N-Acetyl-cysteine supplier

Name
N-Acetyl-L-cysteine
EINECS 210-498-3
CAS No. 616-91-1
Article Data45
CAS DataBase
Density 1.295 g/cm³
Solubility Soluble in water, ethanol, methanol, dimethyl sulfoxide, hot isopropyl alcohol, methyl acetate and ethyl acetate. Insoluble in chloroform and ether.
Melting Point 106-108 °C
Formula C₅H₉NO₃S
Boiling Point 407.678 °C at 760 mmHg
Molecular Weight 163.197
Flash Point 200.357 °C
Transport Information
Appearance White crystalline powder
Safety 22-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Sodium 2-acetamido-3-mercaptopropionate;Mucolytikum Lappe;Acetein;Fluatox;(2R)-2-acetamido-3-sulfanyl-propanoic acid;Fabrol;Fluibiotic;Flumicil;Airbron;Mucosolvin;Tixair;Fluimucetin;N- Acetyl -L- Cysteine;Brunac;Ac-Cys;N-Acetyl Cysteine;Acetyl-L-cysteine;(R)-N-Acetylcysteine;Mercapturic acid, (R)-;L-Acetylcysteine;Mucomyst (TN);Mucofilin;(2R)-2-acetamido-3-sulfanyl-propanoate;N-Acetyl-L-Cysteine(NAC);Mucomyst;L-Cysteine, N-acetyl-;N-Acetyl-L-cysteine;N-Acetylcysteine;Flumucetin;Mucolyticum;Respaire;Mercapturic acid;Acetylcysteine (JAN/USP);L-Cysteine,N-acetyl-;Sodium N-acetyl-L-cysteinate;Cysteine, N-acetyl-, L-;Broncholysin;Parvolex;Broncholysin (mucolytic);Fluimucil;L-Cysteine, N-acetyl-,;
PSA 105.20000
LogP -0.10360

Synthetic route

: 108-24-7
acetic anhydride

: 7048-04-6
L-cysteine hydrochloride monohydrate

: 616-91-1
N-acetylcystein

Conditions

Conditions	Yield
With sodium acetate In tetrahydrofuran; water at 10 - 60℃; for 37h; pH=4 - 5; Inert atmosphere;	85%

: 463-51-4
Ketene

: 56-89-3
L-cystine

: 616-91-1
N-acetylcystein

Conditions

Conditions	Yield
durch Erwaermen des Reaktionsprodukts mit Zink und Essigsaeure auf 50-60grad; Reinigung ueber das Kupfer(I)-Salz;

: 56-89-3
L-cystine

: 108-24-7
acetic anhydride

: 616-91-1
N-acetylcystein

Conditions

Conditions	Yield
With sodium hydroxide durch Erwaermen des Reaktionsprodukts mit Zink und Essigsaeure auf 50-60grad; Reinigung ueber das Kupfer(I)-Salz;

: 108-22-5
Isopropenyl acetate

: 52-90-4
L-Cysteine

: 616-91-1
N-acetylcystein

Conditions

Conditions	Yield
In water

: Sodium; (R)-2-methyl-4,5-dihydro-thiazole-4-carboxylate

: 616-91-1
N-acetylcystein

Conditions

Conditions	Yield
With hydrogenchloride

: 86124-83-6
N-Acetyl-S-<2-(4-ethoxycarbonylphenylsulfonyl)ethyl>cystein

A: 616-91-1
N-acetylcystein

B: 5535-48-8
PVS

Conditions

Conditions	Yield
With sodium hydroxide Ambient temperature; reaction times, various conc. of NaOH, add. of N-Acetyl-S-<2-(phenylsulfonyl)ethyl>-cystein;

: N-Acetyl-L-cysteine disulfide radical anion

: 616-91-1
N-acetylcystein

Conditions

Conditions	Yield
With water; dinitrogen monoxide at 22℃; Equilibrium constant; Rate constant; Irradiation; various pH;

