18598-63-5

Basic information

• Product Name: L-Cysteine methyl ester hydrochloride
• Synonyms: Methyl α-aMino-β-Mercaptopropionate hydrochloride;Methyl β-Mercaptoalanine hydrochloride;L-Cysteine Methyl ester hydrochloride, 98% 25GR;L-Cysteine Methyl ester hydrochloride, 98% 5GR;(R)-Cysteine Methyl Ester Hydrochloride;Methyl (R)-2-AMino-3-Mercaptopropanoate Hydrochloride;Methyl L-Cysteinate Hydrochloride;NSC 161611
• CAS NO: 18598-63-5
• Molecular Formula: C₄H₁₀NO₂S*Cl
• Molecular Weight: 171.65
• EINECS: 242-435-0
• Product Categories: Amino Acids & Derivatives;Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Amino Acids Derivatives;Amino Acids;Cysteine [Cys, C];Amino Acids and Derivatives;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acid Derivatives;Cysteine/Cystine;Peptide Synthesis
• Mol File: 18598-63-5.mol
• Article Data: 41

Chemical Properties

• Melting Point: 142 °C (dec.)(lit.)
• Boiling Point: 197.2 °C at 760 mmHg
• Flash Point: 73.1 °C
• Appearance: White/Crystalline Powder
• Density: 1.232 (estimate)
• Vapor Pressure: 0.384mmHg at 25°C
• Refractive Index: -2.5 ° (C=20, MeOH)
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol, Water (Slightly)
• Water Solubility: Soluble in water
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 13,5809
• BRN: 3685824
• CAS DataBase Reference: L-Cysteine methyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Cysteine methyl ester hydrochloride(18598-63-5)
• EPA Substance Registry System: L-Cysteine methyl ester hydrochloride(18598-63-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• RTECS: HA2460000
• F: 1-10
• Hazardous Substances Data: 18598-63-5(Hazardous Substances Data)

Usage

Description

L-Cysteine methyl ester hydrochloride is a white crystalline powder with biochemical properties. It is a derivative of the amino acid L-cysteine, featuring a methyl ester group and a hydrochloride counterion. L-Cysteine methyl ester hydrochloride is known for its ability to inhibit the binding of ethynylestradiol metabolites to protein and nucleic acids, making it a versatile molecule with potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
L-Cysteine methyl ester hydrochloride is used as a mucolytic agent for the treatment of respiratory disorders characterized by excessive mucus production. Its mucolytic properties help in breaking down and thinning mucus, facilitating easier expectoration and improving respiratory function.
Used in Hepatology:
L-Cysteine methyl ester hydrochloride is used as an effective drug for the treatment of liver failure. Its hepatoprotective effects contribute to the maintenance of liver function and the regeneration of liver cells, providing support in managing liver-related conditions.
Used in Contraceptive Research:
L-Cysteine methyl ester hydrochloride is used as a research compound to study the binding of ethynylestradiol metabolites to protein and nucleic acids. This application aids in understanding the interactions between contraceptive hormones and biological macromolecules, potentially leading to the development of safer and more effective contraceptive methods.
Used in Biochemistry and Peptide Synthesis:
L-Cysteine methyl ester hydrochloride is used as a biochemical reagent in the synthesis of peptides. Its unique structure allows for the formation of peptide bonds through a variety of coupling reactions, making it a valuable component in the development of novel peptide-based drugs and therapeutics.
Used in Organic Chemistry:
L-Cysteine methyl ester hydrochloride is used as a synthetic building block in the preparation of thiazolidine-4-carboxylates with carbonyl compounds. These compounds have potential applications in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C4H9NO2S.ClH/c1-7-4(6)3(5)2-8;/h3,8H,2,5H2,1H3;1H/t3-;/m1./s1

Upstream product

• 67-56-1 methanol 
• 52-89-1 D-cysteine hydrochloride monohydrate 
• 921-01-7 D-cysteine 
• 921-01-7 rac-cysteine 
• 32854-09-4 L-cystine dimethyl ester dihydrochloride 
• 1447695-69-3 cycloforskamide 
• 52-89-1 l-cysteine hydrochloride 
• 52-90-4 L-Cysteine 
• 32443-99-5 D-cysteine hydrochloride 

