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: 2024-11-05 11:59:05
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) |
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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