52-89-1

Basic information

• Product Name: L-Cysteine hydrochloride anhydrous
• Synonyms: L-(+)-α-amino-β-thiopropionic acid;L-β-mercapto;(2R)-2-Amino-3-sulfanylpropanoic acid hydrochloride;(2R)-2-Amino-3-mercaptopropanoic acid·hydrochloric acid;L-Cisteine·hydrochloride;L-Cysteine·hydrochloric acid;L-Cysteine hydrochloride anhydrous, extra pure;L-Cysteine hydrochlo
• CAS NO: 52-89-1
• Molecular Formula: C₃H₈NO₂S*Cl
• Molecular Weight: 157.62
• EINECS: 200-157-7
• Product Categories: Amino Acid Derivatives;Amino acidsPeptide Synthesis;Cysteine/Cystine;Amino Acids and Vitamins;Amino AcidsNutrition Research;Reagents and Supplements;Food and Feed Additive;Cysteine [Cys, C];Amino Acids;Nutritional Supplements;L-Amino Acids;Amino acidsIon Channels;NMDA Agonists;Biochemicals Found in Plants;Excitatory Amino Acids;Ionotropic Glutamate Receptor ModulatorsNeurotransmitters;Ligand-Gated Ion Channels;Nutrition Research
• Mol File: 52-89-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 180°C
• Boiling Point: 293.9 ºC at 760 mmHg
• Flash Point: 131.5 ºC
• Appearance: White to light brown/Solid
• Vapor Pressure: 0.000183mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility: SOLUBLE
• Sensitive: Hygroscopic
• Stability: Stable, but light, moisture and air sensitive. Incompatible with strong oxidizing agents, some metals.
• Merck: 14,2781
• BRN: 3560277
• CAS DataBase Reference: L-Cysteine hydrochloride anhydrous(CAS DataBase Reference)
• NIST Chemistry Reference: L-Cysteine hydrochloride anhydrous(52-89-1)
• EPA Substance Registry System: L-Cysteine hydrochloride anhydrous(52-89-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: HA2275000
• F: 3-10-23
• TSCA: Yes
• Hazardous Substances Data: 52-89-1(Hazardous Substances Data)

Usage

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 52-89-1 differently. You can refer to the following data:
1. As dough conditioner.
2. L-Cysteine hydrochloride, anhydrous is widely used as additive in food production. It is used as an antioxidant to promote fermentation and keep the flavor. It is also used in cosmetics and animal feed.

Definition

ChEBI: A hydrochloride obtained by combining L-cysteine with one molar equivalent of hydrogen chloride.

General Description

L-cysteine is a sulfur-containing amino acid.

Biochem/physiol Actions

NMDA glutamatergic receptor agonist that is also an agonist at AMPA glutamatergic receptors at high concentrations.

Safety Profile

: Moderately toxic by intraperitoneal, intravenous, and possibly other routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, SOx, and Cl-.

Purification Methods

Likely impurities are cystine and tyrosine. Crystallise the salt from MeOH by adding diethyl ether, or from hot 20% HCl. Dry it under vacuum over P2O5. Hygroscopic. [Beilstein 4 III 1580, 1600.]

InChI:InChI=1/C3H7NO2S.ClH/c4-2(1-7)3(5)6;/h2,7H,1,4H2,(H,5,6);1H/p-1

Synthetic route

(3R)-2-methyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester (2519-89-3, 6436-58-4, 15263-39-5, 45789-42-2) → l-cysteine hydrochloride (52-89-1)

Conditions	Yield
With hydrogenchloride; water for 24h; Inert atmosphere; Reflux;	94%

N-(tert-butoxycarbonyl)-S-(N-methylcarbamoyl)cysteine methyl ester (120033-48-9) → l-cysteine hydrochloride (52-89-1) + S-(N-methylcarbamoyl)cysteine hydrochloride (120033-46-7)

Conditions	Yield
With hydrogenchloride for 168h;	A 15% B 83%

S-(diphenyl-4-pyridylmethyl)-L-cysteine (62982-12-1) → diphenyl(pyridin-4-yl)methanol (1620-30-0) + l-cysteine hydrochloride (52-89-1)

Conditions	Yield
With mercury(II) diacetate In water; acetic acid for 0.25h; Product distribution; other reagent (zinc dust, 80percent acetic acid, 15 min);

cycloforskamide (1447695-69-3) → C5H9NO2*ClH + l-cysteine hydrochloride (52-89-1) + L-valine hydrochloride (17498-50-9, 25616-14-2, 31320-20-4) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7) + D-alloisoleucine hydrochloride

