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52-90-4

Basic Information
CAS No.: 52-90-4
Name: L-Cysteine
Molecular Structure:
Molecular Structure of 52-90-4 (L-Cysteine)
Formula: C3H7NO2S
Molecular Weight: 121.17
Synonyms: L-Cysteine Free Base;2-Amino-3-mercapto-, (R)-;L-Cysteine (JAN);L-Cysteine Base/Hcl (mono/anhyd);(2R)-2-amino-3-mercaptopropanoic acid;Valine,3-mercapto-;alpha-Amino-beta-mercaptopropionic acid, L-;alpha-Amino-beta-thiolpropionic acid, L-;L-2-Amino-3-mercaptopropanoic acid;(2R)-2-amino-3-sulfanyl-propanoic acid;Half-cystine;L-2-Amino-3-mercaptopropionic acid;L-Cysteine Base;(+)-2-Amino-3-mercaptopropionic acid;H-Cys-OH;
EINECS: 200-158-2
Density: 1.334 g/cm3
Melting Point: 220 °C
Boiling Point: 293.9 °C at 760 mmHg
Flash Point: 131.5°C
Solubility: 280 g/L (25°C) in water
Appearance: white crystalline powder
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 36/37/38-20/21/22
Safety: 36/37/39-26
Transport Information:
PSA: 102.12000
LogP: 0.02840
Synthetic route
2544-31-2

S-(4-methoxybenzyl)-L-cysteine

52-90-4

L-Cysteine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;100%
With trifluoroacetic acid In dichloromethane at 20℃; Rate constant;
61925-77-7

Boc-cysteine(4-Me-Bn)

52-90-4

L-Cysteine

Conditions
ConditionsYield
With phenylthiotrimethylsilane; pertrimethylsilylated Nafion; 3-methyl-phenol; trifluoroacetic acid for 3h;100%
With ethandithiol; methoxybenzene; thallium(III) trifluoroacetate 1.) trifluoroacetic acid, 0 deg c, 60 min; 2.) 40 deg C, 5 h, pH=7.5 adjusted with 5percent NH4OH;
78221-55-3

S-(2,4,6-trimethylbenzyl)-L-cysteine

52-90-4

L-Cysteine

Conditions
ConditionsYield
With hydrogen fluoride; methoxybenzene at 0℃; for 0.5h; Product distribution; various time, reagents and temperature;100%
123043-33-4

S-benzyloxymethylcysteine

52-90-4

L-Cysteine

Conditions
ConditionsYield
With silver trifluoromethanesulfonate; methoxybenzene In trifluoroacetic acid Product distribution; other reagents;100%
103022-01-1

Z(OMe)-Cys(Ad)-OH*DCHA

52-90-4

L-Cysteine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;100%
With ethandithiol; methoxybenzene; thallium(III) trifluoroacetate 1.) trifluoroacetic acid, 0 deg c, 60 min; 2.) 40 deg C, 5 h, pH=7.5 adjusted with 5percent NH4OH; Yield given. Multistep reaction;

(2S,4R)-2-methyl-1,3-thiazolidine-2,4-dicarboxylic acid

A

52-90-4

L-Cysteine

B

541-50-4

2-acetoacetic acid

Conditions
ConditionsYield
With water at 90℃; Column which a srtongly acidic cation exchanger in the H+ form;A n/a
B 99.6%
56-89-3

L-cystine

52-90-4

L-Cysteine

Conditions
ConditionsYield
With ethandithiol at 40℃; for 5h; pH=7.5 adjusted with 5 percent NH4OH;98.5%
With ammonia; sodium Reduction;90%
With hydrogenchloride; tin man verduennt die Loesung, befreit sie mit H2S vom Zinn, verdunstet zur Trockne, loest den Rueckstand in Alkohol und faellt vorsichtig mit Ammoniak;
56976-06-8

N-(Carbo-tert-butoxy)-S-tert-butyl-L-cysteine

52-90-4

L-Cysteine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; diphenyl sulfide In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;97.1%
With ethandithiol; methoxybenzene; thallium(III) trifluoroacetate 1.) trifluoroacetic acid, 0 deg c, 60 min; 2.) 40 deg C, 5 h, pH=7.5 adjusted with 5percent NH4OH; Yield given. Multistep reaction;
56-89-3

