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Preparation method of L-carnosine

A carnosine and histidine technology, applied in organic chemistry and other directions, can solve problems such as impact on application, pollution, low total yield, etc., and achieve the effects of being beneficial to industrial production, simple process, and low environmental pollution

Inactive Publication Date: 2010-03-17
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These synthetic methods all have the following problems, for example: product racemization, difficult selection of solvent, difficulty in separation, etc.
Generally speaking, the current synthesis method of L-carnosine basically has the disadvantages of many reaction steps, low overall yield, serious pollution and high cost.
[0007] Although the patent US 4359416A discloses: in the presence of tetraalkyl ammonium hydroxide or tetraaryl ammonium hydroxide, tetrahydro-1,3-thiazine-2,6-dione and L-histidine react to prepare L- A new method for carnosine, but tetraalkyl ammonium hydroxide or tetraaryl ammonium hydroxide is very expensive and used in a large amount, resulting in high product cost, which affects the practical application of the method

Method used

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  • Preparation method of L-carnosine
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  • Preparation method of L-carnosine

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Dissolve 21.7g of L-histidine (II) in 210ml of water, adjust the pH to 9.0 with trimethylamine; add 24.6g of tetrahydro-1,3-thiazine-2,6-bis in batches within 40 minutes at 10°C Ketone (III), and use trimethylamine to control the pH to 8.5, continue to stir and react for 30 minutes after the addition is complete; use formic acid to adjust the pH of the reaction solution to 4.2, stir until no bubbles are formed, and then use trimethylamine to adjust the pH to 8.2; dehydration under reduced pressure until transparent Viscous liquid, cooled to room temperature; add 1200ml of absolute ethanol, stir until white precipitate appears, filter with suction, successively soak with 95% ethanol, dichloromethane, ether, filter, dry to obtain 27.9g of white powdery solid, collected The yield is 88.1%, and the melting point is 243-247°C.

Embodiment 2

[0024] Dissolve 21.7g of II in 210ml of water, adjust the pH to 9.0 with trimethylamine; add 24.6g of III in batches within 40 minutes at 25°C, and control the pH to 8.5 with trimethylamine, and continue to stir for 30 minutes after the addition; adjust the pH with formic acid 4.2, Stir until no bubbles are formed, then adjust the pH to 8.2 with trimethylamine; dehydrate under reduced pressure until it becomes a transparent viscous liquid, cool to room temperature; add 1200ml of absolute ethanol, stir until white precipitate appears, filter with 95% Soak in ethanol, dichloromethane and ether, filter, and dry to obtain 23.6 g of white powdery solid, yield 74.5%, melting point: 240-245°C.

Embodiment 3

[0026] Dissolve 21.7g of II in 210ml of water, adjust the pH to 9.0 with trimethylamine; add 24.6g of III in batches within 40 minutes at 0°C, and control the pH to 8.5 with trimethylamine, and continue stirring for 30 minutes after the addition; adjust the pH with formic acid 4.2, Stir until no bubbles are formed, then adjust the pH to 8.2 with trimethylamine; dehydrate under reduced pressure until it becomes a transparent viscous liquid, cool to room temperature; add 1200ml of absolute ethanol, stir until white precipitate appears, filter with 95% Soak in ethanol, dichloromethane, and ether, filter, and dry to obtain 20.1 g of white powdery solid, yield 63.5%, melting point: 240-244°C.

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Abstract

The invention relates to an improved preparation method of L-carnosine. The preparation method comprises the following steps: taking water as reaction solvent at the reaction temperature from 0 to 30DEG C, adjusting the pH value of the reaction solution of L-histidine showed in a formula (II) and tetrahydro-1, 3-thiazine-2, 6-diketone showed as a formula (III) to be 8.2-9.2 by trimethylamine andcarrying out the reaction, and carrying out the separating treatment to the reaction solution after the reaction is finished to obtain the L-carnosine shown in a formula (I), wherein the mass ratio between the L-histidine and the tetrahydro-1, 3-thiazine-2,6-diketone is 1: 1.01 to 1.27. The invention provides a novel L-carnosine synthesis process which has simple process, easily-obtained raw materials, low production cost and less environment pollution, and is beneficial to industrial production.

Description

(1) Technical field [0001] The invention relates to a preparation method of L-carnosine. (2) Background technology [0002] L-carnosine (CAS: 305-84-0, Carnosine) was discovered in innervated tissues of vertebrates as early as 1900. L-carnosine is mainly found in the skeletal muscles of vertebrates, such as pork, beef, chicken, etc., especially in chicken breast meat; for humans, it is in the most active department of aerobic metabolism-muscle and brain exist in higher concentrations in tissues. [0003] L-carnosine is an endogenous dipeptide composed of β-alanine and L-histidine, and its structural formula is shown in I: [0004] [0005] As an important dipeptide, L-carnosine can participate in and regulate various physiological activities of the human body. It has excellent natural anti-oxidation, anti-free radical, anti-aging, neuroprotective, vascular relaxation, and fatigue-relieving functions. It has been used in medicine , health care, food, cosmetics and other...

Claims

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Application Information

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IPC IPC(8): C07D233/64
Inventor 钟光祥朱平楼良弟田青蒋剑松胡惟孝
Owner ZHEJIANG UNIV OF TECH
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