone-4'-beta-neohesperidoside; 3) preparing neohesperidin. The invention provides a neohesperidin synthesis process which has the following advantages: solvent and catalyst can be repeatedly used; yield is high; separation and purification of the intermediate product phloroacetophenone-4'-beta-neohesperidoside and neohesperidin are easy; and cost is low. In the aspect of biological activity, the product neohesperidin shows a wide pharmacologic action such as anti-bacteria, anti-inflammation, protection of the cardiovascular system, immunoregulation and the like. In addition, the product is an important raw material for synthesis of a sweetener neohesperidin dihydrochalcone.

Description

technical field [0001] The present invention relates to a synthesis process of a plant raw material drug, in particular to a method for synthesizing another more important plant raw material drug neohesperidin by using a plant raw material drug naringin as a basic raw material. Background technique [0002] The southern provinces of my country produce millions of tons of citrus and pomelo every year, and pomelo and orange peel resources are very rich. However, only a small amount is used for traditional Chinese medicine as medicine, and most of them are discarded by people, resulting in a huge waste of resources. The content of neohesperidin in plants is far less than that of naringin, so using naringin extracted from pomelo peel and orange peel as a raw material to synthesize neohesperidin has broad development prospects. [0003] Neohesperidin is a dihydroflavonoid compound, which is a flavone glycoside formed by hesperetin and rutinose, and its molecular formula is C 28 ...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00C07H1/06
CPCC07H17/07C07H1/00C07H1/06
Inventor 王芳周志明周小华陈尧辉冉程王鹏付微婷孙万万
Owner HUNAN XINLI BIOLOGICAL SCI & TECH
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