: 60-24-2
2-hydroxyethanethiol

: 675587-70-9
Nα-acetyl-S-(2,4-dinitro-5-(dimethylaminomethyl)phenyl)-L-cysteine

A: 616-91-1
N-acetylcystein

B: N,N-dimethyl-2,4-dinitro-5-((2-hydroxyethyl)thio)benzylamine

Conditions

Conditions	Yield
With sodium phosphate buffer for 1h; pH=8.0;

...Expand

: 1222442-92-3
2-acetamido-3-(3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoylthio)propanoic acid

A: 616-91-1
N-acetylcystein

B: 16048-89-8, 921-28-8, 16048-77-4, 111408-27-6, 113473-21-5, 126576-14-5
2-hydroxy-3-isopropylbutanedioic acid

Conditions

Conditions	Yield
With water; sodium hydroxide at 40℃; for 1h;

: 72-18-4
L-valine

: 1415322-55-2
N-acetyl-S-[[4-(4-aminobenzyl)phenyl]carbamoyl]-cysteine

A: 616-91-1
N-acetylcystein

B: 1415322-26-7
N-([4-(4-aminobenzyl)-phenyl]carbamoyl)-valine

C: 1,3-bis{4-[4-aminobenzyl]-phenyl}urea

Conditions

Conditions	Yield
In aq. phosphate buffer at 37℃; for 5h; pH=7.4;

...Expand

: N-acetyl-DL-cysteine hydrochloride

A: 616-91-1
N-acetylcystein

B: 26117-28-2
(S)-N-acetylcysteine

Conditions

Conditions	Yield
With acetic acid In hexane; isopropyl alcohol at 25℃; Reagent/catalyst; Solvent; Resolution of racemate;

: 67-56-1
methanol

: 616-91-1
N-acetylcystein

: 7652-46-2
Ac-Cys-OMe

Conditions

Conditions	Yield
With acetyl chloride at 20℃; for 48h;	100%
With thionyl chloride In chloroform	90%
With thionyl chloride at 0 - 20℃; for 3h;	80.5%

: 616-91-1
N-acetylcystein

: 5545-17-5
N,N'-diacetyl-L-cystine

Conditions

Conditions	Yield
With bis(4-methoxyphenyl)telluride; 5,15,10,20-tetraphenylporphyrin In dichloromethane; isopropyl alcohol at 0℃; for 0.25h; Irradiation;	100%
With (bis(2,1-phenylene)bis(azanediyl)bis(methylene)diphenol)diselenide In water; acetonitrile at 20℃; for 7h;	83%
With (+)-flavinophane Fl(7) In methanol; water at 30℃; Rate constant; pH 9.55; other (+)- and (-)-flavinophanes and 5-deazaflavinophanes; asymmetric discrimination;

: 616-91-1
N-acetylcystein

: 675587-65-2
N,N-dimethyl-2,4-dinitro-5-fluorobenzylamine

: 675587-70-9
Nα-acetyl-S-(2,4-dinitro-5-(dimethylaminomethyl)phenyl)-L-cysteine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 20℃; for 0.5h; pH=7.0;	100%

: 616-91-1
N-acetylcystein

: 85363-04-8
tert-butyl cyanomethylcarbamate

: NH2CH2CNC5H8O2NH3*C3H7SNO2C2H2O

Conditions

Conditions	Yield
With ammonia In methanol at 60℃; for 7h;	100%

: 616-91-1
N-acetylcystein

: 1072807-15-8
phenylbutyl isoselenocyanate

: 1072807-17-0
C16H22N2O3SSe

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃;	100%

: 616-91-1
N-acetylcystein

: 61499-10-3
Phenylbutyl isothiocyanate

: C16H22N2O3S2

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃;	100%

: 616-91-1
N-acetylcystein

: 1229030-44-7
1-[2-(2-furanyl)-3-hydroxy-4-oxo-4H-1-benzopyran-6-yl]-1H-pyrrole-2,5-dione

: 1229030-45-8
AcCys-MCF

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	100%

: 616-91-1
N-acetylcystein

: 1233858-76-8
4-(5-phenyl-3-(selenocyanatomethyl)-1H-pyrazol-1-yl)benzenesulfonamide

