N-Acetyl-D-cysteine

Base Information

• Chemical Name: N-Acetyl-D-cysteine
• CAS No.: 26117-28-2
• Molecular Formula: C5H9 N O3 S
• Molecular Weight: 163.197
• Hs Code.: 2930909090
• European Community (EC) Number: 247-470-5
• NSC Number: 755856
• UNII: L305827QJJ
• DSSTox Substance ID: DTXSID60180751
• Nikkaji Number: J221.597G
• Wikidata: Q27896281
• Metabolomics Workbench ID: 140547
• ChEMBL ID: CHEMBL507900
• Mol file: 26117-28-2.mol

Synonyms:N-Acetyl-D-cysteine;26117-28-2;D-Cysteine, N-acetyl-;(2S)-2-acetamido-3-sulfanylpropanoic acid;(S)-2-Acetamido-3-mercaptopropanoic acid;L305827QJJ;EINECS 247-470-5;N-acetyl-d-cys;n-acetyl-d-cystein;Spectrum_000024;(S)-N-acetyl-cysteine;Lopac-A-7250;KBioSS_000384;DivK1c_000530;UNII-L305827QJJ;CHEMBL507900;SCHEMBL1384791;HMS501K12;KBio1_000530;KBio2_000384;KBio2_002952;KBio2_005520;DTXSID60180751;NINDS_000530;Pharmakon1600-01500105;BBA11728;MFCD00269768;NSC755856;AKOS006275410;NSC-755856;IDI1_000530;NCGC00015086-01;NCGC00015086-02;NCGC00094578-01;NCGC00094578-02;AS-17941;HY-136386;CS-0128949;D94631;EN300-6991250;Q27896281

Chemical Property of N-Acetyl-D-cysteine

Chemical Property:

• Vapor Pressure: 8.68E-08mmHg at 25°C
• Melting Point: 104-107°C
• Boiling Point: 407.7°C at 760 mmHg
• PKA: 3.25±0.10(Predicted)
• Flash Point: 200.4°C
• PSA: 108.69000
• Density: 1.294g/cm³
• LogP: 0.34580
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 163.03031432
• Heavy Atom Count: 10
• Complexity: 148

Purity/Quality:

99% ^*data from raw suppliers

N-Acetyl-D-cysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CS)C(=O)O
• Isomeric SMILES: CC(=O)N[C@H](CS)C(=O)O
• Uses: N-Acetyl-D-cysteine is an isomer of N-Acetyl Cysteine which can act as a radioprotectant against many aspects of oxidative damage due to high dose irradiation.

Technology Process of N-Acetyl-D-cysteine

There total 12 articles about N-Acetyl-D-cysteine 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:

2-Acetylamino-3-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-propionic acid → N-Acetylcysteine (7218-04-4,26117-28-2,616-91-1,7696-05-1)

Guidance literature:

With lithium perchlorate; In methanol; (electrolysis);

DOI:10.1021/ja00769a087

Reference yield:

N-acetyl-S-benzyl-D,L-cysteine (19538-71-7) → N-Acetylcysteine (7218-04-4,26117-28-2,616-91-1,7696-05-1)

Guidance literature:

With ammonia; sodium;

DOI:10.1021/jm00309a057

Reference yield:

ethyl N-acetyl-S-benzyl-D,L-cysteinate (118456-64-7) → N-Acetylcysteine (7218-04-4,26117-28-2,616-91-1,7696-05-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1 N aq. sodium hydroxide / 0.03 h / 65 °C

2: sodium / liquid ammonia / 0.75 h

With sodium hydroxide; sodium; In ammonia;

DOI:10.1021/jo00266a018

upstream raw materials:

N-acetyl-S-benzyl-D,L-cysteine

2-hydroxyethanethiol

ethyl N-acetyl-S-benzyl-D,L-cysteinate

N-Acetylcysteine

Downstream raw materials:

2-acetylamino-3-mercapto-propionic acid methyl ester

L-Cysteine

(S)-N-acetylcysteine

4-acetaminophenol

Refernces

• 1、 -. "Separation and purification method for acetylcysteine enantiomer". Paragraph 0062-0128. . Retrieved 2020/01/12.
• 2、 -. "COMPOSITIONS AND METHODS FOR THE TREATMENT OF COUGH". Paragraph 0095; 0096. . Retrieved 2013/12/03.