2-Ammonio-3-sulfanylpropanoate

Base Information

• Chemical Name: 2-Ammonio-3-sulfanylpropanoate
• CAS No.: 3374-22-9
• Molecular Formula: C₃H₇NO₂S
• Molecular Weight: 121.16
• Hs Code.: 29309013
• Mol file: 3374-22-9.mol

Synonyms:2-ammonio-3-sulfanylpropanoate;2-azaniumyl-3-sulfanylpropanoate;cysteine zwitterion;2-ammonio-3-mercaptopropanoate;CHEBI:35237;(+)H3N-CH(CH2SH)-COO(-);7242-49-1

Chemical Property of 2-Ammonio-3-sulfanylpropanoate

Chemical Property:

• Appearance/Colour: colorless or white crystaline powder
• Vapor Pressure: 0.000411mmHg at 25°C
• Melting Point: 225 °C (dec.)(lit.)
• Refractive Index: 1.549
• Boiling Point: 293.883 °C at 760 mmHg
• PKA: 2.07±0.10(Predicted)
• Flash Point: 131.536 °C
• PSA: 102.12000
• Density: 1.335 g/cm³
• LogP: 0.02840
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Aqueous Acid (Sparingly), DMSO (Sightly), Water (Slightly)
• Water Solubility.: Soluble in water (partly), 1 N HCl (25 mg/ml), ethanol, and acetic acid. Insoluble in acetone.
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 121.01974964
• Heavy Atom Count: 7
• Complexity: 69.8

Purity/Quality:

98%min ^*data from raw suppliers

DL-Cysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xn,Xi,C
• Statements: 20/21/22-36/37/38-22-35
• Safety Statements: 26-36-37/39-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(=O)[O-])[NH3+])S
• Uses: DL-Cysteine is a non-essential amino acid that can be synthesized by the human body under normal physiological conditions if a sufficient quantity of methionine is available. Cysteine is commonly used as a precursor in the food and pharmaceutical industries. Cysteine is used as a processing aid for baking, as an additive in cigarettes, as well as in the preparation of meat flavours. DL-Cysteine is a NMDA agonist at quisqualate receptors at high concentration.

Technology Process of 2-Ammonio-3-sulfanylpropanoate

There total 39 articles about 2-Ammonio-3-sulfanylpropanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.6%

R(-)-2-thioxothiazolidine-4-carboxylic acid (20933-67-9) → rac-cysteine (921-01-7,3374-22-9,4371-52-2,40143-64-4,40143-66-6,40143-69-9,52-90-4)

Guidance literature:

With hydrogenchloride; In water; at 60 ℃; for 3.5h;

Reference yield: 83.0%

2-amino-3-mercapto-propionic acid 9-bora-bicyclo[3.3.1]non-9-yl ester → rac-cysteine (921-01-7,3374-22-9,4371-52-2,40143-64-4,40143-66-6,40143-69-9,52-90-4)

Guidance literature:

With ethylenediamine; In tetrahydrofuran; for 0.0166667h; Heating;

DOI:10.1021/ol017241b

Reference yield: 40.0%

1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazole-2(3H)-thione + C10H11HgNO4S → rac-cysteine (921-01-7,3374-22-9,4371-52-2,40143-64-4,40143-66-6,40143-69-9,52-90-4) + bis(4-carboxyphenyl)mercury(II) + 1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one (2033-53-6)

Guidance literature:

1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazole-2(3H)-thione; C₁₀H₁₁HgNO₄S; In water; acetonitrile; at 37 ℃; for 1h;

With sodium hydrogencarbonate; In water; acetonitrile; at 37 ℃;

DOI:10.1002/chem.201605238

upstream raw materials:

cysteine disulfide

L-cystine

sodium cyanide

N,S-diacetyl-cysteine

Downstream raw materials:

(RS)-2-amino-3-<(2-chloroethyl)sulfanyl>propanoic acid hydrochloride

2-amino-3-(ethylthio)propionic acid

2-amino-3-(benzylthio)propionic acid

S-(4-chloro-benzyl)-cysteine

Refernces

COPPER-CATALYZED AUTOXIDATION OF CYSTEINE. THE AMOUNT OF HYDROGEN PEROXIDE PRODUCED UNDER VARIOUS CONDITIONS AND THE STOICHIOMETRY OF THE REACTION.

10.1246/bcsj.56.2065

The research investigates the copper-catalyzed autoxidation of cysteine and the production of hydrogen peroxide under various conditions. The study finds that the rate of autoxidation is dependent on the concentration of dissolved oxygen, with a double reciprocal plot indicating a possible Michaelis-Menten type mechanism for the reoxidation or oxygenation of Cu(I) species. The stoichiometric relation between cysteine consumed and hydrogen peroxide produced is confirmed to be 2:1 in dilute solutions. The presence of certain buffers, particularly phosphate, enhances the oxidation process. The formation and subsequent decomposition of hydrogen peroxide vary with pH, and the study suggests that the autoxidation process involves a two-equivalent oxidation-reduction mechanism.

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