Conditions	Yield
With hydrogenchloride; water at 110℃; for 24h;

l-cysteine hydrochloride (52-89-1) + benzaldehyde (100-52-7) → (4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid (196930-46-8)

Conditions	Yield
Stage #1: l-cysteine hydrochloride With sodium hydroxide In water Stage #2: benzaldehyde In ethanol; water at 20℃; for 3h;	100%
With potassium acetate In methanol; water at 0 - 25℃; for 6h;	98%
Stage #1: l-cysteine hydrochloride With potassium carbonate In water Stage #2: benzaldehyde In methanol; water at 25℃; for 3h;	98%

(9H-fluoren-9-yl)methyl 4-methylbenzenesulfonaye (71532-40-6) + l-cysteine hydrochloride (52-89-1) → (R)-9H-fluorenyl-9-methyl-L-cysteine (84888-38-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	100%

formaldehyd (50-00-0) + l-cysteine hydrochloride (52-89-1) → (R)-thiazolidine-4-carboxylic acid hydrochloride (67089-84-3)

Conditions	Yield
at 20℃; for 1h; Solid phase reaction; cyclocondensation;	100%
Stage #1: formaldehyd; l-cysteine hydrochloride With sodium hydroxide In water at 20℃; for 24h; Stage #2: With pyridine In ethanol; water at 0℃;	80%

l-cysteine hydrochloride (52-89-1) + benzonitrile (100-47-0) → (4R)-2-phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid (19983-15-4, 116179-34-1, 62096-93-9)

Conditions	Yield
With sodium hydrogencarbonate In methanol at 70℃; pH=7; aq. phosphate buffer; Inert atmosphere;	99%
With sodium hydrogencarbonate In methanol; aq. phosphate buffer for 72h; pH=6; Reflux;	73%
With piperidine; sodium hydrogencarbonate In ethanol

Methoxycarbonylsulfenyl chloride (26555-40-8) + l-cysteine hydrochloride (52-89-1) → S-(methoxycarbonylsulfenyl)cysteine hydrochloride

Conditions	Yield
With hydrogenchloride In methanol at 0℃; for 1h;	99%

salicylonitrile (611-20-1) + l-cysteine hydrochloride (52-89-1) → (R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid (115921-06-7)

Conditions	Yield
With sodium hydrogencarbonate In methanol; aq. phosphate buffer for 72h; pH=6; Reflux;	99%
Stage #1: salicylonitrile; l-cysteine hydrochloride With sodium hydrogencarbonate In ethanol for 0.5h; Heating; Stage #2: With piperidine In ethanol for 12h; pH=9; Heating; Stage #3: With hydrogenchloride In ethanol pH=1.5;	67%

benzyl (E)-3-((2-cyanobenzo[d]thiazol-6-yl)thio)acrylate + l-cysteine hydrochloride (52-89-1) → (S)-2-(6-mercaptobenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
With potassium carbonate In water; dimethyl sulfoxide at 20℃; for 0.166667h; Inert atmosphere;	99%

furfural (98-01-1) + l-cysteine hydrochloride (52-89-1) → (2RS,4R)-furan-2-yl-thiazolidine-4-carboxylic acid (72678-98-9)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 6h;	98%
With sodium acetate In ethanol; water at 25℃; for 3h;	87%
With ethanol; potassium acetate

triphenylmethyl alcohol (76-84-6) + l-cysteine hydrochloride (52-89-1) → S-trityl-L-cysteine (2799-07-7)

Conditions	Yield
Stage #1: triphenylmethyl alcohol; l-cysteine hydrochloride With trifluoroacetic acid for 2h; Stage #2: With sodium acetate; sodium hydroxide In diethyl ether; water at 0℃; pH=5 - 6;	98%
With trifluoroacetic acid for 3h; Inert atmosphere;	96%
With choline chloride; urea In trifluoroacetic acid at 25℃; for 2h;	95%

l-cysteine hydrochloride (52-89-1) + acetonitrile (75-05-8) → sodium 2-methyl-2-thiazolin-4-carboxylate

Conditions	Yield
With sodium ethanolate In ethanol for 11h; Heating;	98%

l-cysteine hydrochloride (52-89-1) + phenyl chloroformate (1885-14-9) → 2-oxothiazolidine-4(R)-carboxylic acid (19771-63-2)