: selenocoxib-1-N-aceylcysteine

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 12h;	100%

: 616-91-1
N-acetylcystein

: 133613-71-5
(4R,5aS,7aS,7bR)-5,5a,6,7,7a,7b-hexahydro-7b-hydroxy-4-methyl-indeno[1,7-bc]furan-2(4H)-one

: 3β-(N-acetyl L-cysteine)-2aβ,3-dihydrogaliellalactone

Conditions

Conditions	Yield
With triethylamine In d(4)-methanol for 24h;	100%

: 616-91-1
N-acetylcystein

: 76290-84-1
ethyl-(2-hydroxy-ethyl)-dimethyl-ammonium; hydroxide

: C6H16NO(1+)*C5H8NO3S(1-)

Conditions

Conditions	Yield
In water at 20℃;	100%

: 616-91-1
N-acetylcystein

: C7H18NO(1+)*HO(1-)

: C5H8NO3S(1-)*C7H18NO(1+)

Conditions

Conditions	Yield
In water at 20℃;	100%

: 616-91-1
N-acetylcystein

: 114380-13-1
butyl(2-hydroxyethyl)dimethylammonium hydroxide

: C5H8NO3S(1-)*C8H20NO(1+)

Conditions

Conditions	Yield
In water at 20℃;	100%

: 616-91-1
N-acetylcystein

: C9H22NO(1+)*HO(1-)

: C5H8NO3S(1-)*C9H22NO(1+)

Conditions

Conditions	Yield
In water at 20℃;	100%

: 616-91-1
N-acetylcystein

: 1204316-79-9
1,1,1-trioctyl-1-methylphosphonium methylcarbonate

A: trioctylmethylphosphonium 3-mercaptopropionate

B: C6H8O4S2(2-)*2C25H54P(1+)

Conditions

Conditions	Yield
In methanol at 25℃; for 2h;	A 100% B 12%

...Expand

: 75-15-0
carbon disulfide

: 616-91-1
N-acetylcystein

: 100-39-0
benzyl bromide

: 959855-27-7
2-acetamido-3-(benzylsulfanylthiocarbonylsulfanyl)propionic acid

Conditions

Conditions	Yield
Stage #1: N-acetylcystein With sodium methylate In methanol Stage #2: carbon disulfide In methanol Stage #3: benzyl bromide In methanol Further stages.;	99.2%

...Expand

: 591-50-4
iodobenzene

: 616-91-1
N-acetylcystein

: 4775-80-8
(R)-2-acetamido-3-(phenylthio)propanoic acid

Conditions

Conditions	Yield
Stage #1: iodobenzene; N-acetylcystein With C53H46NO4PPdS In tetrahydrofuran at 20℃; for 0.0166667h; Schlenk technique; Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; chemoselective reaction;	99%
With copper(l) iodide In N,N-dimethyl-formamide at 100℃; for 68h;	28%

: 616-91-1
N-acetylcystein

: 90-14-2
1-Iodonaphthalene

: 51325-34-9
(R)-2-acetamido-3-(naphthalen-1-ylthio)propanoic acid

Conditions

Conditions	Yield
Stage #1: N-acetylcystein; 1-Iodonaphthalene With C53H46NO4PPdS In tetrahydrofuran at 20℃; for 0.0166667h; Schlenk technique; Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; chemoselective reaction;	99%
With copper(l) iodide In N,N-dimethyl-formamide at 100℃; for 68h;	31%

: 616-91-1
N-acetylcystein

: 154226-60-5
omuralide

: Lactacystin

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 23℃; for 4h;	99%
With triethylamine In dichloromethane at 20℃; for 22h; Inert atmosphere;	87%
With triethylamine In dichloromethane at 20℃; for 14h;	79%

: 616-91-1
N-acetylcystein

: 107-02-8
acrolein

: 140226-30-8
S-(3-oxopropyl)mercapturic acid

Conditions

Conditions	Yield
In water at 20℃; Addition;	99%

: 6138-90-5
trans-geranyl bromide

: 616-91-1
N-acetylcystein

: 135784-50-8
N-acetyl-S-geranyl-L-cysteine

Conditions

Conditions	Yield
With sodium ethanolate In ethanol for 4h; Heating;	99%
With ammonia In methanol Alkylation;