L-cystine

A

52-90-4

L-Cysteine

B

498-40-8

L-Cysteic acid

Conditions
ConditionsYield
With hydrogenchloride; sulfuric acid; hydrogen bromide In water at 45℃; electrolysis (graphite sheets, i = 0.5 A/cm2);A 94%
B n/a
With hydrogenchloride; sulfuric acid; hydrogen bromide In water at 45℃; Product distribution; Mechanism; paired electrosynthesis (graphite sheets, i = 0.5 A/cm2);A n/a
B 94%
With hydrogenchloride at 40℃; Electrolysis;
19746-37-3

N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine

52-90-4

L-Cysteine

Conditions
ConditionsYield
With silver tetrafluoroborate; methoxybenzene In trifluoroacetic acid at 4℃; for 1h;93%
52-89-1

l-cysteine hydrochloride

52-90-4

L-Cysteine

Conditions
ConditionsYield
In acetone for 1.5h; Heating / reflux;92%
With pyridine; ethanol durch Faellung;
With ethanol; ammonia durch Neutralisation;
With sodium hydrogencarbonate In water; dimethyl sulfoxide at 20℃;
Boc-Cys-Merrifield resin

Boc-Cys-Merrifield resin

52-90-4

L-Cysteine

Conditions
ConditionsYield
With dimethyl ether-poly(hydrogen fluoride) at 0℃; for 1h;91%
34592-47-7

L-thioproline

52-90-4

L-Cysteine

Conditions
ConditionsYield
With hydroxylamine hydrochloride83%
With hydroxylamine hydrochloride In methanol reflux, 120 min, ice bath, 60 min;82%
Conditions
ConditionsYield
With porcine kidney D-amino acid oxidase (EC 1.4.3.3.); sodium cyanoborohydride; flavin adenine dinucleotide In phosphate buffer at 37℃;77%
232617-16-2

2(R,S)-D-gluco-(1',2',3',4',5'-pentahydroxypentyl)-thiazolidine-4(R)-carboxylic acid

52-90-4

L-Cysteine

Conditions
ConditionsYield
With hydroxylamine hydrochloride In methanol; water for 2.5h; Heating;74%
57918-01-1, 124650-46-0

(2R,4R)-2-(D-galacto-1,2,3,4,5-Pentahydroxypentyl)-4-thiazolidincarbonsaeure

52-90-4

L-Cysteine

Conditions
ConditionsYield
With hydroxylamine hydrochloride In methanol for 3h; Heating;73%

56-89-3

L-cystine

Conditions
ConditionsYield
With 3-bromo-2-(1-hydroxycyclohexyl)[1,2]selenazolo[2,3-a]pyridinium chloride; dihydrogen peroxide In methanol; water at 20℃; for 0.166667h;100%
With dihydrogen peroxide; sodium iodide In water at 25℃; for 1h; Cooling with ice;100%
With bis(4-methoxyphenyl)telluride; rose bengal In water; isopropyl alcohol at 0℃; for 0.833333h; Irradiation;99%
52-90-4

L-Cysteine

106-93-4

ethylene dibromide

14344-49-1

S,S'-ethanediyl-bis-L-cysteine

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water at 70 - 90℃; for 1h;100%
With sodium hydrogencarbonate88%
67-56-1

methanol

52-90-4

L-Cysteine

18598-63-5

L-cysteine methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride In methanol for 3h; Reflux; Inert atmosphere;100%
With acetyl chloride at 0℃; for 2h; Reflux;96%
Stage #1: methanol With acetyl chloride at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: L-Cysteine at 20℃; for 36h; Inert atmosphere;
94%
52-90-4

L-Cysteine

73243-09-1

(R)-2-Amino-3-(4-methoxy-phenylmethanesulfinyl)-propionic acid

56-89-3

L-cystine

Conditions
ConditionsYield
With dimethylsulfide; trifluorormethanesulfonic acid In trifluoroacetic acid at 0℃; for 1h;100%
52-90-4

L-Cysteine

2043-61-0

cyclohexanecarbaldehyde

56888-62-1

(2RS,4R)-cyclohexylthiazolidine-4-carboxylic acid

Conditions
ConditionsYield
In ethanol at 20℃; for 5h;100%
52-90-4

L-Cysteine

tin(ll) chloride

bis(cysteinato-OS)tin(IV) dihydrochloride dihydrate

Conditions
ConditionsYield
With water In water aq. mixt. of educts allowed to evap. at room temp. over 3 d; dried in vac. at room temp.; elem. anal.;100%
52-90-4

