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L-Cysteine
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Name

L-Cysteine

 EINECS 200-158-2
CAS No. 52-90-4 Density 1.334 g/cm3
PSA 102.12000 LogP 0.02840
Solubility 280 g/L (25°C) in water Melting Point 220 °C
Formula C3H7NO2S Boiling Point 293.9 °C at 760 mmHg
Molecular Weight 121.16 Flash Point 131.5°C
Transport Information N/A Appearance white crystalline powder
Safety 36/37/39-26 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 52-90-4 (L-Cysteine) Hazard Symbols IrritantXi,HarmfulXn
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;

Article Data 359

L-Cysteine 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%

L-Cysteine Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

L-Cysteine 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

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