53391-72-3

Basic information

• Product Name: 6-CHLORO-7-HYDROXY-4-PHENYL-2H-CHROMEN-2-ONE
• Synonyms: Coumarin,6-chloro-7-hydroxy-4-phenyl- (7CI); Umbelliferone, 6-chloro-4-phenyl- (6CI);6-Chloro-7-hydroxy-4-phenylcoumarin
• CAS NO: 53391-72-3
• Molecular Formula: C₁₅H₉ClO₃
• Molecular Weight: 272.68
• Mol File: 53391-72-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 469.2°Cat760mmHg
• Flash Point: 237.5°C
• Appearance: /
• Density: 1.437g/cm³
• Vapor Pressure: 2E-09mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: 6-CHLORO-7-HYDROXY-4-PHENYL-2H-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-7-HYDROXY-4-PHENYL-2H-CHROMEN-2-ONE(53391-72-3)
• EPA Substance Registry System: 6-CHLORO-7-HYDROXY-4-PHENYL-2H-CHROMEN-2-ONE(53391-72-3)

Safety Data

• Hazardous Substances Data: 53391-72-3(Hazardous Substances Data)

Usage

Class of Organic Compounds

Chromones

Functional Groups

Chloro group at position 6, Hydroxy group at position 7, Phenyl group at position 4
Potential Pharmacological Activities
Applications in Medicinal Chemistry and Drug Development

InChI:InChI=1/C15H9ClO3/c16-12-6-11-10(9-4-2-1-3-5-9)7-15(18)19-14(11)8-13(12)17/h1-8,17H

Upstream product

• 95-88-5 4-Chlororesorcinol 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Downstream Products

• 1417989-51-5 6-chloro-4-methylumbelliferyl-β-cellobioside 

Relevant articles and documents

Rational design, synthesis, evaluation and enzyme - Substrate structures of improved fluorogenic substrates for family 6 glycoside hydrolases

Methylumbelliferyl-β-cellobioside (MUF-G2) is a convenient fluorogenic substrate for certain β-glycoside hydrolases (GH). However, hydrolysis of the aglycone is poor with GH family 6 enzymes (GH6), despite strong binding. Prediction of the orientation of the aglycone of MUF-G2 in the +1 subsite of Hypocrea jecorina Cel6A by automated docking suggested umbelliferyl modifications at C4 and C6 for improved recognition. Four modified umbelliferyl-β-cellobiosides [6-chloro-4-methyl- (ClMUF); 6-chloro-4-trifluoromethyl- (ClF3MUF); 4-phenyl- (PhUF); 6-chloro-4-phenyl- (ClPhUF)] were synthesized and tested with GH6, GH7, GH9, GH5 and GH45 cellulases. Indeed the rate of aglycone release by H. jecorina Cel6A was 10-150 times higher than with MUF-G2, although it was still three orders of magnitude lower than with H. jecorina Cel7B. The 4-phenyl substitution drastically reduced the fluorescence intensity of the free aglycone, while ClMUF-G2 could be used for determination of kcat and KM for H. jecorina Cel6A and Thermobifida fusca Cel6A. Crystal structures of H. jecorina Cel6A D221A mutant soaked with the MUF-, ClMUF- and ClPhUF-β-cellobioside substrates show that the modifications turned the umbelliferyl group 'upside down', with the glycosidic bond better positioned for protonation than with MUF-G2. 2012 The Authors Journal compilation