L-Cysteine

251294-64-1

2-[N-(tert-butoxycarbonyl)aminomethyl]thiazole-4-carbonitrile

1132667-22-1

(R)-2-(2-tert-butoxycarbonylaminomethyl-thiazol-4-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions
ConditionsYield
With triethylamine In methanol Reflux;100%
Stage #1: L-Cysteine; 2-[N-(tert-butoxycarbonyl)aminomethyl]thiazole-4-carbonitrile With triethylamine In methanol Reflux;
Stage #2: With hydrogenchloride In water pH=~ 3 - 4;
100%
Stage #1: L-Cysteine; 2-[N-(tert-butoxycarbonyl)aminomethyl]thiazole-4-carbonitrile With water; sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
Stage #2: With formic acid; water In N,N-dimethyl-formamide Inert atmosphere;
97%
With triethylamine In methanol at 23℃; for 3h; Reflux;97%
With triethylamine In methanol for 3h; Reflux;97%
52-90-4

L-Cysteine

1240490-39-4

(2S,4R)-N-allyloxycarbonyl-2-cyano-4-methyl-azetidine

1240490-42-9

C12H16N2O4S

Conditions
ConditionsYield
In methanol at 70℃; for 15h; pH=7; aq. phosphate buffer; Inert atmosphere;100%
52-90-4

L-Cysteine

4-(5-phenyl-3-(selenocyanatomethyl)-1H-pyrazol-1-yl)benzenesulfonamide

4-(5-phenyl-3-(selenocyanatomethyl)-1H-pyrazol-1-yl)benzenesulfonamide

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

(4R)-2-sulfanylidene-1,3-thiazolidine-4-carboxylic acid

(4R)-2-sulfanylidene-1,3-thiazolidine-4-carboxylic acid

Conditions
ConditionsYield
With gold; cetyltrimethylammonim bromide; silver nitrate; ascorbic acid at 25℃;100%
52-90-4

L-Cysteine

C32H37N7O4S3

C35H41N7O6S4

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanol; aq. phosphate buffer at 70℃; for 4h; pH=5.95;100%
58-86-6

D-xylose

52-90-4

L-Cysteine

C8H14NO6S(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydroxide at 80℃; pH=9.5; Temperature; Flow reactor;100%
50-00-0

formaldehyd

52-90-4

L-Cysteine

100208-30-8

(R)-thiazolidine-4-carboxylic acid ; sodium-salt

Conditions
ConditionsYield
With sodium hydroxide at 80℃; pH=9.5; Temperature; Flow reactor;100%
52-90-4

L-Cysteine

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

N-formyl-S-((7bS,3R,4S,5aR,7aR)-7b-hydroxy-4-methyl-2-oxodecahydroindeno[1,7-bc]furan-3-yl)cysteine

Conditions
ConditionsYield
With triethylamine In d(4)-methanol for 24h;100%
With triethylamine In methanol at 20℃; for 30h;
52-90-4

L-Cysteine

251294-64-1

2-[N-(tert-butoxycarbonyl)aminomethyl]thiazole-4-carbonitrile

2-[2-[(tert-butoxycarbonyl)methyl]thiazol-4-yl]-4,5-dihydrothiazole-4-carboxylic acid

Conditions
ConditionsYield
With triethylamine In methanol Reflux;100%
52-90-4

L-Cysteine

2237-14-1

1,4-benzoquinone-d4

C9H8(2)H3NO4S

Conditions
ConditionsYield
In water at 20℃; for 1.16667h; Inert atmosphere;100%
52-90-4

L-Cysteine

C6H12N2O4S2*(x)ClH

Conditions
ConditionsYield
With hydrogenchloride; Cumene hydroperoxide; tert-butyl (S)-(tetrahydrotellurophen-3-yl)carbamate In dichloromethane; water at 25℃; Flow reactor;100%
52-90-4

L-Cysteine

26555-40-8

Methoxycarbonylsulfenyl chloride

3-[(methoxycarbonyl)dithio]-L-alanine

Conditions
ConditionsYield
In 1,4-dioxane at 0 - 20℃; Inert atmosphere;100%
52-90-4

L-Cysteine

nicotinic acid riboside 5'-monophosphate

bis((R)-1-carboxy-2-mercaptoethan-1-aminium)-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonatooxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

