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Ascorbic acid derivates, their preparation methods, intermediates and uses in cosmetics

A technology of ascorbic acid and derivatives, applied in cosmetics, cosmetics, sugar derivatives, etc., which can solve the problems of no superiority in physiological activity and no obvious improvement in stability, and achieve good stability

Active Publication Date: 2011-08-03
南京枫华投资管理有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] Ascorbic acid saccharide derivatives substituted at the 3-O-position have only been studied in a small amount, and the sugars in the derivatives are limited to monosaccharides; compared with other known ascorbic acid saccharide derivatives, their stability has not been significantly improved, and their physiological activity has no superiority
Other 3-O-sugar substituted ascorbic acid derivatives have not been reported

Method used

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  • Ascorbic acid derivates, their preparation methods, intermediates and uses in cosmetics
  • Ascorbic acid derivates, their preparation methods, intermediates and uses in cosmetics
  • Ascorbic acid derivates, their preparation methods, intermediates and uses in cosmetics

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Preparation of 1-Bromohepta-O-acetyllactose (3a)

[0067]Add 180mL of acetic anhydride to a three-necked flask equipped with a thermometer and a dropping funnel, cool in an ice-salt bath to 0°C, slowly add 0.6mL of perchloric acid dropwise, and control the internal temperature at 0-5°C, remove the ice after adding salt bath. At room temperature, 50.0 g of anhydrous lactose was added in batches, and the internal temperature was controlled at 33°C. After the addition, the reaction solution was cooled to 10°C, and 7.5g of red phosphorus was added. After stirring and dispersing, 14.5mL of bromine was added dropwise to the reaction solution. The internal temperature was lower than 20°C. Add 10.0mL of ice water to control the temperature of the reaction solution below 15°C. After dropping, stir at room temperature for 2.0h, pour into ice water, extract with chloroform several times, combine the organic phases, dry over anhydrous magnesium sulfate, and concentrate Dissolve t...

Embodiment 2

[0069] Preparation of 5,6-O-isopropylidene-L-ascorbic acid (7)

[0070] Add 91.0g of ascorbic acid and 450ml of acetone to a dry 1L three-necked flask, cool in an ice-salt bath to -5°C, slowly add 200.0g of concentrated sulfuric acid dropwise, keep the internal temperature at 0-5°C, drop it in about 2.5h, continue stirring for 5.0 min, remove the ice-water bath, naturally warm up to room temperature, continue to react for 45min, the reaction solution turns from colorless to light yellow, filter with suction, wash the filter cake several times with a small amount of acetone until the pH value is neutral, and vacuum-dry the filter cake (50°C ) for 1-2h, 89.5g of white powdery solid was obtained, its m.p.: 215-217°C, yield: 80.2%.

Embodiment 3

[0072] Preparation of 3-O-(hepta-O-acetyl-D-lactosyl)-(5,6-O-isopropylidene)-L-ascorbic acid (4a)

[0073] In a dry 1L round bottom flask, add 79.0g of 1-bromohepta-O-acetyllactose (3a), 28.1g of 5,6-O-isopropylidene-L-ascorbic acid (7), 500ml of acetone, and stir to disperse Then, add 28.0g potassium carbonate and 1.0g TEBAC, heat overnight at 50°C, filter with suction, recover the solvent to obtain a light yellow oil, which is then dissolved in 200mL ethyl acetate, washed several times with 20ml saturated saline, and anhydrous Dry over sodium sulfate, recover ethyl acetate, and vacuum-dry the residue with an oil pump for 1 h to obtain 57.0 g of light yellow foamy solid, melting point 52.5-54.0°C, yield: 60.2%.

[0074] 1 HNMR (CDCl 3 , 400M) δ: 1.21 (6H, -CH 3 ), 2.03-2.21 (21H, -CH 3 ), 3.98 (2H, -CH 2 -), 4.32 (2H, -CH 2 -), 4.37 (2H, -CH 2 -), 4.45(1H, -CH-), 4.47(1H, -CH-), 4.49(1H, -CH-), 4.50(1H, -CH-), 4.52(1H, -CH-), 4.54( 1H, -CH-), 4.61(1H, -CH-), 4.65(1H, ...

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Abstract

The invention relates to an ascorbic acid derivates 3-O-glyco-L-ascorbic acid, their preparation methods, intermediates and uses in cosmetics. The derivates used as vitamin C precursors have better physiological effect than 2-O-a-D-glucopyranosyl ascorbic acid (AA-2G) and are more stable. Present compounds can be used in many fields, such as in cosmetics, pharmaceuticals, foodstuffs and livestockfeed, and especially as whitening agents in cosmetics. The preparation method involves protecting the 5,6-dihydroxyl of ascorbic acid, then coupling with 1-haloacylglycosyl, obtaining the intermediate 3-O-(acylglycosyl)-(5,6-O-isopropylidine)-L-ascorbic acid, removing the isopropylidine and acyl from the intermediates, thereby obtaining the target substance.

Description

technical field [0001] The present invention relates to a derivative of ascorbic acid, its preparation method and related intermediate product and the application of the derivative in cosmetics; especially relates to 3-O-glycosyl-L-ascorbic acid, its preparation method and related Intermediate product, and the application of the derivative in cosmetics. Background technique [0002] L-ascorbic acid, namely vitamin C (referred to as VC), participates in many physiological activities in humans or animals. Due to the lack of enzymes to synthesize ascorbic acid, vitamin C cannot be synthesized by humans or animals and must be supplied by food. Therefore, it is listed as an essential nutrient element for humans or animals, and plays an irreplaceable role in the protection of human health and animal growth. important role. Clinically, ascorbic acid is mainly used to prevent and treat scurvy and resist infectious diseases, promote the healing of wounds and fractures, and is used ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/62A61Q1/00A61Q19/00A61K31/375
CPCA61K8/676C07D307/62C07H17/04A61Q19/02
Inventor 李华山史鲁秋
Owner 南京枫华投资管理有限公司
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