Conditions	Yield
With sodium hydroxide In toluene at 40℃; for 2h;	98%
Stage #1: l-cysteine hydrochloride With sodium hydroxide In water at 0 - 9℃; Stage #2: phenyl chloroformate In water; toluene at 25℃; for 2h;	71%
With sodium hydroxide In water; toluene at 0 - 30℃; for 2h;
With hydrogenchloride; sodium hydroxide In water; toluene at 25℃; for 2h; pH=1;

l-cysteine hydrochloride (52-89-1) + 3-(3-tert-butoxycarbonylamino)benzonitrile (145878-50-8) → C15H18N2O4S (1401249-37-3)

Conditions	Yield
With sodium hydrogencarbonate In methanol; aq. phosphate buffer for 72h; pH=6; Reflux;	98%

pentafluorobenzenesulfenyl chloride (27918-31-6) + l-cysteine hydrochloride (52-89-1) → ((pentafluorophenyl)disulfanyl)cysteine

Conditions	Yield
In acetic acid at 70℃; for 3.5h;	98%

pentafluorobenzenesulfenyl chloride (27918-31-6) + l-cysteine hydrochloride (52-89-1) → S-(pentafluorophenylsulfanyl)-L-cysteine

Conditions	Yield
With acetic acid In acetic acid at 70℃; for 3.5h;	98%

l-cysteine hydrochloride (52-89-1) + 7β-chloroacetamido-7α-methoxy-3-(1-methyl-1H-tetrazole-5-mercaptomethyl)-3-cephem-4-carboxylic acid (57617-09-1) → (6R,7S)-7-[(S)-2-(2-amino-2-carboxyethylmercapto)acetamido]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (75498-96-3)

Conditions	Yield
With ethylenediaminetetraacetic acid; sodium thiosulfate In water at 50℃; Concentration; Temperature;	97.9%

C85H141N7O43S + l-cysteine hydrochloride (52-89-1) → C82H142N8O45S

Conditions	Yield
With tris-(2-carboxyethyl)-phosphine hydrochloride In water at 20℃; for 3h; pH=Ca. 7;	97%

l-cysteine hydrochloride (52-89-1) + 4-cyanobenzaldehyde (105-07-7) → (2RS,4R)-2-(4-cyano-phenyl)-thiazolidine-4-carboxylic acid (280108-15-8)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 6h;	96%
With sodium hydroxide In ethanol; water	63%
With potassium acetate In methanol; water at 20℃;

l-cysteine hydrochloride (52-89-1) + 2-nitro-benzaldehyde (552-89-6) → (2RS,4R)-2-(2-nitro-phenyl)-thiazolidine-4-carboxylic acid (72693-56-2, 112928-36-6, 112928-37-7)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 6h;	96%
With sodium hydrogencarbonate In water; dimethyl sulfoxide at 20℃;	91%

(2S)-2-[(tert-butyloxycarbonyl)amino]thiopropionic acid S-phenyl ester (92645-20-0) + l-cysteine hydrochloride (52-89-1) → N-(tert-butoxycarbonyl)-L-alanyl-L-cysteine (86810-06-2)

Conditions	Yield
Stage #1: l-cysteine hydrochloride With sodium tetrahydroborate In methanol at 20℃; for 1h; Inert atmosphere; Stage #2: (2S)-2-[(tert-butyloxycarbonyl)amino]thiopropionic acid S-phenyl ester In methanol at 20℃; Inert atmosphere;	96%
Stage #1: l-cysteine hydrochloride With sodium tetrahydroborate In methanol for 1h; Inert atmosphere; Stage #2: (2S)-2-[(tert-butyloxycarbonyl)amino]thiopropionic acid S-phenyl ester In methanol

l-cysteine hydrochloride (52-89-1) + 2-nitrophenylmethyl bromide (3958-60-9) → S-(2-nitrobenzyl)-L-cysteine

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 1h; Inert atmosphere;	96%

l-cysteine hydrochloride (52-89-1) + chloroacetic acid (79-11-8) → carbocisteine (638-23-3)

Conditions	Yield
With ammonia; ammonium bicarbonate In water at 20 - 50℃; for 0.5h; pH=7.5; Reagent/catalyst; Temperature; pH-value; Large scale;	96%

2-cyano-6-aminobenzothiazole (7724-12-1) + l-cysteine hydrochloride (52-89-1) → potassium (S)-2-(6-aminobenzo[d]thiazol-2-yl) -4,5-dihydrothiazole-4-carboxylate

