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Preparation method of amino acid phytosterol ester hydrochloride

A technology of phytosterol ester hydrochloride and phytosterol ester, which is applied in the field of preparing phytosterol derivatives, can solve the problems that amino acid phytosterol ester cannot be obtained, glutamic acid phytosterol ester cannot be obtained, etc. The effect of stable nature and wide application range

Inactive Publication Date: 2014-04-16
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is only one document about the report of amino acid phytosterol esters. People such as Pang use sodium bisulfate monohydrate as a catalyst and n-butanol as a solvent. Phytosterols and glutamic acid react at 70-90°C for 6-10 hours. But repeating this test, can not get phytosterol glutamate, try other amino acids, make it react with phytosterol under the same reaction conditions, can not get the corresponding amino acid phytosterol ester

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 0.6894g (3.6mmol) EDC and 0.606g (5.4mmol) Et in the reaction flask 3 N, add anhydrous dichloromethane to dissolve, then add 0.4392g (3.6mmol) DMAP and 0.525g (3mmol) N-BOC-glycine, stir magnetically under ice bath at 0°C for 1 hour, then add 0.824g (2mmol) soybean For sterols, stir and react in an ice bath at 0°C for 8 hours, then rise to 25°C and react at room temperature for 16 hours, use TLC to monitor the reaction process, and HPLC to measure the esterification rate. After the reaction, the crude product of N-BOC-glycine stigmasterol ester is obtained , separated and purified by silica gel column chromatography to obtain a pure product with a yield of 96.6%.

[0025] Dissolve 0.569 g (1 mmol) of pure N-BOC-glycine stigmasteryl ester in 50 mL of 3 mol / L hydrogen chloride / ethyl acetate solution, and react with magnetic stirring at room temperature for 0.5 hours, then remove the hydrogen chloride / ethyl acetate solvent by rotary evaporation under reduced pressure ...

Embodiment 2

[0030] Add 0.6894g (3.6mmol) EDC and 0.606g (5.4mmol) Et in the reaction flask 3 N, add anhydrous dichloromethane to dissolve, then add 0.4392g (3.6mmol) DMAP and 0.741g (3mmol) N-BOC-glutamic acid, stir magnetically in an ice bath at 0°C for 1 hour, then add 0.824g (2mmol) ) stigmasterol, stirred and reacted in an ice bath at 0°C for 8 hours, then rose to 25°C and reacted for 16 hours at room temperature, adopted TLC to monitor the reaction process, HPLC to measure the esterification rate, and obtained N-BOC-glutamic acid beans after the reaction The crude sterol ester was separated and purified by silica gel column chromatography to obtain a pure product with a yield of 95.8%.

[0031] Dissolve 0.641 g (1 mmol) of pure N-BOC-stigmasteryl glutamate in 50 mL of 3 mol / L hydrogen chloride / ethyl acetate solution, and react with magnetic stirring at room temperature for 0.5 hours, and remove the hydrogen chloride / ethyl acetate by rotary evaporation under reduced pressure. ester s...

Embodiment 3

[0036] Add 0.6894g (3.6mmol) EDC and 0.606g (5.4mmol) Et in the reaction flask 3 N, add anhydrous dichloromethane to dissolve, then add 0.4392g (3.6mmol) DMAP and 0.699g (3mmol) N-BOC-aspartic acid, stir magnetically for 1 hour in an ice bath at 0°C, then add 0.824g ( 2mmol) stigmasterol, stirred and reacted in an ice bath at 0°C for 8 hours, then rose to 25°C and reacted for 16 hours at room temperature, using TLC to monitor the reaction process, HPLC to measure the esterification rate, and N-BOC-aspartic acid was obtained after the reaction was completed The crude sour stigmasteryl ester was separated and purified by silica gel column chromatography to obtain a pure product with a yield of 95.2%.

[0037] Dissolve 0.627 g (1 mmol) of pure N-BOC-aspartic acid stigmasteryl ester in 50 mL of 3 mol / L hydrogen chloride / ethyl acetate solution, magnetically stir the reaction at room temperature for 0.5 hours, and remove hydrogen chloride / acetic acid by rotary evaporation under redu...

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Abstract

The invention relates to a preparation method of amino acid phytosterol ester hydrochloride. The invention adopts the following technical scheme: catalyzing esterification of phytosterol and N-t-butyloxycarboryl amino acid by using 1-(3-dimethylamino propyl)-3-ethyl carbodiimide hydrochloride, 4-dimethylamino-pyridine and a triethylamine composite catalyst; reacting below 0 DEG C for 2-10 hours; heating to the room temperature and continuously reacting at 25 DEG C for 1-22 hours to obtain a reaction mixture; separating and purifying the reaction mixture by adopting slica column chromatography to obtain N-t-butyloxycarboryl amino acid phytosterol; dissolving the N-t-butyloxycarboryl amino acid phytosterol into 3-4mol / L of hydrogen chloride / ethyl acetate solution; stirring and reacting at the room temperature of 25 DEG C for 0-2 hours; carrying out vacuum rotary evaporation to remove a hydrogen chloride / ethyl acetate solvent, so as to obtain the amino acid phytosterol ester hydrochloride. The method is simple to implement, and low in energy consumption, and the amino acid phytosterol ester hydrochloride is high in yield, stable in product property and easy to store.

Description

technical field [0001] The invention relates to a method for preparing phytosterol derivatives, in particular to a method for preparing amino acid phytosterol ester hydrochloride. The application and development of this product involves technical fields such as food, medicine, chemical industry and cosmetics. Background technique [0002] Phytosterols are a class of steroidal compounds with cyclopentaneperhydrophenanthrene as the main skeleton, which have a very good cholesterol-lowering effect. In recent years, it has also been found that phytosterols play an important role in anti-cancer, anti-inflammation, anti-virus, and improving immunity. They can be used as emulsifiers in the cosmetics industry and have received more and more attention. [0003] However, free phytosterols are crystalline and insoluble, neither soluble in water nor soluble in oil, which limits its application in food. At present, phytosterols are generally only added to fat foods, and their applicati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00C07J75/00
Inventor 贾承胜刘萍林蔚婷张晓鸣
Owner JIANGNAN UNIV
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