1187-84-4

Basic information

• Product Name: S-Methyl-L-cysteine
• Synonyms: (R)-2-AMINO-3-(METHYLMERCAPTO)PROPIONIC ACID;S-METHYL-CYSTEINE;S-METHYL-L-CYSTEINE;H-L-CYS(ME)-OH;H-CYS(ME)-OH;Alanine, 3-(methylthio)-, L-;L-CH3SCH2CH(NH2)COOH;L-Cysteine, S-methyl-
• CAS NO: 1187-84-4
• Molecular Formula: C₄H₉NO₂S
• Molecular Weight: 135.18
• EINECS: 214-701-6
• Product Categories: Amino Acids Derivatives;Cysteine [Cys, C];Amino Acids and Derivatives;Amino Acid Derivatives
• Mol File: 1187-84-4.mol
• Article Data: 28

Chemical Properties

• Melting Point: ~240 °C (dec.)
• Boiling Point: 300.3 °C at 760 mmHg
• Flash Point: 135.4 °C
• Appearance: white to light beige fine crystalline powder
• Density: 1.149 (estimate)
• Vapor Pressure: 0.011mmHg at 25°C
• Refractive Index: -30 ° (C=2, H2O)
• Storage Temp.: −20°C
• Solubility: Aqueous Acid (Slightly, Sonicated), Aqueous Base (Sparingly, Sonicated), Water (
• PKA: pK1:8.97 (25°C)
• BRN: 1721675
• CAS DataBase Reference: S-Methyl-L-cysteine(CAS DataBase Reference)
• NIST Chemistry Reference: S-Methyl-L-cysteine(1187-84-4)
• EPA Substance Registry System: S-Methyl-L-cysteine(1187-84-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25-36/37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 1187-84-4(Hazardous Substances Data)

Usage

Description

S-Methyl-L-cysteine is a cysteine derivative in which the hydrogen atom attached to the sulfur atom of L-cysteine is replaced by a methyl group. It is a white to light beige fine crystalline powder and serves as a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA).

Uses

Used in Pharmaceutical Industry:
S-Methyl-L-cysteine is used as a therapeutic agent for neurodegenerative diseases, particularly for conditions such as Parkinson's disease. It plays a role in the catalytic antioxidant system, which may help in the treatment and management of these diseases.
Used in Antioxidant Systems:
S-Methyl-L-cysteine is used as a substrate in the methionine sulfoxide reductase A (MSRA) mediated antioxidant system. This system helps protect cells from oxidative stress and damage, which is crucial for maintaining cellular health and function.

Purification Methods

Likely impurities are cysteine and S-methyl-dl-cysteine. Crystallise it from H2O by adding 4volumes of EtOH. It also crystallises from MeOH with m 234-236o(dec), but after sublimation i t has m 267-270o and [] 27D -31.6o (c 1, H2O). [Rinderknecht et al. Helv Chim Acta 41 1, 10 1958, Theodoropoulos Acta Chem Scand 13 383 1959, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 1904 1961, Beilstein 4 IV 3145.]

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

Upstream product

• 52-90-4 L-Cysteine 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 56-89-3 L-cystine 
• 74-93-1 methylthiol 
• 2731-73-9 2-amino-3-chloropropanoic acid 
• 5147-00-2 O-acetyl-L-serine 
• 64969-77-3 hexadecyl-dimethylsulphonium iodide 
• 50-89-5 (+/-)-thymidine 
• 52-89-1 l-cysteine hydrochloride 
• 56-45-1 L-serin 
• 3981-36-0 3-chloro-DL-alanine 
• 21593-77-1 S-allyl cysteine 
• 16637-59-5 DL-N-acetyl-S-methylcysteine 

Downstream Products

• 3226-62-8 S-methyl-L-cysteine (R)-sulfoxide 
• 6853-87-8 methiin 
• 16637-59-5 (2R)-2-acetylamino-3-methylthiopropionic acid 
• 81251-82-3 N-(2,4-dinitro-phenyl)-S-methyl-L-cysteine 
• 3830-10-2 methyl (R)-2-amino-3-methylthiopropanoate 
• 69977-56-6 (R)-2-amino-3-(methylthio)propan-1-ol 
• 95406-97-6 N-[(benzyloxy)carbonyl]-S-methyl-L-cysteine 
• 34017-27-1 S-methyl-L-cysteine methyl ester hydrochloride salt 
• 100-61-8 N-methylaniline 
• 110949-44-5 (R)-2-(2-Benzoylsulfanyl-propionylamino)-3-methylsulfanyl-propionic acid 
• 87123-05-5 N-(2-benzylthio-2-methylpropanoyl)-S-methyl-L-cysteine 
• 88389-22-4 (R)-3-Methylsulfanyl-2-(2-methylsulfanylmethyl-3-phenyl-propionylamino)-propionic acid 
• 88389-20-2 N-<2-benzyl-3-(ethylthio)propanoyl>-S-methyl-L-cysteine 
• 88389-30-4 N-<3-(benzoylthio)-2-benzylpropanoyl>-S-methyl-L-cysteine 

Relevant articles and documents

Asymmetric synthesis of (S,R)- and (R,R)-methiin stereoisomers

An asymmetric synthesis of (+)- and (–)-methiine (S-methyl-(R)-cysteine sulfoxide) diastereomers has been developed. These natural sulfur compounds were isolated from a variety of Brassica vegetables. As the starting compound, (R)-cysteine was used, which was methylated to form (R)-S-methylcysteine. Then the oxidation of S-methylcysteine with tert-butyl hydroperoxide catalyzed by the chiral tetra(isopropylate)titanium/(S)- or (R)-Binol complex led to the formation of (1 R,2S)-(+)- or (1 R,2R)-(–)-methiin stereomers.

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Direct monitoring of biocatalytic deacetylation of amino acid substrates by1H NMR reveals fine details of substrate specificity

Amino acids are key synthetic building blocks that can be prepared in an enantiopure form by biocatalytic methods. We show that thel-selective ornithine deacetylase ArgE catalyses hydrolysis of a wide-range ofN-acyl-amino acid substrates. This activity was revealed by1H NMR spectroscopy that monitored the appearance of the well resolved signal of the acetate product. Furthermore, the assay was used to probe the subtle structural selectivity of the biocatalyst using a substrate that could adopt different rotameric conformations.

Composition for promoting differentiation of skin keratinocyte comprising a SAC derivatives or a SMC derivatives

The present invention relates to a composition for promoting keratinocyte differentiation. More specifically, SAC derivative or SMC derivatives as an active ingredient promotes differentiation of keratinocytes to promote skin keratinocyte differentiation, has excellent anti-wrinkling effect, skin barrier recovery effect, and is applicable to pharmaceutical, cosmetic, soap, body, shampoo and pack.