S-Carboxymethyl-L-Cysteine Chemical Properties

Melting point:

208-213 °C (dec.)

alpha 

-31 º (c=1, 10% NaH2CO3)

Boiling point:

417.3±45.0 °C(Predicted)

Density 

1.315 (estimate)

refractive index 

1.5216 (estimate)

storage temp. 

2-8°C

solubility 

Aqueous Acid, Aqueous Base (Sparingly, Sonicated)

pka

2.06±0.10(Predicted)

form 

Amorphous Powder

color 

White to slightly off-white

Water Solubility 

SOLUBLE IN COLD WATER

Merck 

14,1802

BRN 

1725012

LogP

0.204 (est)

CAS DataBase Reference

638-23-3(CAS DataBase Reference)

EPA Substance Registry System

L-Cysteine, S-(carboxymethyl)- (638-23-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

2

RTECS 

AY4342000

TSCA 

Yes

HS Code 

29309090

Toxicity

LD50 oral in rat: > 15gm/kg

MSDS

• Language:English Provider:3-Carboxymethylthio-L-alanine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

S-Carboxymethyl-L-Cysteine Usage And Synthesis

Chemical Properties

white to slightly off-white amorphous powder

Originator

Rhinathiol,Kramer,Switz.

Uses

Carbocisteine is a mucolytic agent used in the treatment of respiratory disorders ranging from the influenza virus infection to chronic obstructive pulmonary disease (COPD).

Uses

Labeled Carbocisteine, intended for use as an internal standard for the quantification of Carbocisteine by GC- or LC-mass spectrometry.

Uses

carbocysteine is an amino acid. It can be used to help control sebum production.

Definition

ChEBI: S-carboxymethyl-L-cysteine is an L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a carboxymethyl group. It has a role as a mucolytic. It is a L-cysteine thioether and a non-proteinogenic L-alpha-amino acid. It is a conjugate acid of a S-carboxylatomethyl-L-cysteine(1-).

Manufacturing Process

There were placed 120g of L-cysteine (0.5 mol) in a 2 liter three-necked flask equipped with a stirrer thermometer and methanol/dry ice cooling and 1.5 liters of liquid ammonia were allowed to enter at -40°C. Then there were added under continuous cooling 50 g (2.17 mols) of sodium metal in portions of 1 to 2 g during the course of one hour. The end of the reaction was recognized by the continuation of the blue color. After the end of the reaction the excess sodium was destroyed by the addition of ammonium chloride and the ammonia vaporized at normal pressure. The residue was taken up in 500 ml of water and concentrated in a vacuum to 200 ml in order to remove residual ammonia, and again treated with 300 ml of water. The entire operations were carried out under a nitrogen atmosphere.
The aqueous solution of the disodium salt of L-cysteine obtained is then reacted at 20°C to 30°C under a nitrogen atmosphere in the course of 30 minutes with stirring with a solution of 104 g of chloroacetic acid (1.1 mols) and 4 g of sodium pyrosulfite in 200 ml of water. It is also allowed to post react for 15 minutes at 20°C, the solution clarified over activated carbon and the filtrate treated with 90 ml of concentrated hydrochloric acid to a pH of 2.5.
Thereby the S-carboxymethyl-L-cysteine precipitates out in crystalline form. The product is filtered off with suction, well stirred in 500 ml of water, again filtered with suction and dried in a vacuum at 70°C. The yield is 92% based on L-cysteine.

brand name

Loviscol (Wyeth-Ayerst); Mucofan (Wyeth-Ayerst).

Therapeutic Function

Mucolytic, Expectorant, Nasal antiinfective

Biochem/physiol Actions

S-Carboxymethyl-L-cysteine is studied as a small molecule mucoactive drug in vivo. These studies include analyzing the oxidative metabolism of S-carboxymethyl-L-cysteine by enzymes such as phenylalanine monooxygenase(s).

Safety Profile

contact. A riot control agent. When heated

S-Carboxymethyl-L-Cysteine(638-23-3)Related Product Information

• Carboxymethyl cellulose
• Sodium carboxymethyl cellulose
• L-Cysteine
• L-Alanine
• Carboxymethyl chitosan
• Sodium carboxyl methylstarch
• 3-(Methylseleno)-L-alanine
• CARBOXYMETHYLCELLULOSE CALCIUM
• S-2-Hydroxyethyl-L-cysteine
• Ethyl isocyanoacetate
• Benzyl isocyanide
• METHYL ISOCYANOACETATE
• TERT-BUTYL ISOCYANIDE
• 2,4-PENTANEDIONE, SILVER DERIVATIVE
• DICHLORO(ETHYLENEDIAMINE)PLATINUM(II)
• Carboxymethyl starch
• SALCOMINE
• COBALT(II) ACETYLACETONATE