5714-80-7

Basic information

• Product Name: methyl DL-cysteinate hydrochloride
• Synonyms: methyl DL-cysteinate hydrochloride;(±)-Cysteine methyl ester hydrochloride;DL-Cysteine methyl ester hydrochloride;Methyl 2-aMino-3-Mercaptopropionate hydrochloride;Methyl 2-amino-3-mercaptopropanoate hydrochloride, Methyl DL-cysteinate hydrochloride;Methyl 2-amino-3-mercaptopropanoate;Cysteine Methyl Ester Hydrochloride(1:1)
• CAS NO: 5714-80-7
• Molecular Formula: C₄H₁₀NO₂S*Cl
• Molecular Weight: 171.6457
• EINECS: 227-208-6
• Mol File: 5714-80-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 175-182 °C
• Boiling Point: 197.2°Cat760mmHg
• Flash Point: 73.1°C
• Appearance: /
• Density: g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: methyl DL-cysteinate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: methyl DL-cysteinate hydrochloride(5714-80-7)
• EPA Substance Registry System: methyl DL-cysteinate hydrochloride(5714-80-7)

Safety Data

• Hazardous Substances Data: 5714-80-7(Hazardous Substances Data)

Usage

General Description

Methyl DL-cysteinate hydrochloride is a chemical compound derived from the amino acid cysteine, which is commonly found in proteins and has important roles in metabolism and antioxidant defenses. The compound is used in various pharmaceutical and biotechnology applications, including as a precursor to the production of the antioxidant glutathione. It is also used as a chiral resolving agent and as a substrate in the production of cysteine-based drugs. Methyl DL-cysteinate hydrochloride has shown potential in research for its ability to protect against oxidative stress and its possible therapeutic roles in conditions involving cysteine metabolism and antioxidant imbalances. Overall, this compound has a range of potential applications in the pharmaceutical and biotechnology industries due to its diverse chemical properties and potential health benefits.

InChI:InChI=1/C4H9NO2S.ClH/c1-7-4(6)3(5)2-8;/h3,8H,2,5H2,1H3;1H

Upstream product

• 67-56-1 methanol 
• 921-01-7 rac-cysteine 
• 921-01-7 D-cysteine 
• 52-89-1 D-cysteine hydrochloride monohydrate 
• 32443-99-5 D-cysteine hydrochloride 

Downstream Products

• 125075-16-3 (2S,5R,7R)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid methyl ester 
• 109429-17-6 (2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid methyl ester 
• 109317-07-9 (2R,5S,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid methyl ester 
• 109317-05-7 (2Ξ,4S,2'S)-<2'-(benzyloxycarbonylaminopropanoic acid benzyl ester)>-3-aza-4-(methoxycarbonyl)tetrahydrothiophene 
• 3113-46-0 2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 443683-37-2 methyl (2S,4R)-2-benzoylthiazolidine-4-carboxylate 
• 443683-36-1 methyl (2R,4R)-2-benzoylthiazolidine-4-carboxylate 
• 42258-90-2 (R)-thiazolidine-4-carboxylic acid methyl ester 
• 302577-89-5 (R)-3-methoxycarbonyl-1-thia-4-azaspiro[4.5]decane 
• 69739-32-8 (2S,4R)-4-methoxycarbonyl-2-phenyl-1,3-thiazolidine 
• 69739-20-4 (2R,4R)-4-methoxycarbonyl-2-phenyl-1,3-thiazolidine 
• 5673-89-2 N-benzoyl-L-cysteine dimethyl ester 
• 111197-46-7 (3S,6S)-6-(Benzyloxycarbonyl-hydroxymethyl-amino)-5-oxo-hexahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid methyl ester 
• 6436-58-4 methyl 2-methyl-4,5-dihydrothiazole-4-carboxylate 

Relevant articles and documents

Benzoxaborole Antimalarial Agents. Part 5. Lead Optimization of Novel Amide Pyrazinyloxy Benzoxaboroles and Identification of a Preclinical Candidate

Carboxamide pyrazinyloxy benzoxaboroles were investigated with the goal to identify a molecule with satisfactory antimalarial activity, physicochemical properties, pharmacokinetic profile, in vivo efficacy, and safety profile. This optimization effort discovered 46, which met our target candidate profile. Compound 46 had excellent activity against cultured Plasmodium falciparum, and in vivo against P. falciparum and P. berghei in infected mice. It exhibited good PK properties in mice, rats, and dogs. It was highly active against the other 11 P. falciparum strains, which are mostly resistant to chloroquine and pyrimethamine. The rapid parasite in vitro reduction and in vivo parasite clearance profile of 46 were similar to those of artemisinin and chloroquine, two rapid-acting antimalarials. It was nongenotoxic in an Ames assay, an in vitro micronucleus assay, and an in vivo rat micronucleus assay when dosed orally up to 2000 mg/kg. The combined properties of this novel benzoxaborole support its progression to preclinical development.

Cycloforskamide, a cytotoxic macrocyclic peptide from the sea slug Pleurobranchus forskalii

A macrocylic dodecapeptide, cycloforskamide, was isolated from the sea slug Pleurobranchus forskalii, collected off Ishigaki Island, Japan. Its planar structure was deduced by extensive NMR analyses and was further confirmed by MS/MS fragmentation analyses. Finally, the absolute configuration was determined by total hydrolysis and chiral-phase gas chromatographic analysis. This novel dodecapeptide contains three d-amino acids and three thiazoline heterocycles and exhibits cytotoxicity against murine leukemia P388 cells, with an IC 50 of 5.8 μM.

Discovery of 2-arylthiazolidine-4-carboxylic acid amides as a new class of cytotoxic agents for prostate cancer

To improve the selectivity and antiproliferative activity of previously reported serine amide phosphates (SAPs), we designed a new series of 4-thiazolidinone amides, in which the 4-thiazolidinone moiety was introduced as a phosphate mimic. However, these 4-thiazolidinone derivatives demonstrated less cytotoxicity in prostate cancer cells despite improved selectivity over RH7777 cells. To further optimize the thiazolidinone analogues in terms of cytotoxicity and selectivity, we made closely related structural modifications, which led us to the discovery of a new class of 2-arylthiazolidine-4-carboxylic acid amides. These compounds were potent cytotoxic agents with IC50 values in the low micromolar concentration range and demonstrated enhanced selectivity in receptor-negative cells compared to SAPs and 4-thiazolidinone amides.