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N8883

Sigma-Aldrich

6-Nitro-3-(phenylacetamido)benzoic acid

≥98%

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Empirical Formula (Hill Notation):
C15H12N2O5
CAS Number:
52033-70-2
Molecular Weight:
300.27
MDL number:
MFCD00043603
UNSPSC Code:
12352204
PubChem Substance ID:
24897865
NACRES:
NA.32

Quality Level

200

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
GHS05,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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
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
Preparation and general properties of crystalline penicillin acylase from Escherichia coli ATCC 11 105.
C Kutzbach et al.
Hoppe-Seyler's Zeitschrift fur physiologische Chemie, 355(1), 45-53 (1974-01-01)
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)
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
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