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Method for synthesizing theanine

A synthesis method and theanine technology, applied in chemical instruments and methods, preparation of carboxylic acid amides, preparation of organic compounds, etc., can solve the problems of poor selectivity, slow reaction speed, low yield and the like

Inactive Publication Date: 2009-12-09
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These synthetic methods have shortcomings such as high production cost, slow reaction speed, poor selectivity, and low yield to varying degrees; using the above-mentioned methods, a small amount of D-type product will be produced in the synthetic process, which cannot be removed by chemical methods, which affects product quality.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0074] Weigh in a 1000ml three-necked bottle, add 60g of L-glutamic acid, 600ml of absolute ethanol, cool to 10°C under stirring, add 30ml of concentrated sulfuric acid dropwise, after the dropwise reaction at room temperature for 8 hours, add dropwise Triethylamine was neutralized, filtered after cooling, and the filter cake was dried to obtain 50 grams of L-glutamic acid-γ-ethyl ester with a yield of 70%.

[0075] In a 1000ml three-necked flask, add 40g of L-glutamic acid-γ-ethyl ester, add 600ml of ethanol aqueous solution, add 60g of sodium bicarbonate, dissolve and cool to 10°C, add 40ml of acetic anhydride dropwise, and dropwise Afterwards, react at room temperature for 3 hours, concentrate and desalinate to obtain L-N-acetyltheanine solution, add 300 ml of 70% ethylamine aqueous solution, stir the reaction until the ammoniation reaction is complete, and obtain L-N-acetyltheanine solution.

[0076] The L-N-acetyltheanine solution is concentrated, and the solution is chec...

example 2

[0078] Example 1 Weigh in a 1000ml three-necked bottle, add 60g of L-glutamic acid, 500ml of n-butanol, stir and cool to below 10°C, add 30ml of concentrated sulfuric acid dropwise, after the dropping, react at room temperature for 12 After 1 hour, triethylamine was added dropwise until neutral, filtered after cooling, and the filter cake was dried to obtain 66.6 g of L-glutamic acid-γ-n-butyl ester with a yield of 80%.

[0079] In a 1000 ml three-necked flask, add 40 g of L-glutamic acid-γ-n-butyl ester, add 400 ml of ethanol aqueous solution, add 50 g of sodium bicarbonate, dissolve and cool below 10°C, add dropwise 50 ml of acetic anhydride, After dropping, react at room temperature for 2 hours, concentrate and desalt to obtain L-N-acetylglutamic acid-γ-n-butyl ester solution, add 400 ml of 70% ethylamine aqueous solution, stir and react until the ammoniation reaction is complete, and obtain L-N-acetylglutamate acid solution.

[0080] The L-N-acetyltheanine solution is con...

example 3

[0082] In a 1000 ml three-necked flask, add 60 grams of L-glutamic acid and 600 ml of absolute ethanol, cool to 10°C under stirring, add 30 ml of concentrated sulfuric acid dropwise, and react at room temperature for 8 hours, add triethyl ether dropwise The amine was neutralized, filtered after cooling, and the filter cake was dried to obtain 50 g of L-glutamic acid-γ-ethyl ester with a yield of 70%.

[0083] In a 1000ml three-neck flask, add 40g of L-glutamic acid-γ-ethyl ester, add 200ml of water, add 40g of sodium bicarbonate, dissolve and cool to 10°C, add 15ml of benzoyl chloride dropwise, and dropwise Afterwards, react at room temperature for 2 hours, concentrate and desalinate to obtain L-N-benzoylglutamic acid-γethyl ester solution, add 400 ml of 70% ethylamine aqueous solution, stir the reaction until the ammoniation reaction is complete, and obtain L-N-benzoylglutamate acid solution.

[0084] The L-N-benzoyltheanine solution is concentrated, and the solution is chec...

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Abstract

The invention relates to a method for synthesizing theanine, which comprises the following steps: aminating L-N-acyl glutamic acid-gamma-ester in 70-percent ethylamine aqueous solution to obtain L-N-acyltheanine; hydrolyzing the L-N-acyltheanine by adopting L-aminoacylase to remove the acyl group of the L-N-acyltheanine; and performing separation in ethanol aqueous solution to obtain high-quality L-theanine. The method combines the advantages of industrialized acyl hydrolyzation by the L-aminoacylase, uses cheap acyl group as a protective group, and uses the L-aminoacylase to hydrolyze the acyl group after reaction with the ethylamine aqueous solution to obtain the L-theanine. The method has the characteristics of low raw material price, low production cost, high selectivity, high reaction speed and high yield. The used raw materials and reagents are suitable for industrial production, the operation process is simple, and the product quality can be ensured.

Description

technical field [0001] The present invention relates to the synthetic method of theanine. Background technique [0002] Theanine (L-Theanine) is a unique amino acid in tea, accounting for 50% of amino acids, and its structural formula is: CH 3 CH 2 NHCOCH 2 CH 2 CH(NH 2 )COOH. It is the most important taste substance in tea. Theanine is a safe, non-toxic, natural food additive with multiple physiological functions. In foreign countries, it has been widely used in food such as beverages, baked snacks, frozen snacks, etc., but the application of theanine in the food field in China is still blank. Japan approved L-theanine as a food additive in 1964, and the U.S. FDA recognized L-theanine as a generally recognized safe substance in 1985. Recent animal and human experiments have shown (Ling Guanting, L-theanine and its physiological functions, food and oils. 2003.5, 46-49): L-theanine is a safe, effective, and no side effects of stimulation enhancer , is an excellent su...

Claims

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Application Information

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IPC IPC(8): C07C237/06C07C231/14C07C231/02C12P13/04A23L1/305A23L33/175
CPCY02P20/55
Inventor 朱廷哲张金荣侯庆林
Owner TIANJIN PHARMA GROUP CORP
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