N-Acetylcysteine amide

Base Information

• Chemical Name: N-Acetylcysteine amide
• CAS No.: 38520-57-9
• Molecular Formula: C5H10 N2 O2 S
• Molecular Weight: 162.213
• Hs Code.: 2930909090
• European Community (EC) Number: 686-019-0
• UNII: 4N69717RKW
• DSSTox Substance ID: DTXSID30436398
• Nikkaji Number: J2.059.402K
• Wikipedia: Acetylcysteinamide
• Wikidata: Q15408428
• NCI Thesaurus Code: C87651
• Metabolomics Workbench ID: 154887
• Mol file: 38520-57-9.mol

Synonyms:2-acetamido-3-mercapto-L-propionamide;N-Acetylcysteinamide;N-Acetylcysteine amide

Chemical Property of N-Acetylcysteine amide

Chemical Property:

• Melting Point: 147-149 °C(Solv: ethanol (64-17-5))
• Boiling Point: 441.0±40.0 °C(Predicted)
• PKA: 9.21±0.10(Predicted)
• PSA: 115.47000
• Density: 1.226±0.06 g/cm3(Predicted)
• LogP: 0.89620
• Storage Temp.: 2-8°C
• Solubility.: H2O: ≥20mg/mL
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 162.04629874
• Heavy Atom Count: 10
• Complexity: 149

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Acetyl-L-cystine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC(CS)C(=O)N
• Isomeric SMILES: CC(=O)N[C@@H](CS)C(=O)N
• Uses: N-acetylcysteine amide has been used:to protect retinal pigment epithelium (RPE) from oxidative stressto show that increased expression of cell adhesion molecule 4 (CADM4) in oligodendrocytes inhibits myelinationto protect cells from apoptosis induced by shikonin plus erlotinib/gefitinibas a component in various culture media

Technology Process of N-Acetylcysteine amide

There total 2 articles about N-Acetylcysteine amide 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: 93.0%

Ac-Cys-OMe (7652-46-2) → (R)-2-acetylamino-3-mercapto-propionamide (38520-57-9)

Guidance literature:

With ammonium hydroxide; In water; at 20 ℃; for 168h;

Reference yield:

acetic anhydride (108-24-7) + L-cysteinamide (74401-72-2) → (R)-2-acetylamino-3-mercapto-propionamide (38520-57-9)

Guidance literature:

With sodium acetate; In tetrahydrofuran;

DOI:10.1021/jm00318a046

Reference yield: 93.0%

LYRANT-(3-mercaptopropionic acid)-Leu-NH2 + (R)-2-acetylamino-3-mercapto-propionamide (38520-57-9) → Ac-Cys(LYRANT)-NH2

Guidance literature:

With guanidine hydrochloride; In aq. phosphate buffer; at 20 ℃; for 2h; pH=7.8; Automated synthesizer;

DOI:10.1002/bip.22783

upstream raw materials:

acetic anhydride

L-cysteinamide

Ac-Cys-OMe

Downstream raw materials:

C₁₉H₂₈N₂O₁₁S₂

(2R,2R’)-3,3’-disulfanediyl bis(2 acetamidopropanamide)

Refernces

• 1、 -. "GOLD (I)-PHOSPHINE COMPOUNDS AS ANTI-BACTERIAL AGENTS". Page/Page column 35. . Retrieved 2015/12/17.
• 2、 -. "STABILIZED MULTI-FUNCTIONAL ANTIOXIDANT COMPOUNDS AND METHODS OF USE". Paragraph 00139; 00140. . Retrieved 2014/02/15.