Downstream Products

• 302577-84-0 (R)-methyl 2,2-diethylthiazolidine-4-carboxylate 
• 302577-89-5 (R)-3-methoxycarbonyl-1-thia-4-azaspiro[4.5]decane 
• 292073-45-1 methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate 
• 101924-70-3 (R)-methyl 2-(1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazole-4-carboxylate 
• 132402-74-5 2-<(S)-1-t-butyloxycarbonylamino-2-phenyl-ethyl>-4-methoxycarbonylthiazole 
• 216302-09-9 methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate 
• 239437-75-3 (2RS,4S)-2-<2(R)--2-benzyl-2-carboxyethyl>thiazolidine-4-carboxylic acid methyl ester 
• 251444-06-1 N-[(2'R,3'S)-4'-(tert-Butyldiphenylsilyloxy)-2',3'-methanobutanoyl]-(S)-cysteine methyl ester 
• 69739-32-8 (2S,4R)-4-methoxycarbonyl-2-phenyl-1,3-thiazolidine 
• 69739-20-4 (2R,4R)-4-methoxycarbonyl-2-phenyl-1,3-thiazolidine 

Relevant articles and documents

Chiral molecular recognition in monolayers of diastereomeric N-acylamino acid methyl esters at the air/water interface

This article continues our study of the effects of headgroup geometry and temperature on chiral recognition in the force-area isotherms, thermodynamics of spreading, and surface shear viscosities of monolayers and mixed monolayers of long-chain amino acid ester surfactants. N-Stearoyl - and lauroyl - derivatives of the methyl esters of cysteine, cystine, and threonine are compared to the previously-reported serine derivative. The structural points at issue are as follows: (a) the effects of replacing the hydroxyl group of serine with the thiol group of cysteine; (b) the effect of joining two cysteine groups through their sulfur atoms to produce the two-chain cystine surfactant; and (c) the effect of attaching a methyl group to the carbon bearing the hydroxyl group in stearoylserine methyl ester (SSME) to produce the bulkier stearoylthreonine methyl ester (STME). Comparison is first made for the melting point versus enantiomer composition of the crystals for each compound. In all four cases a racemate is formed. Next, the corresponding effects of enantiomeric composition versus the appropriate surface properties are presented and behavior similar to the melting point curves is seen, implying stereoselective behavior when the monolayers are in equilibrium with their crystals or quasicrystalline condensed surface phases. Diastereomeric effects were small, since meso-dilauroylcystine dimethyl ester (DLCDME) showed properties which were nearly identical to its D and L enantiomers, and the allo form of STME was similar to its enantiomers. All four compounds showed distinctly different force-area curves for their enantiomers versus their racemic mixtures, but the shapes of the curves and phase behavior (between liquid-expanded and liquid-condensed films) depended heavily on temperature. All force-area curves show hysteresis effects in the difference between the compression and expansion regions, indicating, as we have shown before, that relaxation of compressed monolayer states is slow and that the films are in metastable states. Phase behavior is an erratic function of headgroup and temperature. Also, there is no general pattern of whether racemates or enantiomers are most expanded. No crystals of quality sufficient for X-ray analysis could be grown, so rigorous interpretation of properties and behavior in terms of structure cannot be made. However, clear differences between the behavior of stearoylcysteine methyl ester (SCME) and SSME can be interpreted in terms of hydrogen bonding of the serine hydroxyl group to the water subphase. Furthermore, comparison of force-area curves for a series of diastereomeric mixtures of L-STME and L-allo-STME with D- and L-SSME suggests that the stereochemistry at the carbon between the ester and amide functions is primarily responsible for the stereoselectivity in the packing of STME films. Films of SCME were too condensed to allow a surface viscosity study, but those of DLCDME and STME exhibited Newtonian flow with essentially no stereoselectivity in their flow properties.

Bicyclic Lactams Derived from Serine or Cysteine and 2-Methylpropanal

Bicyclic lactams may be prepared from serine or cysteine and 2-methylpropanal; the resulting S, N -heterocycles are more stable than the corresponding O, N -heterocycles but both are synthetic intermediates capable of further elaboration.

Hydroxyphosphinylacetic acid as a chiral auxiliary compound

The aim of the presented research was to check whether 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid is a versatile chiral phosphonic auxiliary (readily seen in 31P NMR). The preliminary studies indicate that this compound may be used as chiral derivatizing agents for amines and alcohols, since the separation of selected examples of diastereomeric alcohols and amines in 31P NMR spectra was found to be satisfactory. The preliminary research about using this compound as a CSA are also promising.