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638-23-3

Basic Information
CAS No.: 638-23-3
Name: Carbocistein
Article Data: 21
Molecular Structure:
Molecular Structure of 638-23-3 (Carbocistein)
Formula: C5H9NO4S
Molecular Weight: 179.197
Synonyms: Alanine,3-[(carboxymethyl)thio]-, L- (6CI,8CI);(2R)-2-Amino-3-[(carboxymethyl)thio]propionic acid;(L)-2-Amino-3-(carboxymethylthio)propionicacid;(R)-S-(Carboxymethyl)cysteine;3-[(Carboxymethyl)thio]-L-alanine;AHR3053;Bronchokod;Carbocysteine;Chilvax;L-(Carboxymethyl)cysteine;LJ 206;Lisil;Lisomucil;Loviscol;Muciclar;Mucocis;Mucodyne;Mucofan;Mucolase;Mucolex;Pectox;Pulmoclase;Reomucil;Rhinathiol;Rhinatiol;S-(Carboxymethyl)-(R)-cysteine;Siroxyl;Thiodril;Transbronchin;L-Carbocysteine(S-CMC);
EINECS: 211-327-5
Density: 1.514 g/cm3
Melting Point: 208-213 °C (dec.)
Boiling Point: 417.3 °C at 760 mmHg
Flash Point: 206.2 °C
Solubility: soluble in cold water
Appearance: white to slightly off-white amorphous powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36-26
PSA: 125.92000
LogP: -0.08360
Synthetic route
10318-18-0

DL-cysteine hydrochloride

638-23-3

carbocisteine

Conditions
ConditionsYield
With Iodoacetic acid100%

L-cysteine hydrochloride

79-11-8

chloroacetic acid

638-23-3

carbocisteine

Conditions
ConditionsYield
With ammonia; sodium carbonate; sodium sulfite In water at 55℃; for 0.5h; pH=3 - 7.3; pH-value; Concentration; Reagent/catalyst; Temperature;96.7%
52-89-1

l-cysteine hydrochloride

79-11-8

chloroacetic acid

638-23-3

carbocisteine

Conditions
ConditionsYield
With ammonia; ammonium bicarbonate In water at 20 - 50℃; for 0.5h; pH=7.5; Reagent/catalyst; Temperature; pH-value; Large scale;96%
52-90-4

L-Cysteine

64-69-7

Iodoacetic acid

638-23-3

carbocisteine

Conditions
ConditionsYield
in schwach alkalischer oder neutraler wss. Loesung;
In water at 20℃; for 0.25h;
52-90-4

L-Cysteine

79-11-8

chloroacetic acid

638-23-3

carbocisteine

Conditions
ConditionsYield
in schwach alkalischer oder neutraler wss. Loesung;
56-89-3

L-cystine

79-11-8

chloroacetic acid

638-23-3

carbocisteine

Conditions
ConditionsYield
With sodium hydroxide; zinc at 30℃;
With sodium amide In ammonia
With ammonia; sodium
3926-62-3

sodium monochloroacetic acid

2150-55-2

2-amino-(2)-thiazoline-4-carboxylic acid

638-23-3

carbocisteine

Conditions
ConditionsYield
at 26℃; for 8h; potassium phosphate buffer pH 8.0, Pseudomonas desmolitica AJ 11898;
52-90-4

L-Cysteine

68-11-1

mercaptoacetic acid

638-23-3

carbocisteine

Conditions
ConditionsYield
With Tris-HCl buffer at 30℃; for 0.166667h; β-cyano-L-alanine synthase (from Spinacia oleracea, Chenopodiaceae);
With Tris-HCl buffer; β-cyano-L-alanine synthase (from Spinacea oleracea, Chenopodiaceae) at 30℃; for 0.166667h;
2731-73-9

2-amino-3-chloropropanoic acid

68-11-1

mercaptoacetic acid

638-23-3

carbocisteine

Conditions
ConditionsYield
With potassium phosphate; pyridoxal 5'-phosphate In water at 37℃; for 24h; enzyme catalyst: S-carboxymethyl-L-cysteine synthase from Escherichia coli W3110;
5147-00-2

O-acetyl-L-serine

68-11-1

mercaptoacetic acid

638-23-3

carbocisteine

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Chemistry

IUPAC Name: 2-Amino-3-(carboxymethylsulfanyl)propanoic acid
Carbocisteine's Molecular formula: C5H9NO4
Carbocisteine's Molar mass: 179.195 g/mol
EINECS: 211-327-5
alpha: -31o (c=1, 10% NaH2CO3)
storage temp.: 2-8°C
Water Solubility of Carbocisteine (CAS NO.638-23-3): soluble in cold water
Synonyms: (l)-2-amino-3-(carboxymethylthio)propionicacid;(r)-s-(carboxymethyl)cysteine;carbocisteine;l.j.206;l-3-((carboxymethyl)thio)alanine;l-carboxymethylcysteine;rhinathiol;rinatiol  
Index of Refraction: 1.588
Surface Tension: 78 dyne/cm
Melting point: 208-213 °C (dec.)
Density: 1.514 g/cm3
Flash Point: 206.2 °C
Enthalpy of Vaporization: 73.57 kJ/mol
Boiling Point: 417.3 °C at 760 mmHg
Vapour Pressure: 3.91E-08 mmHg at 25 °C 
Appearance of Carbocisteine (CAS NO.638-23-3): white to slightly off-white amorphous powder

Uses

 Carbocisteine (CAS NO.638-23-3) is an expectorant that can be used to help relieve the symptoms of Chronic Obstructive Pulmonary Disorder COPD and bronchiectasis by allowing the sufferer to bring up sputum more easily.

Toxicity Data With Reference

1.    

ipr-rat LD50:7800 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),190.
2.    

scu-rat LD50:10,300 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),190.
3.    

orl-mus LD50:8400 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),190.
4.    

ipr-mus LD50:1433 mg/kg

    YKKZAJ    Yakugaku Zasshi. Journal of Pharmacy. 94 (1974),1419.
5.    

scu-mus LD50:9 g/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),190.

6.  RTECS  AY4342000
RTECS#: CAS# 638-23-3: AY4342000
LD50/LC50: RTECS:
CAS# 638-23-3: Oral, mouse: LD50 = 8400 mg/kg;
Oral, rat: LD50 = >15 gm/kg;
Carcinogenicity: S-Carboxymethyl-L-cysteine - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
Other: The toxicological properties have not been fully investigated. See actual entry in RTECS for complete information.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.
Hazard Codes: IrritantXi
WGK Germany: 2
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25:Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.

Specification

Chemical Stability: Stable under normal temperatures and pressures.
Conditions to Avoid: Incompatible materials.
Incompatibilities with Other Materials Strong oxidizing agents.
Hazardous Decomposition Products Carbon monoxide, carbon dioxide.
Hazardous Polymerization Hazardous Polymerization