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HomeProduct name list2-Nitrophenyl-beta-D-galactopyranoside

2-Nitrophenyl-beta-D-galactopyranoside

Synonym(s):o-Nitrophenyl β-D-galactopyranoside;o-Nitrophenyl-β-D-galactopyranoside - CAS 369-07-3 - Calbiochem;o-NPG;ONPG;ONPG 

  • CAS NO.:369-07-3
  • Empirical Formula: C12H15NO8
  • Molecular Weight: 301.25
  • MDL number: MFCD00063255
  • EINECS: 206-716-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-10-11 17:37:18
2-Nitrophenyl-beta-D-galactopyranoside Structural

What is 2-Nitrophenyl-beta-D-galactopyranoside?

Description

2-Nitrophenyl-β-D-galactopyranoside (ONPG) is a colorimetric and spectrophotometric substrate for detecting β-galactosidase activity. This compound is usually colorless. However, if β-galactosidase is present, it hydrolyzes the ONPG molecule into galactose and ortho-nitrophenol. The latter compound has a yellow color that can be used to check for enzyme activity utilizing a colorimetric assay (at 420 nm wavelength). β-Galactosidase is required for lactose utilization, so the intensity of the color produced can be used to measure the enzymatic rate. Though ONPG mimics lactose and is hydrolyzed by β-galactosidase, it cannot act as an inducer for the lac operon. Without another lactose analog that can act as an inducer, such as isopropyl β-D-1-thiogalactopyranoside (IPTG), β-galactosidase will not be transcribed and ONPG will not be hydrolyzed.

Chemical properties

White Crystalline Solid

The Uses of 2-Nitrophenyl-beta-D-galactopyranoside

2-Nitrophenyl-beta-D-galactopyranoside is a β-Galactosidase substrate for colorimetric and EIA applications; counterpart of widely employed pNPP/alkaline phosphatase substrate.

What are the applications of Application

2-Nitrophenyl b-D-galactopyranoside is a β-galactosidase substrate for colorimetric and EIA applications

Definition

ChEBI: A beta-D-galactoside having a 2-nitrophenyl substituent at the anomeric position.

General Description

ONPG (2-Nitrophenyl β-D-galactopyranoside) is a colorimetric substrate for β-galactosidase.

Biochem/physiol Actions

β-galactosidase, breaks down lactose into galactose and glucose. β-Galactosidase is not lactose specific and can act on simple galactosides. 2-Nitrophenyl β-D-galactopyranoside hydrolysis results in the release of galactose and a yellow chromogenic compound. The test substrate does not depend on an induced or constitutive permease enzyme to enter the cell, therefore reactions are rapid and occur within a 24-hour period.

Purification Methods

Purify 2-nitrophenyl--D-galactopyranoside by recrystallisation from EtOH. [Seidman & Link J Am Chem Soc 72 4324 1950, Snyder & Link J Am Chem Soc 75 1758 1953]. It is a chromogenic substrate for -galactosidases [Jagota et al. J Food Sci 46 161 1981]. [Beilstein 17/7 V 52.]

Properties of 2-Nitrophenyl-beta-D-galactopyranoside

Melting point: 186-193 °C (dec.)
Boiling point: 442.39°C (rough estimate)
alpha  -70 º (c=1, H2O)
Density  1.3709 (rough estimate)
refractive index  -68.8 ° (C=1, H2O)
storage temp.  2-8°C
solubility  DMSO (Slightly), Water (Slightly, Heated, Sonicated)
form  Powder
pka 12.69±0.70(Predicted)
color  White to very slightly yellow
optical activity [α]20/D 70±1°, c = 1% in H2O
Water Solubility  Soluble in water.
BRN  92207
CAS DataBase Reference 369-07-3(CAS DataBase Reference)
NIST Chemistry Reference Galactopyranoside, o-nitrophenyl, beta-d-(369-07-3)

Safety information for 2-Nitrophenyl-beta-D-galactopyranoside

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P312:Call a POISON CENTER or doctor/physician if you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P403+P233:Store in a well-ventilated place. Keep container tightly closed.

Computed Descriptors for 2-Nitrophenyl-beta-D-galactopyranoside

InChIKey KUWPCJHYPSUOFW-RMPHRYRLSA-N

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