4-Nitrophenyl β-D-glucopyranoside

4-Nitrophenyl β-D-glucopyranoside is a chromogenic substrate for β-glucosidase. 4-Nitrophenyl β-D-glucopyranoside is converted to a colored product, p-nitrophenol that is easily detected spectrophotometrically at 405 nm when used in a β-glycosidase assay. 4-Nitrophenyl β-D-glucopyranoside is hydrolysed through intramolecular nucleophilic catalysis by the phosphate group in the 2-position. 4-Nitrophenyl β-D-glucopyranoside is promising for research of postmenopausal osteoporosis[1][2][3].

Product Specifications

CAS Number

[2492-87-7]

UNSPSC

12352200

Hazard Statement

H302, H372

Target

Biochemical Assay Reagents

Type

Biochemical Assay Reagents

Related Pathways

Others

Field of Research

Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/4-nitrophenyl-β-d-glucopyranoside.html

Purity

99.69

Solubility

DMSO : 125 mg/mL (ultrasonic; warming; heat to 60°C)

Smiles

O[C@H]1[C@@H](O[C@H](CO)[C@@H](O)[C@@H]1O)OC2=CC=C([N+]([O-])=O)C=C2

Molecular Formula

C12H15NO8

Molecular Weight

301.25

Precautions

H302, H372

References & Citations

[1]Alhifthi A, et al. Unimolecular, Bimolecular, and Intramolecular Hydrolysis Mechanisms of 4-Nitrophenyl β-d-Glucopyranoside. J Org Chem. 2021 Jul 16;86 (14) :9530-9539.|[2]Lee KH, et al. Ginkgonitroside, a new nitrophenyl glycoside and bioactive compounds from Ginkgo biloba leaves controlling adipocyte and osteoblast differentiation. Bioorg Med Chem Lett. 2021 Oct 15;50:128322. |[3]Rosie F D. Nucleophilic catalysis of glycoside hydrolysis. The hydrolysis of 4-nitrophenyl α-and β-D-glucopyranoside tetraphosphates[J]. Journal of the Chemical Society, Perkin Transactions 2, 1994 (10) : 2085-2090.