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Preparation method of L-carnosine

A technology of carnosine and products, applied in the field of organic compound preparation, to achieve the effects of quality assurance, elimination of possibility, and elimination of hydrazine residues

Active Publication Date: 2013-07-10
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far, there is no corresponding technical suggestion in the published Chinese and foreign patents and non-patent literature to prepare hydrazine-free carnosine. For this reason, the applicant has found a solution to the problem after many explorations. On the basis of technology, by using other non-hydrazine deprotection reagents to remove phthaloyl group, remove the source of hydrazine from the source, and prove this method by detecting the finished L-carnosine product obtained by using this technology It is completely effective and completely solves the problem of hydrazine residue in the product of L-carnosine prepared by the current mainstream hydrazinolysis method. The technical solution to be introduced below is produced under this background

Method used

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

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Experimental program
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Effect test

Embodiment 1

[0023] Add 7.12 grams (2 mmol) of phthaloyl-L-carnosine and 80 mL of monomethylamine aqueous solution (30%, mass ratio) to a 250 mL reaction flask, and stir the mixed system at 80 ° C for 2 hours to stop the reaction and remove the solvent , adding 200 mL of absolute ethanol, stirring and heating to reflux, a white powdery solid was precipitated, filtered, washed with 20 mL of ether, and dried to obtain 3.87 g of carnosine product, yield: 88%. Hydrazine was not detected in the product.

Embodiment 2

[0025] Add 14.2 g (4 mmol) of phthaloyl-L-carnosine, 14 mL of methylamine ethanol solution (27-30%, mass ratio) and 350 mL of absolute ethanol into a 500 mL reaction flask, and heat to reflux for 1 hour. Filtrate hot, wash with 2×80 mL of absolute ethanol, wash with 2×80 mL of ether, and dry to obtain 8.02 g of carnosine product with a yield of 89%. Hydrazine was not detected in the product.

Embodiment 3

[0027] Add 3.56 g (1 mmol) of phthaloyl-L-carnosine, 30 mL of isopropanol and 4 mL of methylamine aqueous solution (30%, mass ratio) to a 100 mL reaction flask, heat to reflux for 1.5 h, and heat filter, 2×80 mL Wash with absolute ethanol, wash with 2×80 mL ether, and dry to obtain 1.68 g of carnosine product, with a yield of 74%.

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Abstract

The invention relates to a preparation method of L-carnosine. According to the invention, phthaloyl-L-carnosine and organic amine are heated in a solvent, such that protective groups are removed and a product is precipitated; filtering, solvent washing, and drying are carried out, such that an L-carnosine product is obtained; or concentration, crystallization, filtering and drying are carried out, such that a hydrazine-free L-carnosine product is obtained. The method provided by the invention has the advantages of simple method, low cost, and high operability. No toxic compound hydrazine exists in the obtained carnosine product. The quality of the obtained product can be sufficiently ensured, and the health safety of the product is shown.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and in particular relates to a preparation method of L-carnosine. Background technique [0002] L-carnosine (English name: L-Carnosine, CAS No.: 305-84-0) was first detected in beef by Russian scientists Gulewitsh and Amiradzibi in 1900. It is found in mammalian brain, muscle and other tissues with nerve distribution Widely present in the animal body, its concentration is about 1-20mmol.L -1 , especially in chicken breast meat, the content is particularly high. In organisms, it is synthesized by carnosine synthase using β-alanine and L-histidine. The chemical name is β-alanyl-L-histidine, and its chemical structure is as follows: [0003] [0004] L-carnosine can participate in and regulate various physiological activities of the human body. It has excellent natural anti-oxidation, scavenging free radicals, chelating with transition metals, neuroprotection, promoting wou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64
CPCY02P20/55
Inventor 赵新齐巧艳计国桢陆建刚邢健
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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