Welcome: Chemsynlab ,carbohydrate chemistry
Language: Chinese ∷  English

25775-97-7, 2,4-Dinitrophenyl b-D-glucopyranoside

Cas:25775-97-7,
2,4-Dinitrophenyl b-D-glucopyranoside
C12H14N2O10 / 346.25

2,4-Dinitrophenyl b-D-glucopyranoside

2,4-Dinitrophenyl-beta-D-glucopyranoside is a chromogenic substrate used to assay enzymes, such as glucosidases. These enzymes catalyze the hydrolysis of glycosidic bonds in sugars.

2',4'-Dinitrophenylglucopyranoside (DNPG) is a chemical compound commonly used in biochemical tests to identify the presence of reducing sugars. DNPG is a yellow crystalline powder that is soluble in water and ethanol. It is also known as 2,4-dinitrophenyl-D-glucoside.

DNPG was first synthesized by S. Reichardt and W. Grasser in 1933. It is a derivative of glucose that reacts with aldehydes and ketones to produce a yellow-colored compound. DNPG is widely used in the laboratory as a reagent for the detection of glucose and other reducing sugars.

Physical and Chemical Properties:

DNPG has the chemical formula C12H14N2O9 and a molecular weight of 346.2 g/mol. It is a yellow crystalline powder that melts at 210-211°C. The boiling point of DNPG is 582.9°C at 760 mmHg. It is soluble in water, ethanol, acetone, and chloroform.

Synthesis and Characterization:

DNPG can be synthesized by the reaction of glucose and 2,4-dinitrophenylhydrazine in the presence of acetic acid. The product is then purified by recrystallization. The structure of DNPG can be confirmed by NMR spectroscopy and X-ray crystallography.

Analytical Methods:

DNPG is commonly used in biochemical tests to identify the presence of reducing sugars in a sample. The test involves adding DNPG to the sample and then heating it, which causes the formation of a yellow-colored compound. The intensity of the color is proportional to the amount of reducing sugar present in the sample.

Biological Properties:

DNPG is not known to have any significant biological activity. It is used primarily as a biochemical reagent.

Toxicity and Safety in Scientific Experiments:

DNPG is considered to be non-toxic in small amounts. However, it may cause skin and eye irritation. It is important to handle DNPG with care and to follow appropriate safety protocols when working with the compound.

Applications in Scientific Experiments:

DNPG is widely used in biochemical assays to identify the presence of reducing sugars in a sample. It is also used in the study of enzymatic reactions and carbohydrate metabolism.

Current State of Research:

DNPG is a well-established biochemical reagent that has been widely used in scientific research for many years. There is ongoing research into new applications for DNPG in areas such as enzymology and carbohydrate chemistry.

Potential Implications in Various Fields of Research and Industry:

DNPG has potential applications in various fields of research and industry, including biotechnology, pharmaceuticals, and food science. It could be used to develop new assays for the detection of reducing sugars and to study the metabolism of carbohydrates in living systems.

Limitations and Future Directions:

One limitation of DNPG is that it is not specific to glucose and can react with other reducing sugars. Researchers are exploring ways to improve the specificity of DNPG-based assays. Future directions for research include the development of new DNPG derivatives with improved properties, and the discovery of new applications for DNPG in the fields of enzymology and carbohydrate chemistry.

In conclusion, 2',4'-Dinitrophenylglucopyranoside is a well-known biochemical reagent widely used to identify the presence of reducing sugars in a sample. It has numerous applications in scientific research and industry, including biotechnology, pharmaceuticals, and food science. Ongoing research is focused on improving the specificity of DNPG-based assays and developing new applications for the compound in the fields of enzymology and carbohydrate chemistry. With continued research, DNPG may have the potential to make significant contributions to these fields.

CAS Number25775-97-7
Product Name2',4'-Dinitrophenylglucopyranoside
IUPAC Name(3R,4S,5S,6R)-2-(2,4-dinitrophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular FormulaC12H14N2O10
Molecular Weight346.25 g/mol
InChIInChI=1S/C12H14N2O10/c15-4-8-9(16)10(17)11(18)12(24-8)23-7-2-1-5(13(19)20)3-6(7)14(21)22/h1-3,8-12,15-18H,4H2/t8-,9-,10+,11-,12?/m1/s1
InChI KeyXAJUPNGKLHFUED-OZRWLHRGSA-N
SMILESC1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
Synonyms2',4'-dinitrophenyl-beta-D-glucopyranoside, 2',4'-dinitrophenylglucopyranoside, 2,4-DNPG
Canonical SMILESC1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
Isomeric SMILESC1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])OC2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O


INQUIRY

Scan the qr codeClose
the qr code