Conditions
ConditionsYield
In water pH=2 - 2.43; Inert atmosphere; Cooling with ice;100%
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    Product name: L-Cysteine CAS No.:52-90-4 Molecule Formula:C3H7NO2S Molecule Weight:121.15 Purity: 99.9% Package: 25kg/drum Description:White crystals or crystalline powder Manufacture Standards:AJI/USP Items

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    Specifications CAS No.: 52-90-4 MF: C3H7NO2S EINECS No.: 200-158-2 Place of Origin: Hubei, China (Mainland) Type: Vitamins, Amino Ac

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    L-Cysteine hydrochloride monohydrate Product Description Product Name:L-Cysteine Hydrochloride Monohydrate Other Name: L-cysteine hcl monohydrate; H-Cys-OH.HCl.H2O; H-Cys-OH.HCl.H_2O; L-Cysteine Hcl Mono; L-cysteine hydrochloride

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Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

1. Introduction of L-Cysteine

L-Cysteine, with the EINECS: 200-158-2, is one kind of white crystalline powder. For being sensitive to air, this chemical is stable but incompatible with oxidizing agents, bases. Water Solubility: 280 g/L (25 °C). Besides, it belongs to the Product Categories which include API intermediates;Cysteine [Cys, C];Amino Acids;Amino Acids and Derivatives;alpha-Amino Acids;Antioxidant;Biochemistry;Nutritional Supplements;L-Amino Acids;Amino Acids.

2. Properties of L-Cysteine

L-Cysteine has the following datas: (1)H bond acceptors: 3; (2)H bond donors: 3; (3)Freely Rotating Bonds: 4; (4)Polar Surface Area: 54.84 ?2; (5)Index of Refraction: 1.549; (6)Molar Refractivity: 28.9 cm3; (7)Molar Volume: 90.7 cm3; (8)Surface Tension: 58.9 dyne/cm; (9)Density: 1.334 g/cm3; (10)Flash Point: 131.5 °C; (11)Enthalpy of Vaporization: 58.69 kJ/mol; (12)Boiling Point: 293.9 °C at 760 mmHg; (13)Vapour Pressure: 0.000411 mmHg at 25°C; (14)Melting point: 220 °C (dec.)(lit.); (15)Alpha: 8.75 o (c=12, 2N HCl).

3. Structure Descriptors of L-Cysteine

You could convert the following datas into the molecular structure:
InChI: InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1 
InChIKey: InChIKey=XUJNEKJLAYXESH-REOHCLBHSA-N 
Smiles: C([C@H](CS)N)(O)=O

4. Safety Information of L-Cysteine
The Hazard Codes of L-Cysteine (CAS NO.52-90-4): Xn,Xi
The Risk Statements: 36/37/38-20/21/22
20/21/22: Harmful by inhalation, in contact with skin and if swallowed 
36/37/38: Irritating to eyes, respiratory system and skin 
The Safety Statements: 36/37/39-26
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice  
36/37/39: Wear suitable protective clothing, gloves and eye/face protection. WGK Germany: 3
RTECS: HA1600000
F: 10-23
HS Code: 29309012
Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx.
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4°C/39°F.) Store under nitrogen.

5. Use of L-Cysteine

L-Cysteine is a precursor in the food, pharmaceutical, and personal care industries. It is the mainly used for production of flavors. In the field of personal care, cysteine is used for permanent wave applications predominantly in Asia. Again the cysteine is used for breaking up the disulfide bonds in the hair's keratin. Besides, Cysteine is a very popular target for site-directed labeling experiments to investigate biomolecular structure and dynamics.

6. Production of L-Cysteine

Biosynthesis of  L-Cysteine (CAS NO.52-90-4):


7. Toxicity of L-Cysteine

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1400mg/kg (1400mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 1251, 1973.
mouse LD50 intravenous 1250mg/kg (1250mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 89, Pg. 1138, 1969.
 
mouse LD50 oral 660mg/kg (660mg/kg)   Archives of Toxicology. Vol. 41, Pg. 79, 1978.
 
mouse LD50 subcutaneous 1360mg/kg (1360mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA
Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 1251, 1973.
rat LD50 intraperitoneal 1620mg/kg (1620mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 1251, 1973.
rat LD50 intravenous 1140mg/kg (1140mg/kg)   Journal of the American College of Toxicology. Vol. 12, Pg. 113, 1993.
rat LD50 oral 1890mg/kg (1890mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Agents and Actions, A Swiss Journal of Pharmacology. Vol. 4, Pg. 125, 1974.
 
rat LD50 subcutaneous 1550mg/kg (1550mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 1251, 1973