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Method for synthesis of alpha-arbutin

A synthesis method and technology of arbutin, applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of low yield, difficult to achieve production, and single, and achieve industrialized production and purification. The effect of easy and easy industrial production

Inactive Publication Date: 2013-06-19
NANJING HUASHI NEW MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] year 2006, Carbohydrate Research, 341; 11; 2006; 1945 – 1947 Reported Lewis acid-catalyzed coupling of tetrabenzoylglucose trichloroacetimidate and hydroquinone to form α-glycoside, the ratio of α / β can reach up to 5, but the yield is slightly lower (56-79%)
[0018] The above methods are all α / β mixtures, which need to obtain a single isomer by separation means such as column chromatography, which is difficult to achieve in production

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0041] Preparation of High Purity α-Type Intermediate Using Dichloromethane as Solvent

[0042] Under the protection of nitrogen, add 10g of pentaacetylglucose, 5.64g of hydroquinone, 10g of boron trifluoride ether and 50mL of dichloromethane into a 100mL reaction bottle, heat and reflux for 72h, the reaction solution is neutralized by sodium bicarbonate, saturated saline After washing three times, drying over anhydrous magnesium sulfate, and concentrating, 10.2 g of a light brown oil was obtained, and the content of α-isomer was 95.1%.

[0043]

Embodiment 2

[0045] Preparation of High Purity α-Type Intermediate Using Chloroform as Solvent

[0046] Under the protection of nitrogen, add 10g of pentaacetylglucose, 5.64g of hydroquinone, 10g of boron trifluoride ether and 50mL of chloroform into a 100mL reaction bottle, heat and reflux for 48h, the reaction solution is neutralized by sodium bicarbonate, and washed three times with saturated saline , dried over anhydrous magnesium sulfate, and concentrated to obtain 9.7 g of brown oil, wherein the content of α-isomer was 92.6%.

[0047]

Embodiment 3

[0049] Alternative reaction to Example 1

[0050] The mixture of the α / β-arbutin intermediate of 10g equimolar ratio, 50mL dichloromethane, 10g boron trifluoride ether drop into 100mL flask, operate with embodiment 1, reflux 48h, get brown oily matter 9.5g, Among them, the α-isomer content is 95.6%.

[0051]

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Abstract

The invention discloses a method for the synthesis of alpha-arbutin. The method comprises: heating a substrate, boron trifluoride etherate and a certain amount of a reaction medium to 30-80 DEG C to react for more than 48h, neutralizing, washing, drying, and concentrating to obtain an alpha-type arbutin intermediate with a relatively high purity, and thus obtaining the alpha-arbutin after hydrolysis and recrystallization. The method of the invention can improve the proportion of alpha / beta-glucoside, or convert a beta-type arbutin intermediate into an alpha- type arbutin intermediate, alpha-type isomer in the obtained intermediate product is high in purity (>=92%), easy to purify, and the obtained alpha-arbutin product has a purity of more than 98%.

Description

technical field [0001] The invention relates to a method for synthesizing natural glycosides, in particular to a method for synthesizing α-arbutin. Background technique [0002] Arbutin (Arbutin, formula Ⅰ), that is, p-hydroxyphenyl-β-D-glucopyranoside, is a natural active substance derived from green plants. It can be used as a diuretic, an anti-infective drug for the urinary system, a stabilizer for color photography, and also has an antitussive effect. Since the 1980s, studies have found that arbutin, as a competitive inhibitor of tyrosinase, can inhibit the activity of the key enzyme tyrosinase in the process of melanin formation, so it has a whitening effect and is not irritating to the skin. The toxic and side effects are small. [0003] Japan's Shiseido Company first applied arbutin in whitening cosmetics. Arbutin is a skin depigmentation component that integrates "green plants, safe and reliable" and "high-efficiency depigmentation". Inhibit the activity of tyros...

Claims

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Application Information

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IPC IPC(8): C07H15/203C07H1/00
Inventor 史鲁秋苏桂珍薛虹宇
Owner NANJING HUASHI NEW MATERIAL
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