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Method for preparing 3-O-alkyl ascorbic acid

A technology of alkyl ascorbic acid and alkylating reagent, which is applied in the field of preparation of 3-O-alkyl ascorbic acid, and can solve problems such as increased cost, large energy consumption, and cumbersome column chromatography

Inactive Publication Date: 2010-09-08
GUANGDONG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many problems in the silica gel column chromatography or ion exchange resin separation method reported in the above literature. The former has high production cost because silica gel cannot be reused, and the industrial column chromatography method is relatively cumbersome.
Although the latter resin can be reused and greatly reduces the amount of organic solvent used, it needs to concentrate a large amount of aqueous solution containing the product, which consumes a lot of energy and thus increases the cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] 17.6 grams (0.1 moles) of vitamin C, 50 milliliters of methanol, 11 grams (0.11 moles) of triethylamine, stirred and dissolved under nitrogen protection, added 20 grams (0.11 moles) of methyl p-toluenesulfonate, and reacted at room temperature for 4 hours, To the reaction solution was added 500 ml of ethyl acetate, followed by stirring for 15 hours. After filtration, the filtrate was concentrated to dryness, 300 ml of chloroform was added, and stirred at 5°C for 4 hours to obtain a white solid crude product. The crude product was recrystallized with ethyl acetate to obtain 8.2 g of 3-O-methylascorbic acid with a yield of 43% and a liquid phase content greater than 98%.

Embodiment 2

[0014] 352 mg (2 mmol) of vitamin C, 119 mg (2.2 mmol) of sodium methylate, 2 ml of ethanol, stirred under nitrogen protection, and 339 mg (2.2 mmol) of diethyl sulfate were added under reflux, and after 1 hour of reaction , down to room temperature, 20 ml of ethyl acetate was added to the reaction system, and stirred for 15 hours. After filtration, the filtrate was concentrated to dryness, 12 ml of chloroform was added, and stirred in an ice bath for 4 hours to obtain a white solid crude product. The crude product was recrystallized from ethyl acetate to obtain 167 mg of 3-O-ethyl ascorbic acid with a yield of 40% and a liquid phase content greater than 98%.

Embodiment 3

[0016] 352 milligrams (2 millimoles) vitamin C, 666 milligrams (2.8 millimoles) dipentyl sulfate, 283 milligrams (2.8 millimoles) triethylamine, 5 milliliters of ethanol were reacted under reflux for 3 hours, down to room temperature, to the reaction system 20 ml of ethyl acetate was added and stirred for 15 hours. After filtration, the filtrate was concentrated to dryness, 12 ml of chloroform was added, and stirred in an ice bath for 4 hours to obtain a white solid crude product. The crude product was recrystallized from ethyl acetate to obtain 247 mg of 3-O-pentyl ascorbic acid, the yield was 50%, and the liquid phase content was greater than 98%.

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Abstract

The invention discloses a method for preparing 3-O-alkyl ascorbic acid. The method comprises an etherification reaction step and a separation and purification step, wherein in the etherification reaction step, in a nitrogen atmosphere, vitamin C, alkali and an alkylating agent are mixed and dissolved in a solvent A to be reacted, and the reactants are reacted for 1 to 5 hours at room temperature and in a refluxing state to form solution of 3-O-alkyl ascorbic acid. The alkylating agent is one or more of toluene sulfonic acid, sulfuric ester and carbonate; the solvent A is one or more of methanol, ethanol, isopropyl alcohol, tetrahydrofuran and acetone; a molar ratio of the vitamin C to the alkali to the alkylating agent is 1:1-2:1-2; and a weight ratio of the solvent A to the vitamin C is 2-4:1. The preparation method has the advantages of simple method and low cost. The obtained 3-O-alkyl ascorbic acid is high in yield and purity.

Description

technical field [0001] The invention relates to a method for conveniently preparing 3-O-alkyl ascorbic acid from vitamin C, in particular to a process for preparing, separating and purifying high-purity 3-O-alkyl ascorbic acid crystals. Background technique [0002] Vitamin C, also known as L-ascorbic acid, has attracted much attention from the chemical, medical and nutritional circles since it was artificially synthesized in 1933. It has played an important role in cosmetics, food additives, medicine and health care and other industries. The allenol chemical structure of vitamin C makes it very easy to release hydrogen atoms and has excellent antioxidant properties. It can participate in various biological oxidation processes in the body, such as reducing dark oxidized melanin to light, and inhibiting Dopaquinone, an intermediate of melanin, is oxidized into melanin, which has the effect of whitening the skin. Vitamin C can promote the synthesis of collagen in cells, impr...

Claims

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Application Information

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IPC IPC(8): C07D307/62
Inventor 杨雪梅郑明彬
Owner GUANGDONG MEDICAL UNIV
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