13552-61-9

Basic information

• Product Name: 2-thiolhistidine
• Synonyms: DL-2-Histidinethiol;DL-2-Thiohistidine;DL-2-Thiolhistidine
• CAS NO: 13552-61-9
• Molecular Formula: C₆H₉N₃O₂S
• Molecular Weight: 187.22
• Mol File: 13552-61-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 376.3°Cat760mmHg
• Flash Point: 181.4°C
• Appearance: /
• Density: 1.52g/cm³
• Vapor Pressure: 1.06E-06mmHg at 25°C
• Refractive Index: 1.695
• PKA: 2.27±0.10(Predicted)
• CAS DataBase Reference: 2-thiolhistidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-thiolhistidine(13552-61-9)
• EPA Substance Registry System: 2-thiolhistidine(13552-61-9)

Safety Data

• Hazardous Substances Data: 13552-61-9(Hazardous Substances Data)

Usage

General Description

2-thiolhistidine is a naturally occurring chemical compound that is a derivative of the amino acid histidine. It contains a thiol group, which is a sulfur atom bonded to a hydrogen atom, and is found within the side chain of the histidine molecule. 2-thiolhistidine plays a crucial role in the formation of metal ion-binding sites in proteins and enzymes, and is involved in various biological processes in the body. It has been studied for its potential antioxidant and metal-chelating properties, as well as its ability to modulate cellular redox signaling and regulate the activity of certain enzymes. Research has also suggested that 2-thiolhistidine may have therapeutic potential for certain diseases and medical conditions, though further studies are needed to fully understand its biological effects and potential applications.

InChI:InChI=1/C6H9N3O2S/c7-4(5(10)11)1-3-2-8-6(12)9-3/h2,4H,1,7H2,(H,10,11)(H2,8,9,12)

Upstream product

• 645-35-2 L-histidine monohydrochloride 
• 507-09-5 tiolacetic acid 
• 71-00-1 L-histidine 
• 5934-29-2 L-histidine hydrochloride monohydrate 
• 333-20-0 potassium thioacyanate 
• 78397-05-4 L-2,5-diamino-4-oxopentanoic acid dihydrochloride 
• 89765-68-4 C₁₁H₁₇N₃O₄S 
• 1027163-92-3 C₁₆H₂₅N₃O₆S 
• 1392219-77-0 C₁₆H₂₅N₃O₆S 
• 20898-43-5 4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-imidazole-1-carboxylic acid tert-butyl ester 
• 17791-51-4 methyl (S)-3-<1-(1,1-dimethylethoxycarbonyl)-1H-imidazol-5-yl>-2-<(1,1-dimethylethoxycarbonyl)amino>propionate 
• 4467-54-3 l-histidine methyl ester dihydrochloride 
• 168292-00-0 methyl (S)-2-<(1,1-dimethylethoxycarbonyl)amino>-3-(2-mercapto-1H-imidazol-4-yl)propionate 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

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METHOD FOR THE SYNTHESIS OF 2-THIOHISTIDINE AND THE LIKE

Methods for the synthesis of 2-thiohistidine or a derivative thereof of the formula (I), or of a physiologically acceptable salt, a tautomer, a stereoisomer or a mixture of stereoisomers in any proportions thereof, from a compound of the formula (II) or a physiologically acceptable salt, a tautomer, a stereoisomer or a mixture of stereoisomers in any proportions thereof, by cleavage reaction in the presence of a thiol at a temperature higher than or equal to 60° C. The invention also relates to compounds of the formula (II) and a method for the synthesis thereof.

PROCESS FOR THE SYNTHESIS OF L-(+)-ERGOTHIONEINE

This invention relates to a novel process for the preparation of optically pure L-(+)-ergothioneine. The process for the chemical synthesis of L-ergothioneine comprises steps which consist of reacting L-histidine alkyl ester with an acid halide, chloroformate or pyrocarbonate in the presence of a base, hydrolysis of the alkyl-(S,Z)-2,4,5-triamidopent-4-enoate to obtain a (S)-alkyl 2,5-diamido-4-oxopentanoate, acid catalyzed hydrolysis of the (S)-alkyl 2,5-diamido-4-oxopentanoate followed by reaction with a metal thiocyanate to obtain the thiohistidine, protection of the sulfur of thiohistidine as the tert-butyl thioether, dialkylation of the primary amine to obtain a tertiary amine, quaternization of the tertiary amine, and removal of the protecting group to obtain the desired (S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trialkylammonio)propanoate (I). This process affords a better yield and is capable of practical application at large scale.