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Key Documents

N8883

Sigma-Aldrich

6-Nitro-3-(phenylacetamido)benzoic acid

≥98%

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About This Item

Empirical Formula (Hill Notation):
C15H12N2O5
CAS Number:
Molecular Weight:
300.27
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

Quality Level

Assay

≥98%

form

powder

solubility

ethanol: 9.80-10.20 mg/mL, clear, faintly yellow to yellow

storage temp.

2-8°C

SMILES string

OC(=O)c1cc(NC(=O)Cc2ccccc2)ccc1[N+]([O-])=O

InChI

1S/C15H12N2O5/c18-14(8-10-4-2-1-3-5-10)16-11-6-7-13(17(21)22)12(9-11)15(19)20/h1-7,9H,8H2,(H,16,18)(H,19,20)

InChI key

QHVQEQRGDKOHHC-UHFFFAOYSA-N

General description

6-Nitro-3-(phenylacetamido)benzoic acid is a chromogenic analog of penicillin.

Substrates

Substrate for penicillin amidase.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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I Miesiac et al.
Journal of chemical technology and biotechnology (Oxford, Oxfordshire : 1986), 55(1), 1-8 (1992-01-01)
The effects of various commercial and model surfactants of different structure and hydrophilicity were studied on water-in-oil (w/o) emulsion stability, potassium cation leakage and permeation of 6-nitro-3-phenylacetamide benzoic acid in a model system using Penicillin acylase (EC 3.5.1.11) immobilized in
Wynand B L Alkema et al.
European journal of biochemistry, 269(8), 2093-2100 (2002-05-03)
Penicillin acylase of Escherichia coli catalyses the hydrolysis and synthesis of beta-lactam antibiotics. To study the role of hydrophobic residues in these reactions, we have mutated three active-site phenylalanines. Mutation of alphaF146, betaF24 and betaF57 to Tyr, Trp, Ala or
W B Alkema et al.
Analytical biochemistry, 275(1), 47-53 (1999-11-05)
Determination of kinetic parameters of penicillin acylases for phenylacetylated compounds is complicated due to the low K(m) values for these substrates, the lack of a spectroscopic signal, and the strong product inhibition by phenylacetic acid. To overcome these difficulties, a
Q J Zhang et al.
Analytical biochemistry, 156(2), 413-416 (1986-08-01)
A simple, rapid assay for screening penicillin G acylase-producing bacteria is presented. The method is based on the formation of yellow 2-nitro-5-aminobenzoic acid by penicillin G acylase acting on 2-nitro-5-phenylacetaminobenzoic acid (NIPAB). NIPAB test paper is briefly applied to bacterial
Direct spectrophotometric measurement of enzyme activity in heterogeneous systems with insoluble substrate or immobilized enzyme.
B Galunsky et al.
Analytical biochemistry, 221(1), 213-214 (1994-08-15)

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