56193-44-3

Basic information

• Product Name: o-Nitrophenyl-α-D-glucopyranoside
• Synonyms: o-Nitrophenyl-alpha-D-glucopyranoside
• CAS NO: 56193-44-3
• Molecular Formula: C₁₂H₁₅NO₈
• Molecular Weight: 301.25
• EINECS: -0
• Mol File: 56193-44-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 186-188 °C
• Boiling Point: 572.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.599±0.06 g/cm3 (20 oC 760 Torr), Calc.*
• PKA: 12.69±0.70(Predicted)
• CAS DataBase Reference: o-Nitrophenyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: o-Nitrophenyl-α-D-glucopyranoside(56193-44-3)
• EPA Substance Registry System: o-Nitrophenyl-α-D-glucopyranoside(56193-44-3)

Safety Data

• Hazardous Substances Data: 56193-44-3(Hazardous Substances Data)

Usage

General Description

o-Nitrophenyl-α-D-glucopyranoside, also known as o-NPG, is a chemical compound used in biochemical and molecular biology research. It is a substrate for the enzyme β-glucosidase, and is commonly used as a chromogenic and fluorogenic substrate for the detection and quantification of this enzyme activity. When hydrolyzed by β-glucosidase, o-NPG releases a yellow-colored product, o-nitrophenol, which can be easily quantified spectrophotometrically at 405 nm. This makes o-NPG a valuable tool for studying enzyme kinetics, inhibitor screening, and high-throughput assays for β-glucosidase activity. Additionally, o-NPG has also been used as a model substrate for studying the degradation of cellulose and hemicellulose in plant cell walls, making it a versatile and widely used compound in biochemical and molecular biology research.

Upstream product

• 35023-96-2 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 3053-17-6 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 572-10-1 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride 
• 24624-80-4 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 88-75-5 2-hydroxynitrobenzene 
• 31208-93-2 o-nitrophenyl α-D-maltosid 
• 25878-60-8 D-galactose pentaacetate 

Downstream Products

• 144683-68-1 (2S,3R,4S,5R,6R)-2-[(3R,4R,5R,6S)-4,5-Dihydroxy-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 144683-67-0 (2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5R)-3,5-Dihydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 52340-78-0 (R,R)-hydroxybenzoin 
• 2325-10-2 (S,S)-hydrobenzoin 
• 144683-62-5 (2S,3R,4S,5R,6R)-2-((3R,4R,5R,6R)-4,5-Dihydroxy-6-phenethyloxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 144683-61-4 (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R)-3,5-Dihydroxy-2-phenethyloxy-tetrahydro-pyran-4-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 6801-91-8 n-decanyl β-D-galactopyranoside 
• 114102-86-2 o-nitrophenyl β-D-galactopyranoside 6-(diphenylphosphate) 
• 53144-51-7 (2'RS)-2',3'-epoxyprop-1'-yl-β-D-galactopyranoside 
• 88-75-5 2-hydroxynitrobenzene 
• 100-02-7 4-nitro-phenol 
• 139639-82-0 o-nitrophenyl β-D-galactopyranosyl<1->3>-β-D-galactopyranoside 
• 139639-81-9 o-nitrophenyl β-D-galactopyranosyl<1->6>-β-D-galactopyranoside 

Relevant articles and documents

Aryl O- and S-galactosides and lactosides as specific inhibitors of human galectins-1 and -3: Role of electrostatic potential at O-3

Phase transfer catalyzed reaction was used for the high yielding synthesis of aryl 1-thio-β-d-galacto- and lacto-pyranosides carrying a panel of substituents on the phenyl groups. Best galectin-1 inhibitors were simple p-nitrophenyl thiogalactoside 5a for

STEREOSELECTIVE SYNTHESES OF O- AND S-NITROPHENYL GLYCOSIDES. PART III. SYNTHESES IN THE &α-D-GALACTOPYRANOSE AND &α-MALTOSE SERIES

The action of p-nitrophenol penta-O-acetyl-β-D-galactopyranose in dichloromethane, in the presence of stannic tetrachloride gave p-nitrophenyl α-D-galactoside in fair yield.This technique failed when o-nitrophenol was used.Tetra-O-acetyl-β-D-galactopyranosyl and hepta-O-acetyl-β-maltosyl chlorides were converted to p- or o-nitrophenyl α-D-glycosides and p-nitrophenyl α-D-1-thioglycosides in good yield using hexamethylphosphoramide as a solvent and the sodium salt of the phenols as nucleophiles.The galactosides have been functionalized for further condensation at the C-4 position by selective benzoylation.

The mechanism of action of beta-galactosidase. Effect of aglycone nature and -deuterium substitution on the hydrolysis of aryl galactosides.

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