Preparation method and application of acetylated sodium hyaluronate

A technology of sodium hyaluronate and hyaluronic acid, applied in the field of preparation of acetylated sodium hyaluronate, can solve the problems of complicated process, large amount of organic solvent used and the like, achieve simple preparation process, reduce production process and shorten production cycle Effect

Active Publication Date: 2019-01-15
BLOOMAGE BIOTECHNOLOGY CORP LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems of large amount of organic solvent used and cumbersome process in the prior art, the present invention provides a method for preparing acetylated sodium hyaluronate that is more suitable for industrial production

Method used

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  • Preparation method and application of acetylated sodium hyaluronate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Take 5g of sodium hyaluronate powder with a molecular weight of 1300 kDa, add it to a 250ml three-necked flask, use 30ml acetic acid and 60ml acetic anhydride (V 乙酸 :V 乙酸酐 = 1:2) as an acylation reagent and reaction solvent, under mechanical stirring, use an ice-water bath to cool down until the internal temperature drops below 10°C, slowly add 2.2ml of concentrated sulfuric acid dropwise, after the dropwise addition, set the reaction temperature to 30°C, stop the reaction when the reaction solution is transparent. Slowly add the reaction solution into 1L of purified water (about 10 times the volume of the reaction solution) and stir to precipitate a fibrous precipitate (acetylated hyaluronic acid), then wash the precipitate with 1L, 0.5L and 0.5L of purified water for 3 times, After each wash, filter to dryness, add purified water to prepare about 3% solution and adjust pH to 5.8 with 2mol / L NaOH solution. After the acetylated hyaluronic acid solid is fully dissolved...

Embodiment 2

[0029] Weigh 3g of sodium hyaluronate powder with a molecular weight of 500 kDa, add it to a 250ml three-necked flask, use 30ml acetic acid and 120ml acetic anhydride (V 乙酸 :V 乙酸酐 = 1:4) as an acylation reagent and reaction solvent, under mechanical stirring, use an ice-water bath to cool down until the internal temperature drops below 10°C, slowly add 1.5ml of concentrated sulfuric acid dropwise, after the dropwise addition, set the reaction temperature to 5°C, stop the reaction when the reaction solution is transparent. Slowly add the reaction solution into 4L of purified water (about 20 times the volume of the reaction solution) and stir to precipitate a fibrous precipitate (acetylated hyaluronic acid), then wash the precipitate with 2L, 1L and 1L of purified water for 3 times, each time After washing, all were suction-filtered to dryness, and a 5% solution was prepared by adding purified water, and the pH was adjusted to 6.0 with 1mol / L NaOH solution. After the acetylate...

Embodiment 3

[0032] Weigh 10g of sodium hyaluronate powder with a molecular weight of 3000 kDa, add it to a 250ml three-necked flask, use 25ml acetic acid and 75ml acetic anhydride (V 乙酸 :V 乙酸酐 = 1:3) as an acylation reagent and reaction solvent, under mechanical stirring, use an ice-water bath to cool down until the internal temperature drops below 10°C, slowly add 5ml of concentrated sulfuric acid dropwise, after the dropwise addition, set the reaction temperature to 40 °C, stop the reaction when the reaction solution is nearly transparent. Slowly add the reaction solution into 0.2L of purified water (about 2 times the volume of the reaction solution) and stir to precipitate a fibrous precipitate (acetylated hyaluronic acid), then wash the precipitate with 1L, 1L and 1L of purified water for 3 times, each After washing for several times, they were suction filtered to dryness, and purified water was added to prepare about 8% solution, and the pH was adjusted to 6.8 with 1mol / L NaOH solut...

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Abstract

The invention provides a preparation method of acetylated sodium hyaluronate. The preparation method comprises following steps: adding hyaluronic acid or hyaluronate into a mixed solvent of acetic acid and acetic anhydride; carrying out acylation reactions under the catalytic action of concentrated sulfuric acid, after reactions, adding the reaction liquid into water to carrying out precipitation,filtering, washing the precipitate to obtain acetylated hyaluronic acid, adding alkali to adjust the pH value until the solution becomes neutral; filtering to remove the impurities, and carrying outspray drying to obtain acetylated sodium hyaluronate. The preparation time is largely shortened, precipitation and washing do not need a large amount of organic solvents, the environment is protected,the cost is reduced, and the preparation method is especially suitable for industrial large scale production.

Description

technical field [0001] The invention relates to a preparation method of acetylated sodium hyaluronate. Background technique [0002] Acetylated sodium hyaluronate is a derivative obtained by substituting acetyl groups on the four hydroxyl groups of the disaccharide structure of sodium hyaluronate (Hyaluronic acid, HA for short). The structure is as follows: [0003] . [0004] Commercial sodium acetylated hyaluronate is light yellow to white granules or powdery solid, soluble in water and 80% ethanol, and has more efficient moisturizing, repairing skin barrier and increasing skin elasticity than traditional sodium hyaluronate. There are few reports about sodium acetylated hyaluronate. The patent US005679657A published by Shiseido Co., Ltd. discloses a method for preparing sodium acetylated hyaluronate. After the acetylation reaction is completed, when washing acetylated hyaluronic acid A large amount of water was used, and during precipitation, a large amount of acetone ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
CPCC08B37/0072
Inventor 魏健李霞石艳丽王成山耿凤郭学平栾贻宏
Owner BLOOMAGE BIOTECHNOLOGY CORP LTD
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