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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)
J A Perez-Pons et al.
European journal of biochemistry, 223(2), 557-565 (1994-07-15)
A beta-glucosidase gene (bgl3) from Streptomyces sp. QM-B814 (American Type Culture Collection 11238) has been cloned by functional complementation of a beta-glucosidase-negative mutant of Streptomyces lividans. An open-reading frame of 1440 nucleotides encoding a polypeptide of 479 amino acids was
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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