Conditions	Yield
Stage #1: 2-cyano-6-aminobenzothiazole; l-cysteine hydrochloride In methanol; water at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With potassium carbonate In methanol; water for 0.666667h; Inert atmosphere;	96%

l-cysteine hydrochloride (52-89-1) + salicylaldehyde (90-02-8) → (2RS,4R)-2-(2-hydroxy-phenyl)-thiazolidine-4-carboxylic acid (201942-90-7)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 6h;	95%
With sodium hydrogencarbonate In water; dimethyl sulfoxide at 20℃;	78%
With ethanol; alkali cetate
With ethanol; alkali cetate
With sodium acetate In ethanol; water at 20℃; for 24h;

3-phenylpropyl isothiocyanate (2627-27-2) + l-cysteine hydrochloride (52-89-1) → S--L-cysteine (137915-13-0)

Conditions	Yield
With sodium hydroxide In ethanol; water for 48h; Ambient temperature;	95%

l-cysteine hydrochloride (52-89-1) + hematoporphyrin IX dihydrochloride (17696-69-4) → porphyrin c

Conditions	Yield
With L-valine; acetic acid for 0.666667h; Ambient temperature;	95%
With hydrogen bromide glacial acetic acid, 21 deg C, 40 min; heating 45 min, 0.01 mm Hg;	95%

l-cysteine hydrochloride (52-89-1) + acetone (67-64-1) → 2,2-dimethyl-thiazolidine-4(R)-carboxylic acid (58166-38-4)

Conditions	Yield
for 3.5h; Reflux;	95%
for 1.5h; Heating / reflux;	92%
for 6h; Reflux;	88%

(4-methylphenyl)diphenylmethanol (5440-76-6) + l-cysteine hydrochloride (52-89-1) → NSC123139 (61137-68-6)

Conditions	Yield
With choline chloride; urea In trifluoroacetic acid at 25℃; for 2h;	95%
(i) BF3-Et2O, AcOH, (ii) aq. NaOAc; Multistep reaction;

p-methoxytrityl alcohol (847-83-6) + l-cysteine hydrochloride (52-89-1) → NSC123528 (177582-20-6)

Conditions	Yield
With choline chloride; urea In trifluoroacetic acid at 25℃; for 2h;	95%
(i) BF3-Et2O, AcOH, (ii) aq. NaOAc; Multistep reaction;

m-cyanophenol (873-62-1) + l-cysteine hydrochloride (52-89-1) → (R)-2-(3'-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid sodium salt

Conditions	Yield
Stage #1: m-cyanophenol; l-cysteine hydrochloride With sodium hydrogencarbonate In ethanol for 1h; Heating; Stage #2: With piperidine In ethanol for 48h; pH=9; Heating;	95%

l-cysteine hydrochloride (52-89-1) + 2'-(2-hydroxyphenyl)-2'-thiazole-4'-carboxaldehyde (83053-39-8) → 2'-(2-hydroxyphenyl)-2'',3'',4'',5''-tetrahydro[2'',4']bisthiazolyl-4''-carboxylic acid

Conditions	Yield
With potassium acetate In ethanol; water at 20℃; for 1h;	95%

Upstream product

• 2519-89-3 (4R)-2-methyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester 
• 1447695-69-3 cycloforskamide 
• 62982-12-1 S-(diphenyl-4-pyridylmethyl)-L-cysteine 
• 120033-48-9 N-(tert-butoxycarbonyl)-S-(N-methylcarbamoyl)cysteine methyl ester 

Downstream Products

• 2799-07-7 S-trityl-L-cysteine 
• 102873-69-8 N-[(Ξ)-benzoylamino-((2Ξ,4R)-4-carboxy-thiazolidin-2-yl)-acetyl]-L-cysteine 
• 14510-12-4 S-(2-phenylethyl)-L-cysteine 
• 91919-78-7 cysteinyldimethylthioarsenite 
• 100370-20-5 (L)-S-(3-phenylpropyl)cysteine 
• 5410-61-7 S_.S'-(3-amino-4-hydroxy-phenylarsanediyl)-bis-L-cysteine 
• 50739-30-5 (2RS,4R)-2-benzylthiazolidine-4-carboxylic acid 
• 72678-97-8 (4R)-2-(1-naphtyl)-1,3-thiazolidine-4-carboxylic acid 
• 201942-90-7 (2RS,4R)-2-(2-hydroxy-phenyl)-thiazolidine-4-carboxylic acid 
• 2936-69-8 S-(2-aminoethyl)-L-cysteine 
• 5443-40-3 S-isopropyl-L-cysteine 
• 42258-90-2 (R)-thiazolidine-4-carboxylic acid methyl ester 
• 336193-86-3 methyl (4R)-2-methylthiazolidine-4-carboxylate 
• 58166-38-4 2,2-dimethyl-thiazolidine-4(R)-carboxylic acid 

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