Procysteine

Base Information

• Chemical Name: Procysteine
• CAS No.: 19771-63-2
• Deprecated CAS: 163675-62-5
• Molecular Formula: C4H5 N O3 S
• Molecular Weight: 147.155
• Hs Code.: 2934999090
• European Community (EC) Number: 606-375-2
• UNII: X7063P804E
• DSSTox Substance ID: DTXSID501318247
• Nikkaji Number: J47.648J
• Wikidata: Q27216284
• Metabolomics Workbench ID: 153251
• ChEMBL ID: CHEMBL442218
• Mol file: 19771-63-2.mol

Synonyms:2-oxo-4-thiazolidine carboxylic acid;2-oxothiazolidine-4-carboxylate;2-oxothiazolidine-4-carboxylic acid;2-oxothiazolidine-4-carboxylic acid, (R)-isomer;2-oxothiazolidine-4-carboxylic acid, (S)-isomer;L-2-OTZD-4-CXA;L-2-oxothiazolidine-4-carboxylate;oxothiazolidinecarboxylic acid;Procysteine

Chemical Property of Procysteine

Chemical Property:

• Appearance/Colour: WHITE TO OFF-WHITE POWDER
• Melting Point: 174 °C (dec.)(lit.)
• Refractive Index: -64 ° (C=1, H2O)
• Boiling Point: °Cat760mmHg
• PKA: pKa (22°): 3.32
• Flash Point: °C
• PSA: 91.70000
• Density: 1.582 g/cm³
• LogP: 0.22480
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: Soluble in water
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 146.99901420
• Heavy Atom Count: 9
• Complexity: 158

Purity/Quality:

90%, ^*data from raw suppliers

Otc ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NC(=O)S1)C(=O)O
• Isomeric SMILES: C1[C@H](NC(=O)S1)C(=O)O
• Recent ClinicalTrials: A Double-Blind, Randomized Parallel Group Study Comparing Procysteine to Placebo in HIV-Infected Patients Who Are Taking Antiretroviral Nucleosides
• Uses: (R)-(-)-2-Oxothiazolidine-4-carboxylic Acid or Procysteine is a precursor to glutathione (GSH) which is an important antioxidant in plants, animals and fungi.

Technology Process of Procysteine

There total 6 articles about Procysteine 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: 98.0%

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

Guidance literature:

With sodium hydroxide; In toluene; at 40 ℃; for 2h;

DOI:10.1002/chem.200400733

Reference yield: 77.0%

L-Cysteine (52-90-4) + bis(trichloromethyl) carbonate (32315-10-9) → 2-oxothiazolidine-4(R)-carboxylic acid (19771-63-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; Ambient temperature;

DOI:10.1080/00397919308012605

Reference yield:

phosgene (75-44-5) + L-Cysteine (52-90-4) → 2-oxothiazolidine-4(R)-carboxylic acid (19771-63-2)

Guidance literature:

With potassium hydroxide; In toluene; at -5 ℃;

DOI:10.1246/bcsj.37.242

upstream raw materials:

phosgene

L-Cysteine

bis(trichloromethyl) carbonate

L-2-oxothiazolidine-4-carboxylic acid methyl ester

Downstream raw materials:

L-2-oxothiazolidine-4-carboxylic acid methyl ester

(R)-4-acetyl-2-oxothiazolidine

(R)-2-oxothiazolidine-4-carboxylic acid ethyl ester

tetrahydrothiazolo[3,4-a]pyrazine-3,5,8-trione

Refernces

• 1、 -. "Method for 2-oxothiazolidine-4-carboxylic acid for cellular glutathione". Page/Page column 9; 10. . Retrieved 2019/04/15.
• 2、 Seki, Masahiko,Hatsuda, Masanori,Mori, Yoshikazu,Yoshida, Shin-Ichi,Yamada, Shin-Ichi,Shimizu, Toshiaki. "A practical synthesis of (+)-biotin from L-cysteine". . p. 6102 - 6110. Retrieved 2007/10/03.