7493-95-0 Usage
Description
4-NITROPHENYL-ALPHA-D-GALACTOPYRANOSIDE, also known as p-Nitrophenyl α-D-Galactopyranoside (CAS# 7493-95-0), is a compound characterized by an alpha-D-galactopyranoside with a 4-nitrophenyl substituent at the anomeric position. It is an off-white crystalline solid and is primarily used in organic synthesis.
Uses
Used in Organic Synthesis:
4-NITROPHENYL-ALPHA-D-GALACTOPYRANOSIDE is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of complex molecules, particularly in the pharmaceutical and chemical industries.
Used in Analytical Chemistry:
In the field of analytical chemistry, 4-NITROPHENYL-ALPHA-D-GALACTOPYRANOSIDE is used as a substrate for the detection and quantification of specific enzymes, such as beta-galactosidase. The hydrolysis of this compound by the enzyme results in the release of the yellow 4-nitrophenol, which can be easily measured and used to determine enzyme activity.
Used in Research and Development:
4-NITROPHENYL-ALPHA-D-GALACTOPYRANOSIDE is also utilized in research and development for studying the mechanisms of enzyme-catalyzed reactions and the development of new catalysts or inhibitors for various biological processes. Its application in this field aids in advancing our understanding of enzyme function and the design of novel therapeutic agents.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-NITROPHENYL-ALPHA-D-GALACTOPYRANOSIDE is used as a key component in the development of new drugs targeting enzyme-related diseases. Its unique structure and reactivity make it a valuable tool for designing and testing potential drug candidates, ultimately contributing to the discovery of novel therapeutics.
Purification Methods
Purify 4-nitrophenyl--D-galactopyranoside by recrystallisation from H2O or aqueous EtOH. The monohydrate has m 85o which resolidifies and melts again at 151-152o (the hemihydrate), then resolidifies again and melts at 173o to give the anhydrous form. Drying the monohydrate at 60o yields the hemihydrate, and drying at 100o gives the anhydrous compound. The tetraacetate has m 147o after drying at 100o. [Jermyn Aust J Chem 15 569 1962, Helfreich & Jung Justus Liebigs Ann Chem 589 77 1954.] It is a substrate for galactosidase [Dangelmaier & Holmsen Anal Biochem 104 182 1980]. [Beilstein 17/7 V 55.]
Check Digit Verification of cas no
The CAS Registry Mumber 7493-95-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,4,9 and 3 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 7493-95:
(6*7)+(5*4)+(4*9)+(3*3)+(2*9)+(1*5)=130
130 % 10 = 0
So 7493-95-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9+,10+,11-,12+/m1/s1
7493-95-0Relevant articles and documents
Syntheses of p-nitrophenyl 3- and 4-thio-β-d-glycopyranosides
Chen, Hong-Ming,Withers, Stephen G.
experimental part, p. 2596 - 2604 (2011/01/12)
Thioglycosides have proved to be useful, enzymatically stable analogs of glycosides for structural and mechanistic studies and their synthesis is considerably simplified through the use of thioglycoligases. As part of an investigation into the use of thio
STEREOSELECTIVE SYNTHESES OF O- AND S-NITROPHENYL GLYCOSIDES. PART III. SYNTHESES IN THE &α-D-GALACTOPYRANOSE AND &α-MALTOSE SERIES
Apparu, Maecel,Blanc-Muesser, Michele,Defaye, Jacques,Driguez, Hugues
, p. 314 - 320 (2007/10/02)
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.
