| Identification | More | [Name]
S-Methyl-L-cysteine | [CAS]
1187-84-4 | [Synonyms]
H-CYS(ME)-OH
H-L-CYS(ME)-OH
(R)-2-AMINO-3-(METHYLMERCAPTO)PROPIONIC ACID
S-METHYL-CYSTEINE
S-METHYL-L-CYSTEINE
Alanine, 3-(methylthio)-, L-
L-CH3SCH2CH(NH2)COOH
L-Cysteine, S-methyl-
Methylcysteine
SMC
DL-S-Methyl-cysteine
S-Methyl-L-cysteine, 99+%
S-Methyl-L-Cysteine(SMC)
S-Methyl-L-Cys-OH
S-METHYL-L-CYSTEINE/ H-CYS(ME)-OH
(2R)-2-Amino-3-methylsulfanylpropanoic acid | [EINECS(EC#)]
214-701-6 | [Molecular Formula]
C4H9NO2S | [MDL Number]
MFCD00002612 | [Molecular Weight]
135.18 | [MOL File]
1187-84-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light beige fine crystalline powder | [Melting point ]
~240 °C (dec.) | [alpha ]
-29.5 º (c=1,water) | [Boiling point ]
300.3±37.0 °C(Predicted) | [density ]
1.149 (estimate) | [refractive index ]
-30 ° (C=2, H2O) | [storage temp. ]
−20°C
| [solubility ]
Aqueous Acid (Slightly, Sonicated), Aqueous Base (Sparingly, Sonicated) | [form ]
Solid | [pka]
pK1:8.97 (25°C) | [color ]
White to Off-White | [BRN ]
1721675 | [Major Application]
peptide synthesis | [InChI]
InChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1 | [InChIKey]
IDIDJDIHTAOVLG-VKHMYHEASA-N | [SMILES]
C(O)(=O)[C@H](CSC)N | [LogP]
0.380 (est) | [CAS DataBase Reference]
1187-84-4(CAS DataBase Reference) | [NIST Chemistry Reference]
s-Methyl-L-cysteine(1187-84-4) |
| Hazard Information | Back Directory | [Chemical Properties]
white to light beige fine crystalline powder | [Uses]
S-Methyl-L-cysteine is a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA). It has been studied as a theurapeutic for neurodegenerative diseases including Parkinson′s. | [Definition]
ChEBI: A cysteine derivative that is L-cysteine in which the hydrogen attached to the sulfur is replaced by a methyl group. | [Biological Activity]
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 garliccabbageand turnips and has been studied as a theurapeutic for neurodegenerative diseases including Parkinsonμs.
When used as a dietary supplement in the Drosphilia model of PDSMLC increases the efficacy of the MRSA catalytic antioxidant system by providing additional substrate available leading to increased resistance to oxidative stress. | [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.] |
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