Identification | More | [Name]
L-Cysteine methyl ester hydrochloride | [CAS]
18598-63-5 | [Synonyms]
H-CYS(ME)OH HYDROCHLORIDE H-CYS-OME HCL L-CYSTEINE METHYL ESTER HYDROCHLORIDE L-CYSTEINE METHYL ESTER MONOHYDROCHLORIDE L-CYSTEIN METHYL ESTER HYDROCHLORIDE MECYSTEINE HYDROCHLORIDE methyl cysteine hydrochloride acdrile actiol l.j.48 methylester,hydrochloride,l-cystein pectite visclair zeotin L-Cysteine Methyl Ester HCl L-CYSTEINE METHYL ESTER HYDROCHLORIDECRY STALLINE L-CYSTEINE METHYL ESTER HYDROCHLORIDE, 9 8% Mecysteine HCL L-Cystein methyl ester HCl H-CYS(ME)-OH . HCL | [EINECS(EC#)]
242-435-0 | [Molecular Formula]
C4H10ClNO2S | [MDL Number]
MFCD00038985 | [Molecular Weight]
171.65 | [MOL File]
18598-63-5.mol |
Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
142 °C (dec.)(lit.)
| [alpha ]
-2.25 º (c=5, 1 N HCl) | [density ]
1.232 (estimate) | [FEMA ]
4781 | L-CYSTEINE METHYL ESTER HYDROCHLORIDE | [refractive index ]
-2.5 ° (C=20, MeOH) | [storage temp. ]
−20°C | [solubility ]
DMSO (Slightly), Methanol, Water (Slightly) | [form ]
Crystalline Powder | [color ]
White | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [biological source]
synthetic | [Optical Rotation]
[α]20/D 1.8°, c = 10 in methanol | [Water Solubility ]
Soluble in water | [Merck ]
13,5809 | [BRN ]
3685824 | [InChIKey]
WHOHXJZQBJXAKL-DFWYDOINSA-N | [CAS DataBase Reference]
18598-63-5(CAS DataBase Reference) |
Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
2
| [RTECS ]
HA2460000
| [F ]
1-10 | [HS Code ]
29309090 |
Hazard Information | Back Directory | [Chemical Properties]
white crystalline powder | [Uses]
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. | [Uses]
Mucolytic agent | [Definition]
ChEBI: Mecysteine hydrochloride is an alpha-amino acid ester. | [Preparation]
L-Cysteine methyl ester hydrochloride is prepared by esterification of L-cysteine hydrochloride monohydrate with methanol in the presence of hydrogen chloride.
| [reaction suitability]
reaction type: solution phase peptide synthesis | [Trade name]
Acthiol (Joullié, France), Actiol (Lirca, Italy), Visclair (Sinclair, UK), Aslos-C (Nissin, J), Epectan (Seiko, Japan), Moltanine (Tohok.-Tokyo Tanabe, Japan), Radcol (Nippon Universal, Japan), Sekinin (Tokyo Hosei, Japan).
| [Synthesis]
3 mL of sulfoxide chloride (SOCl2) was slowly added dropwise to 35 mL of methanol under nitrogen protection in an ice bath. Subsequently, the reaction mixture was stirred at room temperature for 1 hour. After that, 1 g of L-cysteine hydrochloride monohydrate (Cys-HCl-H2O) was added to the above solution in batches. The reaction was continued with the mixed solution at room temperature for 3 hours and then heated to reflux for 1 hour. Upon completion of the reaction, the volatile components and solvent were removed by distillation under reduced pressure, and the resulting residue was recrystallized using a solvent mixture of methanol-dichloromethane (CH3OH-CH2Cl2) to give 0.84 g of the white solid product L-cysteine methyl ester hydrochloride in 85.9% yield. The product was analyzed by infrared spectroscopy (IR, KBr press) showing characteristic absorption peaks: 3040.4 cm-1 (strong, NH2 stretching vibration), 1709.7 cm-1 (strong, C=O stretching vibration), 2580 cm-1 (weak, SH stretching vibration). The nuclear magnetic resonance hydrogen spectrum (1H NMR, D2O as solvent, TMS as internal standard) data were as follows: δ 4.453 (t, 1H, CH, J = 5.2 Hz), 3.871 (s, 3H, CH3), 3.164 (t, 2H, CH2, J = 6.4 Hz). Elemental analysis results: Calculated values (C4H10NO2SCCl): C, 27.99%; H, 5.87%; N, 8.16%. Measured values: C, 28.11%; H, 6.01%; N, 8.08%. | [storage]
Store at 2-8°C | [References]
[1] European Journal of Medicinal Chemistry, 2014, vol. 74, p. 199 - 215 [2] Journal of Organic Chemistry, 2013, vol. 78, # 9, p. 4270 - 4277 [3] Tetrahedron Asymmetry, 2000, vol. 11, # 21, p. 4255 - 4261 [4] Journal of the American Chemical Society, 2008, vol. 130, # 15, p. 5052 - 5053 [5] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 176 - 187,12 |
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