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Method for synthesizing hydroxypinacolone retinoate (HPR) under catalysis of biological enzyme

A synthetic method, the technology of retinoic acid ester, applied in the field of synthesis of hydroxypinacolone retinoic acid ester, can solve the problems such as not very effective industrial operation, and achieve good substrate stability, high enzyme conversion rate, and high purity Effect

Pending Publication Date: 2021-03-19
SHANGHAI COACHCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] For the synthesis of HPR, there is no very effective and easy-to-industrial method in the published literature.

Method used

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  • Method for synthesizing hydroxypinacolone retinoate (HPR) under catalysis of biological enzyme

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] In a 500mL three-necked flask, add 200mL of 0.1M pH 8.0 PBS buffer solution, 0.2g of acyltransferase MsAcT, 10g of methyl retinoate, 1-hydroxy-3,3-dimethylbutan-2-one 4 g was reacted for 24 h at 25° C., stirred by a 200 rpm stirring paddle, and purged with 0.01 MPa nitrogen, and the conversion rate was 95% as determined by HPLC. Add hydrochloric acid to adjust the pH to 2-3, filter with celite, add an equal volume of ethyl acetate to extract twice, and rotary evaporate to obtain 10.2 g of the product with a purity of 98%.

Embodiment 2

[0018] In a 500mL three-neck flask, add 200mL of 0.1M pH 8.5 PBS buffer solution, 0.2g of acyltransferase MsAcT, 10g of methyl retinoate, 1-hydroxy-3,3-dimethylbutan-2-one 5 g was reacted for 24 h at 30° C., stirred by a stirring paddle at 200 rpm, and purged with nitrogen gas at 0.01 MPa, and the conversion rate was 95% as determined by HPLC. Add hydrochloric acid to adjust the pH to 2-3, filter with diatomaceous earth, add an equal volume of ethyl acetate to extract twice, and rotary evaporate to obtain 11.2 g of the product with a purity of 98%.

Embodiment 3

[0020] In a 500mL three-neck flask, add 200mL of 0.1M pH 9 PBS buffer solution, 0.2g of acyltransferase MsAcT, 10g of methyl retinoate, 1-hydroxy-3,3-dimethylbutan-2-one 6 g, at 30° C., stirring with a 200 rpm stirring paddle, and purging with 0.01 MPa nitrogen, reacted for 24 hours, and the conversion rate was 95% as detected by HPLC. Add hydrochloric acid to adjust the pH to 2-3, filter with diatomaceous earth, add an equal volume of ethyl acetate to extract twice, and rotary evaporate to obtain 11.1 g of the product with a purity of 98%.

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Abstract

The invention belongs to the field of biological organic synthesis, medical health care and daily chemicals, and particularly relates to a method for synthesizing hydroxypinacolone retinoate (HPR) under catalysis of a biological enzyme. According to the method, retinoate and 1-hydroxy-3,3-dimethylbutane-2-keone are used as raw materials, and react in an aqueous phase buffer solution containing acyltransferase and having the pH value of 7.0-10.0 so as to prepare the HPR. The method is easy and convenient to operate, reagents are cheap and easy to obtain, in the whole preparation process, the substrate stability is good, the enzyme conversion rate is high, the product purity is high, and the method has good industrial application prospects.

Description

technical field [0001] The invention belongs to the fields of bioorganic synthesis, medicine and health care, and daily chemicals, and in particular relates to a method for synthesizing hydroxy pinacolone retinoate catalyzed by biological enzymes. Background technique [0002] Hydroxypinacolone retinoate, CAS number is 893412-73-2, referred to as HPR, it belongs to the retinoids (Retinoids) family, has the function of regulating the metabolism of the epidermis and stratum corneum, can resist aging, and can reduce seborrhea , dilute epidermal pigment, prevent skin aging, prevent acne, whiten and lighten spots, etc. Simple retinol is less stable and more irritating. These problems can be solved by side chain modification, such as retinyl palmitate, which is much milder. But the problem with the modification of the side chain is that the conversion steps are increased, and the potency will be affected. Hydroxypinacolone retinoate (HPR) is a retinol derivative modified by hydr...

Claims

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Application Information

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IPC IPC(8): C12P7/64
CPCC12P7/6436
Inventor 吴江张伟朱纯银周宝萍
Owner SHANGHAI COACHCHEM TECH
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