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Merck
CN

73677

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
NACRES:
NA.32
PubChem Substance ID:
57652486
UNSPSC Code:
12352204
EC Number:
233-753-0
MDL number:
MFCD00036210
Beilstein/REAXYS Number:
1438576

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Product Name

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

InChI key

QSUILVWOWLUOEU-GOVZDWNOSA-N

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

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

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

Quality Level

200

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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.

General description

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7534
BCCL8087
BCCL2707
BCCH4350
BCCG4124

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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)
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 dietary honey on intestinal microflora and toxicity of mycotoxins in mice
El-Arab AME, et al.
BMC Complementary and Alternative Medicine, 6(1), 6-6 (2006)
J P Lehman et al.
Drug metabolism and disposition: the biological fate of chemicals, 9(1), 15-18 (1981-01-01)
Cytochrome P-450, NADPH-cytochrome P-450 reductase, and glucuronyltransferase were immobilized simultaneously on cyanogen bromide-activated Sepharose from phenobarbital-induced rabbit liver microsomes. The activity of the P-450 system was demonstrated by the N-demethylation of ethylmorphine and the O-demethylation of p-nitroanisole. p-Nitrophenol produced from
G F Rush et al.
The Journal of pharmacology and experimental therapeutics, 227(3), 658-662 (1983-12-01)
Female Fischer 344 rats administered p-nitrophenol (0.05 mmol/kg) excrete more p-nitrophenylglucuronide in the urine than males (35.9 +/- 2.9 vs. 14.1 +/- 4.0% of total urinary metabolites, respectively). In contrast, hepatic microsomes prepared from male rats have higher UDP-glucuronyltransferase activity
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