Nitrocefin

Base Information

• Chemical Name: Nitrocefin
• CAS No.: 41906-86-9
• Molecular Formula: C21H16N4O8S2
• Molecular Weight: 516.512
• Hs Code.: 29349990
• European Community (EC) Number: 636-988-0
• UNII: EWP54G0J8F
• DSSTox Substance ID: DTXSID401318525
• Nikkaji Number: J17.395I
• Wikipedia: Nitrocefin
• Wikidata: Q1993962
• NCI Thesaurus Code: C76562
• Metabolomics Workbench ID: 152736
• ChEMBL ID: CHEMBL480517
• Mol file: 41906-86-9.mol

Synonyms:Cefinase;glaxo 87-312;nitrocefin;nitrocefin, (6R-trans)-isomer;nitrocefin, monosodium salt;nitrocefin, sodium salt, (6R-trans)-isomer

Chemical Property of Nitrocefin

Chemical Property:

• Appearance/Colour: Orange to Red Solid
• Vapor Pressure: 1.7E-32mmHg at 25°C
• Melting Point: 103-113° (dec); mp 167-169° (dec) (Lee)
• Refractive Index: 1.749
• Boiling Point: 872oC at 760 mmHg
• PKA: 2.50±0.50(Predicted)
• Flash Point: 481.2oC
• PSA: 231.89000
• Density: 1.67g/cm3
• LogP: 4.10510
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 516.04095583
• Heavy Atom Count: 35
• Complexity: 991

Purity/Quality:

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

Nitrocefin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CS3)C(=O)O)C=CC4=C(C=C(C=C4)[N+](=O)[O-])[N+](=O)[O-]
• Isomeric SMILES: C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CS3)C(=O)O)/C=C/C4=C(C=C(C=C4)[N+](=O)[O-])[N+](=O)[O-]
• Description: The generation of β-lactamases by bacteria affords resistance to several classes of β-lactam antibiotics, including penicillins and cephalosporins. Nitrocefin is a chromogenic cephalosporin substrate commonly used to detect β-lactamases in bacteria. The presence of β-lactamase activity is indicated by the appearance of a red color that is proportional in intensity to the original concentration of nitrocefin.
• Uses: Nitrocefin is a chromogenic β-lactamase substrate that undergoes colour change from yellow to red as the amide bond in the β-Lactam ring is hydrolyzed by β-lactamase. Nitrocefin undergoes colour chang es induced by lactamases produced by Gram-positive and Gram-negative bacteria. Several studies have utilized the colour changing properties of Nitrocefin for the detection of β-lactamase activity from bacterial cell extracts by isoelectric focusing and spectroscopy. Nitrocefin has also been used in studies involving β-lactamase resistant antibiotics.
• Biological Functions: In determination of b-lactamase activity in biological samples.Nitrocefin is a colorless or faint yellow cephalosporin antimicrobial that is hydrolyzed rapidly by most beta-lactamases.The hydrolysis product is pink.The bacterium to be tested is applied to a paper disk containing nitrocefin. A pink color developing within minutes (positive test) indicates a beta-lactamaseproducing bacterium.

Technology Process of Nitrocefin

There total 13 articles about Nitrocefin 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: 87.0%

C34H26N4O8S2 → Nitrocefin (41906-86-9)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.5h;

Reference yield:

2-thienylacetic acid chloride (39098-97-0) → Nitrocefin (41906-86-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 78 percent / potassium trimethylsilanolate / CH₂Cl₂; acetonitrile / 1 h / 20 °C

2.1: sodium iodide / butan-2-one / 20 °C

3.1: potassium trimethylsilanolate / CH₂Cl₂; acetonitrile / 1 h / -10 °C

3.2: 0.90 g / CH₂Cl₂; acetonitrile / 5 h / -10 - 20 °C

4.1: trifluoroacetic acid; anisole / CH₂Cl₂ / 0.25 h / cooling

With potassium trimethylsilonate; methoxybenzene; trifluoroacetic acid; sodium iodide; In dichloromethane; acetonitrile; butanone; 2.1: Finkelstein reaction / 3.2: Wittig reaction;

DOI:10.1021/jo0487395

Reference yield:

(6R,7R)-4-methoxybenzyl-3-(chloromethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (101182-25-6) → Nitrocefin (41906-86-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium iodide / butan-2-one / 20 °C

2.1: potassium trimethylsilanolate / CH₂Cl₂; acetonitrile / 1 h / -10 °C

2.2: 0.90 g / CH₂Cl₂; acetonitrile / 5 h / -10 - 20 °C

3.1: trifluoroacetic acid; anisole / CH₂Cl₂ / 0.25 h / cooling

With potassium trimethylsilonate; methoxybenzene; trifluoroacetic acid; sodium iodide; In dichloromethane; acetonitrile; butanone; 1.1: Finkelstein reaction / 2.2: Wittig reaction;

DOI:10.1021/jo0487395

upstream raw materials:

2-thienylacetic acid chloride

p-methoxybenzyl (6R,7R)-3-(2,4-dinitrostyryl)-7-(2-thienylacetamido)-3-cephem-4-carboxylate

(6R,7R)-4-methoxybenzyl-3-(chloromethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

7-Aminocephalosporanic acid

Refernces

• 1、 Lee, Mijoon,Hesek, Dusan,Mobashery, Shahriar. "A practical synthesis of nitrocefin". . p. 367 - 369. Retrieved 2007/10/03.