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Sigma-Aldrich

4-Nitrophenyl β-D-glucuronide

≥99.0% (TLC)

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Synonym(s):
4-Nitrophenyl-β-D-glucopyranosiduronic acid, PNPG
Empirical Formula (Hill Notation):
C12H13NO9
CAS Number:
10344-94-2
Molecular Weight:
315.23
Beilstein:
1438576
EC Number:
233-753-0
MDL number:
MFCD00036210
PubChem Substance ID:
57652486
NACRES:
NA.32

Quality Level

200

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 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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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)
H Iwabuchi et al.
Journal of chromatography, 414(1), 139-148 (1987-02-20)
Molecular-secondary-ion mass spectrometry (SIMS) is a suitable method for the analysis of nonvolatile substances such as conjugated metabolites of drugs. We have developed a simple method for the direct SIMS measurement of conjugates following thin-layer chromatography without any extraction procedure.
P P Wickramanayake et al.
Biomedical mass spectrometry, 12(3), 127-133 (1985-03-01)
Mass spectra of a series of chloro- and nitrophenylglucuronides by liquid secondary ion (LSI) mass spectrometry were obtained. In the positive ion mode class characteristic fragmentations and adduct ions are observed only in the presence of alkali salt additives. No
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
beta-Glucuronidase Inhibitory Effect of Phenolic Constituents from Phyllanthus amarus.
Joshi CS and Sanmuga Priya E
Pharmaceutical biology, 45(5), 363-365 (2007)
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