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Hydroxyalkanoic acid and hydroxyalkanoic acid oligomer esters of retinol

A retinyl ester, hydroxyl technology, applied in the field of retinyl ester and its preparation, can solve the problems of increasing cost, time and waste, unstable retinol or retinyl ester degradation, etc.

Inactive Publication Date: 2013-10-30
EASTMAN CHEM CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These processes use harsh reagents or high temperatures, reaction conditions that lead to degradation of unstable retinol or retinyl esters
Also, these methods are not suitable for those moieties with reactive groups, such as alcohols, unless the alcohol is protected
Protection and deprotection of hydroxyl groups add cost, time and waste to the synthesis of such molecules

Method used

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  • Hydroxyalkanoic acid and hydroxyalkanoic acid oligomer esters of retinol
  • Hydroxyalkanoic acid and hydroxyalkanoic acid oligomer esters of retinol
  • Hydroxyalkanoic acid and hydroxyalkanoic acid oligomer esters of retinol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Preparation of oligomers of retinyl-3-hydroxybutyrate (1a) (n=0-4)

[0064] In heptane, add retinol (58% retinol 25.9g, 15.0g retinol; 52.4mmol), ethyl 3-hydroxybutyrate (20.76g; 157mmol; 3 times equivalent) to the vial successively, and Novozym 435 (1.5g). The mixture was purged and stirred for 48 h at room temperature to obtain a mixture of oligomers of retinyl-3-hydroxybutyrate with a retinol conversion rate of 96.7%. The mixture was diluted with toluene (30ml), filtered to give a solid which was washed with toluene (30ml). The toluene solution was washed with water:methanol at a ratio of 1:1 (60ml), poured out the aqueous phase and extracted back with heptane (25ml), combined the organic layers, washed with water:methanol at a ratio of 1:1 (60ml), and washed with anhydrous sodium sulfate Dry and concentrate to give dark yellow oil 17.79g1a (R=CH 2 , R 1 =CH 3 ). HPLC (high performance liquid chromatography) analysis yielded 3.7% retinol and 95.5% 1a oligomers...

Embodiment 2

[0067] Preparation of retinyl ricinoleate (1b)

[0068] In toluene, add retinol (54% retinol 1.852g, 1.0g; retinol, 3.49mmol), ricinoleic acid (80% content; 1.250g; 4.19mmol; 1.2 times the equivalent ), and Novozym435 (1g). The mixture was sealed and stirred at room temperature for 21 h, and the conversion rate of retinol was 83% to obtain 1b.

[0069] HPLC (4.6x150mm Zorbax SB-C8 chromatographic column [Agilent], 3.5μ thickness, 90:10 methanol: water (containing 0.1% trifluoroacetic acid) detection time 7min, the gradient is converted into 95:5 methanol: water (containing 0.1% trifluoroacetic acid) within 1min 0.1% trifluoroacetic acid), maintain the concentration detection time for 12min, change the gradient to 100% methanol within 1min, maintain 100% methanol, and detect the wavelength at 325nm):t R 3.9min (retinol); t R 14.2min (1b).

Embodiment 3

[0071] Enzymatic hydrolysis of oligomers of retinyl-3-hydroxybutyrate (1a) (n=0-4)

[0072] The oligomer of retinyl-3-hydroxybutyrate (1a; 100 mg) was dissolved in 2 ml of toluene, a buffer solution (2 ml) with a pH value of 7 was added, Novozym 435 (100 mg) was added, and the mixture was vigorously stirred at room temperature , At 1, 24, and 48h, the supernatant was extracted and analyzed by HPLC. The results are shown in Table 1, and showed a large amount of hydrolysis at 48h. A control test without enzyme showed no hydrolysis after 48 hours.

[0073] Table 1 Enzymatic hydrolysis of oligomers of retinyl-3-hydroxybutyrate

[0074] time (h)

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Abstract

Retinyl hydroxyesters and retinyl oligo-hydroxyesters were prepared using a chemoenzymatic process from retinol and short chain esters of hydroxycarboxylic acids or short chain esters of hydroxycarboxylic acids. The presence of the hydroxyl group on the acid can result in a mixture of esters from various oligomers of the hydroxycarboxylic acid. The retinyl ester products are readily enzymatically hydrolyzed in vitro, which indicates that application to the skin should result in release of the anti-aging ingredient retinol (without the inherent instability and irritation) along with the acid, which, if chosen appropriately, should also have desirable biological effects. This combination should be effective as an anti-aging skin care ingredient.

Description

technical field [0001] The present invention relates to retinyl ester and its preparation method Background technique [0002] Retinol (vitamin A) and its derivatives have a long history of use in cosmetics as active ingredients that improve the overall appearance of the skin. Retinol itself is unstable and can be irritating when used in excess. Long-chain retinol esters are sometimes preferred because they are more stable and less irritating to the skin. It is hoped that these esters will be easily broken down on the skin into retinol for metabolism and efficacy. Because of the fatty acid content of retinol esters, the hydrolyzed fraction of fatty acids can provide additional benefits. In addition to fatty acids, other substances with various biological properties are also expected to be used in retinyl conjugates to enhance or extend biological gain. [0003] One of the chemical means for preparing retinyl ester is to react retinol with long-chain acid or chloride acyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/12C12P7/62A61K8/67A61Q19/00
CPCA61Q19/00C12P23/00C07C403/12C12P7/62C07C2101/16A61K8/85C07C2601/16A61K8/67
Inventor 尼尔·沃伦·波阿斯
Owner EASTMAN CHEM CO
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