methyl (2R)-2-amino-3-sulfanylpropanoate hydrochloride

• ChemBase ID: 70134
• Molecular Formular: C4H10ClNO2S
• Molecular Mass: 171.6457
• Monoisotopic Mass: 171.01207725
• SMILES: C(=O)([C@@H](N)CS)OC.Cl
• Canonical SMILES: COC(=O)[C@H](CS)N.Cl
• InChI: InChI=1S/C4H9NO2S.ClH/c1-7-4(6)3(5)2-8;/h3,8H,2,5H2,1H3;1H/t3-;/m0./s1
• InChIKey: WHOHXJZQBJXAKL-DFWYDOINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-2-amino-3-sulfanylpropanoate hydrochloride
• IUPAC Traditional name: cysteine methyl ester hydrochloride
• Synonyms: L-Cysteine Methyl Ester Hydrochloride; (R)-Cysteine Methyl Ester Hydrochloride; LJ 48; Methyl (R)-2-Amino-3-mercaptopropanoate Hydrochloride; Methyl L-Cysteinate Hydrochloride; Methyl Cysteine Hydrochloride; Methyl α-Amino-β-mercaptopropionate Hydrochloride; Methyl β-Mercaptoalanine Hydrochloride; NSC 161611; Pectite; Visclair; Zeotin; Mecysteine Hydrochloride; L-Cysteine methyl ester hydrochloride; Mecystein HCl; Acdrile; Actiol; Methyl cysteine HCl; L-Cysteine methyl ester hydrochloride; L-半胱氨酸甲酯 盐酸盐

Database IDs

• CAS Number: 18598-63-5
• EC Number: 242-435-0
• MDL Number: MFCD00038985
• Beilstein Number: 3685824
• PubChem SID: 162035859; 24865699
• PubChem CID: 2733208

CALCULATED PROPERTIES

• Acid pKa: 9.958875
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.9473101
• LogD (pH = 7.4): -0.5501284
• Log P: -0.3842653
• Molar Refractivity: 32.9927 cm^3
• Polarizability: 13.479212 Å^3
• Polar Surface Area: 52.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~140 °C; 140-141°C (dec.); 142 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -1.8°, c = 10 in methanol; [α]20/D -2.1±0.2°, c = 10% in methanol

Safety Information

• Storage Condition: 0°C
• Storage Warning: IRRITANT
• RTECS: HA2460000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (RT); 95+%; 98%
• Grade: puriss.
• Linear Formula: HSCH2CH(NH2)COOCH3 · HCl

DETAILS

MP Biomedicals - 02150750

Hydrochloride
Crystalline

Sigma Aldrich - 410209

Packaging
25 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 30160

Other Notes
Used e.g. in the synthesis of peptides1; Preparation of thiazolidine-4-carboxylates with carbonyl compounds2,3,4

Toronto Research Chemicals - M203100

A mucolytic. An effective drug for the treatment of liver failure. Shown to effectively inhibit the binding of ethynylestradiol metabolites to protein and nucleic acids.

REFERENCES

• Tsukamoto, T. et al.: Oyo Yakuri, 17, 825 (1979)
• Bolt, H. M. et al.: J. Steroid Biochem., 5, 179 (1979)
• Komatsu, H. et al.: Oyo Yakuri, 19, 709 (1979)