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

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

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

Downstream Products

• 100116-79-8 N-benzyloxycarbonyl-S-chloro-L-cysteine methyl ester 
• 198991-76-3 methyl (4R)-2-phenylthiazolidine-4-carboxylate 
• 6798-31-8 N,S-Bis-(2,2,2-trifluor-1-benzamino-ethyl)-L-cysteinmethylester 
• 2519-90-6 4-carbomethoxy-2-(4-nitrophenyl)-δ²-thiazoline 
• 58202-80-5 (R)-2-((Ξ)-1-benzyloxycarbonylamino-ethyl)-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 2564-58-1 (R)-2-(4'-hydroxyphenyl)-4-methoxycarbonyl-4,5-dihydrothiazole 
• 2519-89-3 (4R)-2-methyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester 
• 3113-46-0 2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 19547-88-7 methyl N,S-diacetylcysteinate 
• 18598-60-2 N,N'-ditrityl-L-cystine dimethyl ester 
• 96467-97-9 N-benzoyl-S-trityl-L-cysteine methyl ester 
• 236413-32-4 N,S-dibenzoyl-L-cysteine methyl ester 
• 2418-97-5 N,S-Bis-<2-nitro-phenyl-sulfenyl>-L-cystein-methyl-ester 
• 2518-12-9 (4R)-2-phenyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester 

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.

Redox-Driven Chiral Inversion of Water-Soluble Pillar[5]arene with l -Cystine Derivative in the Aqueous Medium

In the aqueous solution, l-CySS-OMe induced pS-WP5 from racemic WP5. Upon the addition of dithiothreitol as a reducing reagent to the above system, pS-WP5 was then converted to pR-WP5 for the reason that l-CySS-OMe was reduced to l-Cys-OMe. Followed by the addition of H2O2 as an oxidation reagent, pR-WP5 was converted back to pS-WP5. The chiral conformational transferring process between pR-WP5 and pS-WP5 can be easily and visually observed by reading the CD signal.

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.

Amino acid conjugates of 2-mercaptobenzimidazole provide better anti-inflammatory pharmacology and improved toxicity profile

Benzimidazole is an important pharmacophore for clinically active drugs against inflammation and treatment of pain, however, it is associated with gastrointestinal side effects. Here we synthesized benzimidazole based agents with significant analgesic/anti-inflammatory potential but with less gastrointestinal adverse effects. In this study, we synthesized novel, orally bioavailable 2-mercaptobenzimidazole amino acid conjugates (4a–4o) and screened them for analgesic, anti-inflammatory and gastro-protective effects. The synthesized 2-mercaptbenzimidazole derivatives were characterized for their structure using FTIR, 1H NMR and 13C NMR spectroscopic techniques. The 2-mercaptobenzimidazole amino acid conjugates have found to possess potent analgesic, anti-inflammatory and gastroprotective activities, particularly with compound 4j and 4k. Most of the compounds exhibited remarkable anti-ulcer and antisecretory effects. Molecular docking studies were carried out to study the binding affinities and interactions of the synthesized compounds with target proteins COX-2 (PDB ID: 3LN1) and H+/K+-ATPase (PDB ID: 5Y0B). Our results support the clinical promise of these newly synthesized 2-mercaptobezimidazol conjugates as a component of therapeutic strategies for inflammation and analgesia, for which the gastric side effects are always a major limitation.

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.

Synthetic Access to 3-Substituted Pyroglutamic Acids from Tetramate Derivatives of Serine, Threonine, allo-Threonine, and Cysteine

A general route which provides direct access to pyroglutamates from tetramates, making use of Suzuki coupling on an enol mesylate, followed by reduction, is reported. This work permits direct scaffold hopping from tetramate to substituted pyroglutamates. Some compounds in the library showed modest antibacterial activity against Gram-positive bacteria.

Synthetic access to 3,4-disubstituted pyroglutamates from tetramate derivatives from serine, allo-threonine and cysteine

A route allowing the conversion of substituted tetramates to 3,4-disubstituted pyroglutamates, making use of Suzuki coupling on an enol mesylate, followed by reduction, is both general and fully stereoselective.

Selective Photoredox Trifluoromethylation of Tryptophan-Containing Peptides

For application in drug discovery and biomedicine, it is crucial to develop new biocompatible methods to modify polypeptides. Herein, a visible-light-induced photoredox trifluoromethylation of tryptophan-containing peptides is reported. Under a mild, biocompatible, and straightforward condition, this strategy could incorporate the trifluoromethyl group into tryptophan residue with excellent chemo- and site-selectivity. The use of lower photocatalyst loading in 2 mol-% and cheap CF3SO2Na salt represents a great catalytic activity and economic CF3 source. This direct trifluoromethylation strategy allows the ready study of fluorinated peptides exploiting 19F-NMR. Additionally, the development of this protocol enables the study of biochemical systems and potentially modulates the function of biomolecules. Careful mechanistic studies (Stern-Volmer fluorescence quenching, EPR, and radical inhibition/trapping experiments) indicate that the reaction would proceed with a radical–radical cross-coupling procedure.

Purple acid phosphatase inhibitors as leads for osteoporosis chemotherapeutics

Purple acid phosphatases (PAPs) are metalloenzymes that catalyse the hydrolysis of phosphate esters under acidic conditions. Their active site contains a Fe(III)Fe(II) metal centre in mammals and a Fe(III)Zn(II) or Fe(III)Mn(II) metal centre in plants. In humans, elevated PAP levels in serum strongly correlate with the progression of osteoporosis and metabolic bone malignancies, which make PAP a target suitable for the development of chemotherapeutics to combat bone ailments. Due to difficulties in obtaining the human enzyme, the corresponding enzymes from red kidney bean and pig have been used previously to develop specific PAP inhibitors. Here, existing lead compounds were further elaborated to create a series of inhibitors with Ki values as low as ～30 μM. The inhibition constants of these compounds were of comparable magnitude for pig and red kidney bean PAPs, indicating that relevant binding interactions are conserved. The crystal structure of red kidney bean PAP in complex with the most potent inhibitor in this series, compound 4f, was solved to 2.40 ? resolution. This inhibitor coordinates directly to the binuclear metal centre in the active site as expected based on its competitive mode of inhibition. Docking simulations predict that this compound binds to human PAP in a similar mode. This study presents the first example of a PAP structure in complex with an inhibitor that is of relevance to the development of anti-osteoporotic chemotherapeutics.

A pyrroline ketone sulfur derivative and its preparation method and application

The invention belongs to the field of pesticide and plant protection and discloses pyrrolidone sulfur derivatives or their physiologically soluble salts. The pyrrolidone sulfur derivatives have a structural formula (I), wherein R=-(CH)nSCmHm, n is an integer of 1-7, m is an integer of 0-5, the case of n=2 and m=1 is excluded and the case of n=2 and m=2 is excluded. The invention also discloses a preparation method of the pyrrolidone sulfur derivatives or a use of the pyrrolidone sulfur derivatives in prevention and control of weeds. Compared with the original compound, the pyrrolidone sulfur derivatives or their physiologically soluble salts have higher weeding activity and a lower synthesis cost and can be stored easily. After contacting with the pyrrolidone sulfur derivative liquid, weeds produce cell death and brown disease spots at the contacting positions. The pyrrolidone sulfur derivative liquid can kill weeds usually in 3-5 days, has weeding broad spectrum activity, has small environmental pollution and less residue, has little activity after entering into solid in use, can be passivated fast and has very high environment safety.