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638-23-3

638-23-3 Structure

638-23-3 Structure
IdentificationMore
[Name]

Carbocistein
[CAS]

638-23-3
[Synonyms]

3-[(CARBOXYMETHYL)THIO]ALANINE
3-CARBOXYMETHYLTHIO-L-ALANINE
CARBOCYSTEINE
CARBOXYMETHYLCYSTEINE
CARBOXYMETHYL-L-CYSTEINE
H-CYS(CARBOXYMETHYL)-OH
H-L-CYS(ACOH)-OH
L-CYSTEINE, S-(CARBOXYMETHYL)-
(R)-2-AMINO-3-(CARBOXYMETHYLTHIO)PROPIONIC ACID
(l)-2-amino-3-(carboxymethylthio)propionicacid
(r)-s-(carboxymethyl)cysteine
carbocisteine
l.j.206
l-3-((carboxymethyl)thio)alanine
l-carboxymethylcysteine
rhinathiol
rinatiol
s-(carboxymethyl)-(r)-cysteine
s-(carboxymethyl)-l-cystein
s-carboxylmethyl-l-cysteine
[EINECS(EC#)]

211-327-5
[Molecular Formula]

C5H9NO4S
[MDL Number]

MFCD00002614
[Molecular Weight]

179.19
[MOL File]

638-23-3.mol
Chemical PropertiesBack Directory
[Appearance]

white to slightly off-white amorphous powder
[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)
[form ]

Amorphous Powder
[pka]

2.06±0.10(Predicted)
[color ]

White to slightly off-white
[Water Solubility ]

SOLUBLE IN COLD WATER
[Merck ]

14,1802
[BRN ]

1725012
[Major Application]

pharmaceutical (small molecule)
[Cosmetics Ingredients Functions]

ANTI-SEBUM
SKIN CONDITIONING
[InChI]

1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
[InChIKey]

GBFLZEXEOZUWRN-VKHMYHEASA-N
[SMILES]

N[C@@H](CSCC(O)=O)C(O)=O
[LogP]

0.204 (est)
[Uses]

carbocysteine is an amino acid. It can be used to help control sebum production.
[CAS DataBase Reference]

638-23-3(CAS DataBase Reference)
[EPA Substance Registry System]

638-23-3(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Corrosion (GHS05)
GHS05
[Signal word ]

Danger
[Hazard statements ]

H314
[Precautionary statements ]

P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

2
[RTECS ]

AY4342000
[TSCA ]

Yes
[HS Code ]

29309090
[Storage Class]

11 - Combustible Solids
[Safety Profile]

contact. A riot control agent. When heated
[Toxicity]

LD50 oral in rat: > 15gm/kg
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Chloroacetic acid-->Sodium metabisulfite-->L-Cysteine-->L-Cysteine monohydrochloride-->S-Carboxymethyl-L-cysteine-->Sodium
[Preparation Products]

carbocysteine sulfoxide-->N-acetyl-S-(2-carboxymethyl)cysteine
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

3-Carboxymethylthio-L-alanine(638-23-3).msds
Hazard InformationBack Directory
[Chemical Properties]

white to slightly off-white amorphous powder
[Originator]

Rhinathiol,Kramer,Switz.
[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).
Spectrum DetailBack Directory
[Spectrum Detail]

S-Carboxymethyl-L-Cysteine(638-23-3)MS
S-Carboxymethyl-L-Cysteine(638-23-3)IR1
S-Carboxymethyl-L-Cysteine(638-23-3)IR2
S-Carboxymethyl-L-Cysteine(638-23-3)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

S-Carboxymethyl-L-cysteine, 98%(638-23-3)
[Alfa Aesar]

S-Carboxymethyl-L-cysteine, 97%(638-23-3)
[Sigma Aldrich]

638-23-3(sigmaaldrich)
[TCI AMERICA]

S-(Carboxymethyl)-L-cysteine,>98.0%(T)(638-23-3)
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