: 616-91-1
N-acetylcystein

: 24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7
farnesyl bromide

: 135304-07-3
N-acetyl-S-trans,trans-farnesyl-L-cysteine

Conditions

Conditions	Yield
With ammonia In methanol for 16h;	99%
With ammonia In methanol Alkylation;

: 934499-56-6
1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]dodecane

: 616-91-1
N-acetylcystein

: L-2-(N-acetylamino)-3-(dodecyldisulfanyl)propionic acid

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.25h;	99%

: 1002347-30-9
1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]octadecane

: 616-91-1
N-acetylcystein

: (R)-2-(acetylamino)-3-(octadecyldisulfanyl)propanoic acid

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.25h;	99%

: (1,2-bis(2-mercaptophenylthio)ethane(PPh3)(N-acetyl-(L)methionine))ruthenium

: 616-91-1
N-acetylcystein

: (1,2-bis(2-mercaptophenylthio)ethane(PPh3)(N-acetyl-(L)methionine methylester))ruthenium

Conditions

Conditions	Yield
With hydrogenchloride In methanol To a suspn. of Ru-compd. gaseous HCl is added, mixt. is stirred for 24 h at room temp. (N2, without light).; Ppt. is filtered off, washed with MeOH/ether and ether, dried in high-vac., elem. anal.;	99%

: 616-91-1
N-acetylcystein

: C19H39PS3

: L-2-(N-acetylamino)-3-(dodecyldisulfanyl)propionic acid

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.25h;	99%

: 616-91-1
N-acetylcystein

: 624-31-7
4-tolyl iodide

: (R)-2-acetamido-3-(p-tolylthio)propanoic acid

Conditions

Conditions	Yield
Stage #1: N-acetylcystein; 4-tolyl iodide With C53H46NO4PPdS In tetrahydrofuran at 20℃; for 0.0166667h; Schlenk technique; Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; chemoselective reaction;	99%
With C51H42NOP2Pd(1+)*CH3O3S(1-); triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;	84%

: 637-87-6
1-Chloro-4-iodobenzene

: 616-91-1
N-acetylcystein

: 21462-48-6
(R)-2-acetamido-3-((4-chlorophenyl)thio)propanoic acid

Conditions

Conditions	Yield
Stage #1: 1-Chloro-4-iodobenzene; N-acetylcystein With C53H46NO4PPdS In tetrahydrofuran at 20℃; for 0.0166667h; Schlenk technique; Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; chemoselective reaction;	99%

: 616-91-1
N-acetylcystein

: 352-34-1
4-fluoro-1-iodobenzene

: 331-93-1
(R)-2-acetamido-3-((4-fluorophenyl)thio)propanoic acid

Conditions

Conditions	Yield
Stage #1: N-acetylcystein; 4-fluoro-1-iodobenzene With C53H46NO4PPdS In tetrahydrofuran at 20℃; for 0.0166667h; Schlenk technique; Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; chemoselective reaction;	99%

: 616-91-1
N-acetylcystein

: 589-87-7
1,4-bromoiodobenzene

: 21462-47-5
(R)-2-acetamido-3-((4-bromophenyl)thio)propanoic acid

Conditions

Conditions	Yield
Stage #1: N-acetylcystein; 1,4-bromoiodobenzene With C53H46NO4PPdS In tetrahydrofuran at 20℃; for 0.0166667h; Schlenk technique; Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; chemoselective reaction;	99%

: 616-91-1
N-acetylcystein

: 455-13-0
4-Iodobenzotrifluoride

: N-acetyl-S-(4-(trifluoromethyl)phenyl)-L-cysteine

Conditions

Conditions	Yield
Stage #1: N-acetylcystein; 4-Iodobenzotrifluoride With C53H46NO4PPdS In tetrahydrofuran at 20℃; for 0.0166667h; Schlenk technique; Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; chemoselective reaction;	99%

N-Acetyl-cysteine Consensus Reports

Reported in EPA TSCA Inventory.

