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3150-25-2, 3-Nitrophenyl-β-D- galactopyranoside, CAS:3150-25-2

3150-25-2,3-Nitrophenyl-β-D-galactopyranoside,
CAS:3150-25-2
C12H15NO8 / 301.25
MFCD00047517

3-Nitrophenyl b-D-galactopyranoside

3-Nitrophenyl β-D-galactopyranoside (ONPG) is a synthetic substrate that is widely used in the biochemical and pharmaceutical fields. It is a colorless, crystalline compound that is soluble in water and is commonly used for the detection of β-galactosidase activity in bacterial and cell cultures. This paper aims to provide an informative and persuasive piece of work on the topic of 3-Nitrophenyl β-D-galactopyranoside. The paper will cover various aspects of this compound, including its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Definition and Background:

3-Nitrophenyl β-D-galactopyranoside is also known as ONPG. It is a synthetic substrate commonly used for the detection of β-galactosidase activity in bacterial and cell cultures. It is a derivative of lactose and consists of a galactose molecule linked to a nitrophenyl group through a β-glycosidic bond. It was first discovered by Bourns and his colleagues in the 1950s and has since become a widely used compound in the biochemical and pharmaceutical industries.

Physical and Chemical Properties:

3-Nitrophenyl β-D-galactopyranoside is a colorless, crystalline compound that is soluble in water. It has a melting point of 205-208°C and a molecular weight of 301.24 g/mol. Its chemical formula is C12H15NO8.

Synthesis and Characterization:

Synthesis of ONPG is usually carried out by the reaction of galactose with 3-nitrophenol in the presence of an acid catalyst. The resulting compound is then purified by recrystallization and dried. The structure and purity of ONPG can be confirmed by various analytical techniques, including nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry.

Analytical Methods:

The activity of β-galactosidase in bacterial or cell cultures can be determined by measuring the amount of 3-nitrophenol released from ONPG. The reaction between β-galactosidase and ONPG releases a galactose molecule and a nitrophenyl group. The nitrophenyl group is then converted into 3-nitrophenol by alkaline hydrolysis, which can be measured spectrophotometrically at a wavelength of 420 nm.

Biological Properties:

ONPG is commonly used for the detection of β-galactosidase activity in bacterial and cell cultures. It is an inert substrate that does not interfere with the normal metabolic processes of the cells. It is also non-toxic to the cells at the concentrations used in the experiments.

Toxicity and Safety in Scientific Experiments:

ONPG is generally considered safe for use in scientific experiments. It is non-toxic and non-carcinogenic at the concentrations used in the experiments. However, proper handling and disposal procedures should be followed to avoid any potential hazards.

Applications in Scientific Experiments:

ONPG is widely used for the detection of β-galactosidase activity in bacterial and cell cultures. It is also used for the detection of lactose fermentation in bacterial cultures. It has been used in the study of gene expression, protein expression, enzyme kinetics, and bacterial metabolism.

Current State of Research:

Research on ONPG has been ongoing since its discovery in the 1950s. Numerous studies have been conducted on its properties, synthesis, and applications in various fields of research. The current state of research suggests that ONPG continues to be a valuable tool for the detection of β-galactosidase activity in bacterial and cell cultures.

Potential Implications in Various Fields of Research and Industry:

ONPG has potential implications in various fields of research and industry. It can be used in the detection of lactose fermentation in the dairy industry. It can also be used in the detection of β-galactosidase activity in clinical samples, such as blood and urine. In the pharmaceutical industry, ONPG can be used in the screening of potential drug candidates for β-galactosidase inhibitory activity.

Limitations and Future Directions:

One limitation of ONPG is that it is specific to the detection of β-galactosidase activity and cannot be used to detect other enzymes. Future directions of research could focus on the development of new synthetic substrates that can detect multiple enzymes. Other directions for future research could include the development of new analytical methods for the detection of ONPG and the study of its potential applications in biotechnology and nanotechnology.

In conclusion, 3-Nitrophenyl β-D-galactopyranoside (ONPG) is a synthetic substrate that is widely used in the biochemical and pharmaceutical fields. This paper has provided an informative and persuasive piece of work on ONPG, covering various aspects of this compound, including its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions. Understanding the properties and applications of ONPG can provide valuable insights into the detection of β-galactosidase activity in bacterial and cell cultures and can have potential implications in various fields of research and industry.

CAS Number3150-25-2
Product Name3-Nitrophenyl b-D-galactopyranoside
IUPAC Name(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(3-nitrophenoxy)oxane-3,4,5-triol
Molecular FormulaC12H15NO8
Molecular Weight301.25 g/mol
InChIInChI=1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-2-6(4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9+,10+,11-,12-/m1/s1
InChI KeyVCCMGHVCRFMITI-YBXAARCKSA-N
SMILESC1=CC(=CC(=C1)OC2C(C(C(C(O2)CO)O)O)O)[N+](=O)[O-]
Canonical SMILESC1=CC(=CC(=C1)OC2C(C(C(C(O2)CO)O)O)O)[N+](=O)[O-]
Isomeric SMILESC1=CC(=CC(=C1)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)[N+](=O)[O-]


CAS No: 3150-25-2 MDL No: MFCD00047517 Chemical Formula: C12H15NO8 Molecular Weight: 301.25


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