M6626

S-Methyl-L-cysteine

substrate for methionine sulfoxide reductase A

• Synonym(s): (R)-2-Amino-3-(methylmercapto)propionic acid, SMLC
• Linear Formula: CH₃SCH₂CH(NH₂)CO₂H
• CAS Number: 1187-84-4
• Molecular Weight: 135.18
• Beilstein: 1721675
• EC Number: 214-701-6
• MDL number: MFCD00002612
• UNSPSC Code: 12352209
• eCl@ss: 32160406
• PubChem Substance ID: 24897098
• NACRES: NA.26

Properties

• Quality Level: 200
• form: powder
• technique(s): ligand binding assay: suitable
• application(s): peptide synthesis
• storage temp.: −20°C
• SMILES string: CSC[C@H](N)C(O)=O
• InChI: 1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
• InChI key: IDIDJDIHTAOVLG-VKHMYHEASA-N

Description

Application

• In-vitro antioxidant and anti-inflammatory potential along with p.o. pharmacokinetic profile of key bioactive phytocompounds of Snow Mountain Garlic: a comparative analysis vis-à-vis normal garlic.: This study examines the antioxidant and anti-inflammatory properties of S-Methyl-L-cysteine found in Snow Mountain Garlic, providing insights into its potential therapeutic applications (Kaur et al., 2024).


• Acidification and tissue disruption affect glucosinolate and S-methyl-l-cysteine sulfoxide hydrolysis and formation of amines, isothiocyanates and other organosulfur compounds in red cabbage (Brassica oleracea var. capitata f. rubra).: The research highlights how acidification and tissue disruption influence the hydrolysis of S-Methyl-L-cysteine sulfoxide, impacting the formation of various bioactive compounds in red cabbage (Hanschen, 2024).


• Selective cycloaddition of ethylene oxide to CO(2) within the confined space of an amino acid-based metal-organic framework.: This research explores the use of an S-Methyl-L-cysteine-based metal-organic framework for the selective cycloaddition of ethylene oxide to CO₂, demonstrating its potential in green chemistry and materials science (Bilanin et al., 2023).

Biochem/physiol Actions

S-Methyl-L-cysteine (SMLC) is a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA). SMLC is naturally present in garlic, cabbage, and turnips and has been studied as a theurapeutic for neurodegenerative diseases including Parkinson′s.
When used as a dietary supplement in the Drosphilia model of PD, SMLC increases the efficacy of the MRSA catalytic antioxidant system by providing additional substrate available leading to increased resistance to oxidative stress.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves