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Method for synthesizing sclareolide under catalysis of immobilized epoxidase

The technology of sclareolide and cyclooxygenase is applied in the field of catalyzing and synthesizing sclareolide by immobilized epoxidase, can solve the problem of high product yield, and achieves lower reaction temperature, higher economic benefits and steps simple effect

Inactive Publication Date: 2016-06-22
SHANDONG RUIYING PIONEER PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The important intermediate in this synthesis reaction is epoxidized sclareol, but the epoxidation of sclareol with hydrogen peroxide is still very difficult, the reaction time is not less than 9 hours, and the product yield is the highest 72.4 %

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] First, add 6.16g of sclareol, 0.01g of immobilized cyclooxygenase, 20ml of dichloroethane and 5g of 30% hydrogen peroxide solution into the beaker, and adjust the pH value with 50% sulfuric acid 2, then transferred to a three-necked flask, magnetically stirred, and heated to 50°C. After reacting for 2 hours, separate the organic phase and the water phase, extract twice with dichloroethane, and combine with the organic phase. After recovering dichloroethane, add toluene and heat under reflux for 3 hours, dehydrate and recover toluene. The remaining product was distilled under reduced pressure to obtain 4.45 g of sclareolide, with a yield of 72.2%.

Embodiment 2

[0021] First, add 6.16g of sclareol, 0.01g of immobilized cyclooxygenase, 20ml of dichloroethane and 5g of 30% hydrogen peroxide solution into the beaker, and adjust the pH value with 50% sulfuric acid 2, then transferred to a three-necked flask, magnetically stirred, and heated to 50°C. After reacting for 3 hours, separate the organic phase and the water phase, extract twice with dichloroethane, and combine with the organic phase. After recovering dichloroethane, add toluene and heat under reflux for 3 hours, dehydrate and recover toluene. The remaining product was distilled under reduced pressure to obtain 5.12 g of sclareolide, with a yield of 83.1%.

Embodiment 3

[0023] First, add 6.16g of sclareol, 0.01g of immobilized cyclooxygenase, 20ml of dichloroethane and 5g of 30% hydrogen peroxide solution into the beaker, and adjust the pH value with 50% sulfuric acid 2, then transferred to a three-necked flask, magnetically stirred, and heated to 50°C. After reacting for 4 hours, separate the organic phase and the water phase, extract twice with dichloroethane, and combine with the organic phase. After recovering dichloroethane, add toluene and heat to reflux for 3 hours, dehydrate and recover toluene. The remaining product was distilled under reduced pressure to obtain 5.14 g of sclareolide, with a yield of 83.4%.

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Abstract

The invention belongs to the technical field of biochemical engineering and particularly discloses a method for synthesizing sclareolide under catalysis of immobilized epoxidase. According to the method, sclareol is taken as a starting material. The method is characterized in that sclareol, immobilized epoxidase, a hydrogen peroxide solution and dichloroethane are added to a beaker and react under the conditions that the pH value is 2 and the temperature is 50 DEG C, epoxidized sclareol is obtained, oxidative degradation is continuously performed under the action of hydrogen peroxide, hydroxy acid is obtained, methylbenzene is added, the mixture is heated for reflux, and sclareolide is obtained. The method has the advantages that the production technological conditions are mild, the steps are simple, the method is environment-friendly, the economic benefits are high and the like, the reaction time is greatly shortened, the reaction temperature is reduced, and the production cost is saved.

Description

(1) Technical field [0001] The invention belongs to the technical field of biochemical industry, in particular to a method for catalyzing the synthesis of sclareolactone by immobilized cyclooxygenase. (2) Background technology [0002] Sclareolactone is an extremely important intermediate for the synthesis of Ambrox, and it has been widely used in tobacco, alcohol, food additives, etc. as an aroma component of ambergris. At present, sclareolide is also used to synthesize some important pharmacologically active compounds such as anti-inflammatory and anti-cancer. Therefore, the synthesis of sclareolactone is also a hotspot in the research of the perfume industry. [0003] Although the method of preparing sclareolide by oxidative degradation of sclareol reported at home and abroad has made some progress, it has initially realized industrialization. However, the oxidative degradation of sclareyl ester is relatively complicated, and various methods have certain shortcomings. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92C12P17/02
CPCC07D307/92C12P17/02
Inventor 彭继先
Owner SHANDONG RUIYING PIONEER PHARMA
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