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73677

Sigma-Aldrich

4-Nitrophenyl β-D-glucuronide

β-glucuronidase substrate, chromogenic, ≥99.0% (TLC), powder or crystals, suitable as substrate for β-glucuronidase test

Synonym(s):

4-Nitrophenyl-β-D-glucopyranosiduronic acid, PNPG

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About This Item

Empirical Formula (Hill Notation):
C12H13NO9
CAS Number:
10344-94-2
Molecular Weight:
315.23
Beilstein/REAXYS Number:
1438576
EC Number:
233-753-0
MDL number:
MFCD00036210
UNSPSC Code:
12352204
PubChem Substance ID:
57652486
NACRES:
NA.32

product name

4-Nitrophenyl β-D-glucuronide, ≥99.0% (TLC)

assay

≥99.0% (TLC)

form

powder or crystals

optical activity

[α]20/D −102±3°, c = 1% in ethanol

impurities

≤0.05% free 4-nitrophenol
≤7% water

solubility

H2O: 0.1 g/mL, clear, faintly yellow

suitability

suitable as substrate for β-glucuronidase test

storage temp.

−20°C

SMILES string

O[C@@H]1[C@@H](O)[C@@H](O[C@@H]([C@H]1O)C(O)=O)Oc2ccc(cc2)[N+]([O-])=O

InChI

1S/C12H13NO9/c14-7-8(15)10(11(17)18)22-12(9(7)16)21-6-3-1-5(2-4-6)13(19)20/h1-4,7-10,12,14-16H,(H,17,18)/t7-,8-,9+,10-,12+/m0/s1

InChI key

QSUILVWOWLUOEU-GOVZDWNOSA-N

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Application

4-Nitrophenyl β-D-glucuronide has been used for determining the β-glucuronidase activity in urine samples, β-glucuronidase activity of bacteria in caecum content digesta and bovine liver. It has also been used to study the inhibitory effect of Phyllanthus amarus extracts on β-glucuronidase.

Substrates

Chromogenic substrate for β-glucuronidase (GUS) gene detection.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of Glycaro-1, 5-lactams and Tetrahydrotetrazolopyridine-5-carboxylates: Inhibitors of beta-D-Glucuronidase and alpha-L-Iduronidase
Pabba J, et al.
Helvetica Chimica Acta, 89(4), 635-666 (2006)
Effect of tobacco smoking on albumin concentration and beta-glucuronidase activity in urine of smelters
Bizonn A, et al.
Przegla?d Lekarski, 71(11), 581-584 (2014)
E E Guibert et al.
Experientia, 39(5), 527-528 (1983-05-15)
The effect of spironolactone (SP) on p-nitrophenol (PNP) glucuronidation was studied in isolated rat hepatocytes with appropriate viability conditions. A significant increase of protein concentration and PNP glucuronidation was found in the hepatocytes from SP-treated rats. Increased enzyme activity apparently
C Y Ng et al.
The Journal of pharmacology and experimental therapeutics, 295(2), 830-835 (2000-10-25)
Congestive heart failure has been shown to affect oxidative drug metabolism, however, there has been little study of its effects on drug conjugation. Using the isolated perfused livers from rats with right ventricular failure (RVF) due to pulmonary artery constriction
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