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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:
Molecular Weight:
315.23
Beilstein:
1438576
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
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 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

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)
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)
M F Massenti et al.
Bollettino dell'Istituto sieroterapico milanese, 60(1), 26-30 (1981-01-01)
Beta-glucuronidase activity has been investigated in 1,221 Enterobacteriaceae strains. The test, using p-nitrophenyl-beta-D-glucuronide (pNPGlcU) agar culture, can be included easily in the routine Enterobacteriaceae biochemical assays. The test is discriminating for Enterobacteriaceae genera and species and useful for identification of
Rapid separation of p-nitrophenol and its glucuronide and sulfate conjugates by reversed-phase high-performance liquid chromatography.
G Diamond et al.
Journal of chromatography, 177(2), 368-371 (1979-09-21)

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