S-Methyl-L-cysteine

Names

[ Name ]:
S-Methyl-L-cysteine

[Synonym ]:
L-methylcysteine
(2R)-2-(Methylamino)-3-sulfanylpropanoic acid
S-METHYL-CYSTEINE
H-Cys(Me)-OH
SMC
Methylcysteine
DL-S-Methyl-cysteine
N-Methyl-L-cystein
Cysteine, N-methyl, L-
(R)-N-Methylcysteine
S-Methyl-L-cysteine
(2R)-2-amino-3-methylsulfanyl-propionic acid
EINECS 214-701-6
L-Cysteine, N-methyl-
L-Cysteine,S-methyl
N-Méthyl-L-cystéine
L-CH3SCH2CH(NH2)COOH
N-Methyl-L-cysteine
H-L-CYS(ME)-OH
MFCD00002612
(R)-2-Amino-3-(methylmercapto)propionic acid SMLC
S-Methyl-L-Cys-OH

Biological Activity

[Description]:

S-Methyl-L-cysteine is a natural product that acts as a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA), with antioxidative, neuroprotective, and anti-obesity activities.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

Natural Products >> Others

[In Vivo]

S-Methyl-L-cysteine (100 mg/kg) results in significant attenuation of plasma glucose, insulin, tumor necrosis factor-alpha, insulin resistance and improved antioxidant enzyme activities[1].

[References]

[1]. Thomas S, et al. Effect of s-methyl-L-cysteine on oxidative stress, inflammation and insulin resistance in male wistar rats fed with high fructose diet. Iran J Med Sci. 2015 Jan;40(1):45-50.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
242.8±30.0 °C at 760 mmHg

[ Melting Point ]:
~240 °C (dec.)

[ Molecular Formula ]:
C₄H₉NO₂S

[ Molecular Weight ]:
135.185

[ Flash Point ]:
100.7±24.6 °C

[ Exact Mass ]:
135.035400

[ PSA ]:
88.62000

[ LogP ]:
0.47

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.509

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S24/25-S36/37/39-S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Selective Allosteric Inhibition of MMP9 Is Efficacious in Preclinical Models of Ulcerative Colitis and Colorectal Cancer.

PLoS ONE 10 , e0127063, (2015)

Expression of matrix metalloproteinase 9 (MMP9) is elevated in a variety of inflammatory and oncology indications, including ulcerative colitis and colorectal cancer. MMP9 is a downstream effector and...

Cysteine amide adduct formation from carboxylic acid drugs via UGT-mediated bioactivation in human liver microsomes.

Pharmazie 70 , 678-83, (2015)

Although chemical trapping has been widely used to evaluate cytochrome P450-mediated drug bioactivation, thus far, only a few in vitro-trapping studies have been performed on UDP-glucuronosyltransfera...

Synthesis and biological evaluation of L-cysteine derivatives as mitotic kinesin Eg5 inhibitors.

Bioorg. Med. Chem. Lett. 17 , 3921-4, (2007)

Inhibition of Eg5 represents a novel approach for the treatment of cancer. Here, we report the synthesis and structure-activity relationship of S-trityl-L-cysteine (STLC) derivatives as Eg5 inhibitors...