Method for synthesizing ascorbyl glucoside

A technology of ascorbic acid and glucoside, which is applied in the field of synthesizing L-ascorbic acid-2-glucoside, can solve problems such as difficult crystallization and separation of by-products, and achieve increased crystallization yield, reduced separation and purification difficulty, improved purity and Yield effect

Inactive Publication Date: 2020-01-31
安徽泰格生物技术股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The molecular weight of these two by-products is the same as that of the target product L-ascorbic acid-2-glucoside, so it is difficult to separate the by-products during purification, making it difficult to crystallize the target product L-ascorbic acid-2-glucoside from a supersaturated solution

Method used

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  • Method for synthesizing ascorbyl glucoside
  • Method for synthesizing ascorbyl glucoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a 250ml dry three-neck round bottom flask with stirring and thermometer, add 25g of L-ascorbic acid and 150ml of acetone, put the reaction system in a 30°C water bath, start stirring, and add 2ml of acetyl chloride under strong stirring, After reacting for 2 hours, add 2ml of acetyl chloride again, continue the reaction for 2 hours, filter with suction, and dry under reduced pressure to obtain a white needle-like solid, which is the product of 5,6-O-isopropylidene-L-ascorbic acid, with a molecular weight of 216.19, The measured melting point was 217°C (dec.).

[0027] Take 5g of β-cyclodextrin, put it in 65ml of 5,6-O-isopropylidene-L-ascorbic acid aqueous solution with a concentration of 86g / L, then add 0.70g of cysteine, and then put it at 37°C Incubate in a water bath for 10 minutes, then adjust the pH of the feed solution to 5-6, add 10ml (600U / ml) of cyclodextrin glucosidyl transferase, place the reaction system in a shaker, and keep it warm for 37 minutes under...

Embodiment 2

[0031] In this example, the crystallized feed liquid obtained in Example 1 was used, and 4 g of β-cyclodextrin and 4.34 g of 5,6-O-isopropylidene- L-ascorbic acid, then add 0.70g of cysteine, then keep it in a water bath at 37°C for 10min, then adjust the pH of the feed solution to 5-6, add 8ml (600U / ml) of cyclodextrin glucoside transferase , put the reaction system in a shaker, keep it warm at 37°C for 24 hours under the condition of avoiding light and oxygen, and keep the pH at about 5.5; then raise the temperature of the feed solution to 42°C, add 1ml of α-1,4-glucose for hydrolysis Enzyme (100,000 U / ml), continue to react for 3 hours, and the reaction is completed; the feed liquid obtained from the reaction is separated through a strong acid cation exchange resin, and the strong acid cation exchange resin is a sulfonic acid based on a styrene-divinyl copolymer. Based on cation exchange resin, 5.61g of L-ascorbic acid-2-glucoside in the obtained separation liquid was purif...

Embodiment 3

[0033] In this example, the crystallized feed liquid obtained in Example 2 was used, and 3 g of β-cyclodextrin and 3.35 g of 5,6-O-isopropylidene- L-ascorbic acid, then add 0.70g of cysteine, and then keep it in a water bath at 37°C for 10 minutes, then adjust the pH of the feed solution to 5-6, and add 6ml (600U / ml) of cyclodextrin glucoside transferase , put the reaction system in a shaker, keep it warm at 37°C for 24 hours under the condition of avoiding light and oxygen, and keep the pH at about 5.5; then raise the temperature of the feed solution to 42°C, add 1ml of α-1,4-glucose for hydrolysis Enzyme (100,000 U / ml), continue to react for 3 hours, and the reaction is completed; the feed liquid obtained from the reaction is separated through a strong acid cation exchange resin, and the strong acid cation exchange resin is a sulfonic acid based on a styrene-divinyl copolymer. Based on cation exchange resin, 5.50g of L-ascorbic acid-2-glucoside in the obtained separation liq...

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Abstract

The invention belongs to the technical field of biochemical synthesis, and particularly discloses a method for synthesizing ascorbyl glucoside. The method includes: using 5,6-O-isopropylidene-L-ascorbic acid as a starting material, and firstly reacting to obtain 5,6-O-isopropylidyl-ascorbyl glucoside, separating the reaction solution with a strongly acidic cation exchange resin, hydrolyzing the 5,6-O-isopropylidyl-ascorbyl glucoside to obtain ascorbyl glucoside, and then crystallizing and drying to obtain the ascorbyl glucoside product, and the remaining material liquid after crystallization can be recycled to use. The method can effectively avoid generation of byproducts, reduce difficulty of subsequent separation and purification, and improve purity and yield of the ascorbyl glucoside product.

Description

technical field [0001] The invention relates to the technical field of biochemical synthesis, in particular to a method for synthesizing L-ascorbic acid-2-glucoside. Background technique [0002] The structural formula of L-ascorbic acid-2-glucoside (that is, 2-O-α-D-glucopyranosyl-L-ascorbic acid) is shown in formula (I), and L-ascorbic acid-2-glucoside is used as L-ascorbic acid The important derivative is one of the whitening additives announced and approved by the Department of Health, and is recognized as the most stable L-ascorbic acid derivative. L-Ascorbic acid-2-glucoside is currently the most commonly used whitening ingredient in cosmetic products of major brands. L-Ascorbic acid-2-glucoside not only has a good whitening effect, but also has stable chemical properties and no irritation to the skin, so it is widely used in the production of cosmetics at home and abroad. L-ascorbic acid-2-glucoside entering human cells is hydrolyzed by α-glucosidase to generate asc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/60C12P19/18C12P19/14
CPCC12P19/14C12P19/18C12P19/60
Inventor 王珂周友超陈修陈斌朱东来
Owner 安徽泰格生物技术股份有限公司
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