S-Nitroso-N-acetylpenicillamine

Base Information

• Chemical Name: S-Nitroso-N-acetylpenicillamine
• CAS No.: 79032-48-7
• Molecular Formula: C7H12N2O4S
• Molecular Weight: 220.249
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID80897531
• Nikkaji Number: J366.380I
• Wikipedia: S-Nitroso-N-acetylpenicillamine
• Wikidata: Q4048659
• ChEMBL ID: CHEMBL73188
• Mol file: 79032-48-7.mol

Synonyms:N-Acetyl-S-Nitrosopenicillamine;N2-Acetyl-S-Nitroso-D,L-Penicillinaminamide;S-Nitroso-N-Acetylpenicillamine;S-Nitrosylacetylpenicillamine;S-NONAP;SNAP (NO donor)

Chemical Property of S-Nitroso-N-acetylpenicillamine

Chemical Property:

• Appearance/Colour: green crystalline solid
• Melting Point: 150-151 ºC
• Refractive Index: 1.56
• PSA: 121.13000
• Density: 1.36 g/cm³
• LogP: 1.15980
• Storage Temp.: −20°C
• Solubility.: H2O: ≥2 mg/mL
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 220.05177804
• Heavy Atom Count: 14
• Complexity: 254

Purity/Quality:

98.5% ^*data from raw suppliers

S-Nitroso-N-acetyl-D-β,β-dimethylcysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(C(=O)O)C(C)(C)SN=O
• Isomeric SMILES: CC(=O)N[C@@H](C(=O)O)C(C)(C)SN=O
• Uses: The D-isomer of SNAP. Serves as an NO donor The D-isomer of SNAP. Serves as an NO donor.

Technology Process of S-Nitroso-N-acetylpenicillamine

There total 4 articles about S-Nitroso-N-acetylpenicillamine 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: 72.0%

N-acetyl-3,3-dimethyl-D-cysteine (15537-71-0) → S-nitroso-N-acetylpenicillamine (79032-48-7,81739-40-4)

Guidance literature:

With 3,3-dimethyl-2-nitroso-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide; trifluoroacetic acid; In acetonitrile; at 20 ℃; for 0.5h; Sealed tube;

DOI:10.1021/acs.orglett.1c00637

Reference yield:

N-acetyl-3,3-dimethyl-D-cysteine (15537-71-0) + S-nitroso-N-acetyl-DL-penicillamine (67776-06-1,81739-40-4) → NAP (59-53-0) + S-nitroso-N-acetylpenicillamine (79032-48-7,81739-40-4)

Guidance literature:

With phosphate buffer; ethylenediaminetetraacetic acid; for 0.0833333h; pH=7.4; Equilibrium constant;

DOI:10.1016/S0960-894X(00)00688-0

Reference yield:

NAP (59-53-0) → S-nitroso-N-acetylpenicillamine (79032-48-7,81739-40-4)

Guidance literature:

With hydrogenchloride; sulfuric acid; sodium nitrite;

upstream raw materials:

N-acetyl-3,3-dimethyl-D-cysteine

S-nitroso-N-acetyl-DL-penicillamine

NAP

S-nitroso-N-acetyl-penicillamine

Downstream raw materials:

N-acetyl-3,3-dimethyl-D-cysteine

S-nitroso-N-acetyl-DL-penicillamine

Refernces

• 1、 Galloway, Jordan D.,Sarabia, Cristian,Fettinger, James C.,Hratchian, Hrant P.,Baxter, Ryan D.. "Versatile new reagent for nitrosation under mild conditions". supporting information. p. 3253 - 3258. Retrieved 2021/05/06.
• 2、 -. "Nitric oxide-releasing packaging membranes". . . Retrieved 2019/12/25.