Synthesis process of phloroacetophenone-4'-beta-neohesperidoside

A technology of root bark acetophenone and neohesperidoside, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the instability of glycosides and flavonoid rings, and the large difference between product yield and theoretical yield , glycoside and flavonoid ring damage, etc., to achieve the effects of inhibiting side reactions, low cost, and small environmental pollution

Inactive Publication Date: 2017-12-22
XIANGXI HUALI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In summary, the current preparation of neohesperidoside uses an aqueous solution of an inorganic strong base as the reaction system, and uses high-temperature reflux to hydrolyze naringin. Since the raw material for the preparation of root bark acetophenone-4′-β-neeohesperidoside It is naringin. Under high temperature conditions, the glucoside and flavonoid rings in the naringin structure are extremely unstable in alkaline water. When the above method is used to hydrolyze naringin, the glycoside and flavone rings in naringin are also At the same time, it is destroyed, resulting in a large difference between the product yield and the theoretical yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A preparation method of root bark acetophenone-4'-β-neohesperidoside, comprising the steps of:

[0028] (1) Add 100 grams of 60% ethanol and 20 grams of sodium ethylate in the reaction flask to be mixed with an organic alkali-alcohol mixed solution;

[0029] (2) Add 24 grams of naringin into the prepared sodium ethoxide ethanol solution, heat up to 85°C, and react for 2 hours;

[0030] (3) Cool the reaction solution to 35°C, slowly add hydrochloric acid to adjust the pH to 6.5-7.0;

[0031] (4) the reaction solution obtained in step (3) is concentrated to the system without alcohol, and then diluted with 100 grams of water;

[0032] (5) Reduce the reaction system of step (4) to 25° C., filter, wash the filter cake with 50 grams of water, and vacuum-dry the filter cake at 60° C. for 16 hours to obtain 15.84 grams of off-white powdery solid, with a weight yield of 66% and a content of 98.3%. .

Embodiment 2

[0034] A preparation method of root bark acetophenone-4'-β-neohesperidoside, comprising the steps of:

[0035] (1) Add 100 grams of 80% ethanol and 10 grams of sodium ethylate in the reaction bottle to be mixed with an organic alkali-alcohol mixed solution;

[0036] (2) Add 22 grams of naringin into the prepared sodium ethoxide ethanol solution, heat up to 80°C, and react for 3 hours;

[0037] (3) Cool the reaction solution to 30°C, slowly add hydrochloric acid to adjust the pH to 6.5-7.0;

[0038] (4) the reaction solution obtained in step (3) is concentrated to the system without alcohol, and then diluted with 100 grams of water;

[0039] (5) Reduce the reaction system of step (4) to 25° C., filter, wash the filter cake with 50 grams of water, and vacuum-dry the filter cake at 70° C. for 14 hours to obtain 15.42 grams of off-white powdery solid, with a weight yield of 70% and a content of 98.4 %.

Embodiment 3

[0041] A preparation method of root bark acetophenone-4'-β-neohesperidoside, comprising the steps of:

[0042] (1) Add 200 grams of 80% ethanol and 10 grams of sodium ethylate in the reaction bottle to be mixed with an organic alkali-alcohol mixed solution;

[0043] (2) Add 42 grams of naringin into the prepared sodium ethoxide ethanol solution, heat up to 75°C, and react for 5 hours;

[0044] (3) Cool the reaction solution to 25°C, slowly add hydrochloric acid to adjust the pH to 6.5-7.0;

[0045] (4) the reaction solution obtained in step (3) is concentrated to the system without alcohol, and then diluted with 200 grams of water;

[0046] (5) Reduce the reaction system of step (4) to 30°C, filter, wash the filter cake with 100 grams of water, and vacuum-dry the filter cake at 80°C for 10 hours to obtain 27.7 grams of off-white powdery solid, with a weight yield of 66% and a content of 98%. .

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Abstract

Relating to the field of organic chemical synthesis, the invention discloses a synthesis process of phloroacetophenone-4'-beta-neohesperidoside. The process uses naringin as the raw material to prepare phloroacetophenone-4'-beta-neohesperidoside, and the process includes: adding naringin into an organic alkali alcoholic solution made of low-carbon alcohol and organic alkali, conducting heating reflux to 70-85DEG C, carrying out reaction for 2-5h, performing cooling, adding hydrochloric acid to adjust the PH to 6.5-7.0, conducting atmospheric concentration to no alcohol in the system, and washing the filter cake with water to obtain almost white powder solid phloroacetophenone-4'-beta-neohesperidoside. Compared with the existing synthesis process of phloroacetophenone-4'-beta-neohesperidoside, the synthesis process provided by the invention has the advantages of low cost, high yield, high purity, small environmental pollution, etc. The process provided by the invention can greatly reduce the damage to glycoside and flavones in naringin, and make the weight yield of phloroacetophenone-4'-beta-neohesperidoside reach 66%-70%.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a synthesis process of root bark acetophenone-4'-β-neohesperidoside. Background technique [0002] Neohesperidin is a dihydroflavonoid compound, which has activities such as scavenging free radicals, promoting gastric motility, lowering blood lipids, anti-atherosclerosis, protecting the nervous system, anti-allergic, and anti-cancer, and has a wide range of uses in medicine Neohesperidin is also an important intermediate, which can be converted into its derivative neohesperidin dihydrochalcone under certain conditions, and this compound is a safe low-calorie sweetener (sweetness of l500-1800 times of sucrose), widely used in food, beverage, pharmaceutical and animal feed industries. [0003] U.S. Patent Publication No. US3947405 discloses a synthesis process of neohesperidin dihydrochalcone. The synthesis process uses naringin as a raw material, water as a solvent, and ...

Claims

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Application Information

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IPC IPC(8): C07H15/203C07H17/07C07H1/00
CPCC07H1/00C07H15/203C07H17/07
Inventor 石磊饶洁王余兵
Owner XIANGXI HUALI PHARMA
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