N-Acetyl-cysteine Specification

1. Introduction of N-Acetyl-cysteine

N-Acetyl-cysteine, with the IUPAC Name of (2R)-2-acetamido-3-sulfanylpropanoic acid, is one kind of white crystalline powder. This product belongs to the Product Categories which include Phenylalanine analogs and other aromatic alpha amino acids; Amino; Amino Acids; Cysteine [Cys, C];Ac-Amino Acids; Amino Acids (N-Protected); Antioxidant; Biochemistry; Nutritional Supplements; Pharmaceutical Intermediates; N-Acetyl-Amino acid series; Miscellaneous Compounds.

2. Properties of N-Acetyl-cysteine

N-Acetyl-cysteine has the following property datas: (1)Freely Rotating Bonds: 4; (2)Polar Surface Area: 71.91 ?2; (3)Index of Refraction: 1.518; (4)Molar Refractivity: 38.25 cm3; (5)Molar Volume: 126 cm3; (6)Surface Tension: 49.9 dyne/cm; (7)Density: 1.294 g/cm3; (8)Flash Point: 200.4 °C; (9)Enthalpy of Vaporization: 72.37 kJ/mol; (10)Boiling Point: 407.7 °C at 760 mmHg; (11)Vapour Pressure: 8.68E-08 mmHg at 25°C; (12)EINECS: 210-498-3; (13)Melting point: 106-108 °C; (14)alpha: -35.1 oC (c=2,H2O); (15)Storage temp: 2-8°C; (16)Solubility: H2O: 100 mg/mL with heating.

3. Structure Descriptors of N-Acetyl-cysteine

You could convert the following datas into the molecular structure:
(1)InChI: InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1
(2)InChIKey: InChIKey=PWKSKIMOESPYIA-BYPYZUCNSA-N
(3)Smiles: [C@@H](NC(=O)C)(C(=O)O)CS

4. Toxicity of N-Acetyl-cysteine

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	multiple routes	8480mg/kg/3D- (8480mg/kg)	LIVER: LIVER FUNCTION TESTS IMPAIRED	Pediatrics. Vol. 79, Pg. 281, 1987.
dog	LD50	intraperitoneal	700mg/kg (700mg/kg)		Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 479, 1979.
dog	LD50	intravenous	700mg/kg (700mg/kg)		Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 479, 1979.
dog	LD50	oral	> 1gm/kg (1000mg/kg)		Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 479, 1979.
mouse	LD50	intraperitoneal	400mg/kg (400mg/kg)		National Technical Information Service. Vol. AD691-490,
mouse	LD50	intravenous	3800mg/kg (3800mg/kg)	BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Journal of Medicinal Chemistry. Vol. 10, Pg. 1172, 1967.
mouse	LD50	oral	4400mg/kg (4400mg/kg)		European Patent Application. Vol. #0192191,
rat	LD50	intravenous	1140mg/kg (1140mg/kg)	GASTROINTESTINAL: OTHER CHANGES	European Journal of Respiratory Diseases. Vol. 61(Suppl,
rat	LD50	oral	5050mg/kg (5050mg/kg)		Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

5. Safety Information of N-Acetyl-cysteine

Poison by intraperitoneal route. Moderately toxic by other routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO_x and SO_x.
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 22-24/25
22: Do not breathe dust
24/25: Avoid contact with skin and eyes
F 10-23: Keep under argon. Sensitive to air
WGK Germany: 3

6. Use of N-Acetyl-cysteine (CAS NO.616-91-1)

N-Acetyl-cysteine is a pharmaceutical drug used mainly as a mucolytic agent and in the management of paracetamol (acetaminophen) overdose. It is also used post-operatively, as a diagnostic aid, and in tracheotomy care. Oral N-Acetyl-cysteine is used for the prevention of radiocontrast-induced nephropathy. Besides can be used in Petroff's method i.e. liquefaction and decontamination of sputum, in preparation for diagnosis of tuberculosis.

Product Name

N-Acetyl-L-cysteine

Synthetic route

N-Acetyl-cysteine Consensus Reports

N-Acetyl-cysteine Specification

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