2732-18-5

Basic information

• Product Name: 5,7-DIHYDROXYCOUMARIN
• Synonyms: 5,7-DIHYDROXYCOUMARIN;2H-1-Benzopyran-2-one, 5,7-dihydroxy-;5,7-Dihydroxy-2H-1-benzopyran-2-one;5,7-Dihydroxy-2H-chromen-2-one
• CAS NO: 2732-18-5
• Molecular Formula: C₉H₆O₄
• Molecular Weight: 178.14
• Mol File: 2732-18-5.mol
• Article Data: 21

Chemical Properties

• Melting Point: 280 °C
• Boiling Point: 506.402 °C at 760 mmHg
• Flash Point: 216.911 °C
• Appearance: /
• Density: 1.563 g/cm³
• Vapor Pressure: 7.06E-11mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.18±0.20(Predicted)
• CAS DataBase Reference: 5,7-DIHYDROXYCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-DIHYDROXYCOUMARIN(2732-18-5)
• EPA Substance Registry System: 5,7-DIHYDROXYCOUMARIN(2732-18-5)

Safety Data

• Hazardous Substances Data: 2732-18-5(Hazardous Substances Data)

Usage

Uses

5,7-Dihydroxy-2H-chromen-2-one can be used to prepare UV-?responsive coumarin controlled release and self-?repairing antifouling paint.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 41, p. 4542, 1998 DOI: 10.1021/jm981032oJournal of Heterocyclic Chemistry, 2, p. 91, 1965 DOI: 10.1002/jhet.5570020116

InChI:InChI=1/C9H6O4/c10-5-3-7(11)6-1-2-9(12)13-8(6)4-5/h1-4,10-11H

Upstream product

• 21524-17-4 5,7-diacetoxyl-2-chromenone 
• 108-73-6 3,5-dihydroxyphenol 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 84740-26-1 6-(C-β-D-glucosyl)-5,7-dihydroxycoumarin 
• 623-47-2 propynoic acid ethyl ester 
• 471-25-0 Propiolic acid 
• 882685-19-0 (E)-3-(2,4,6-trihydroxyphenyl)acrylic acid octyl ester 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 1185256-07-8 ethyl (2E)-3-(2,4,6-trihydroxyphenyl)arylate 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 17820-07-4 7-hydroxy-8-(1,1-dimethylallyl)alloxanthyletin 
• 84740-26-1 6-(C-β-D-glucosyl)-5,7-dihydroxycoumarin 
• 33044-74-5 bruceol 
• 524-12-9 wedelolactone 
• 115623-32-0 1,8,9-tris(benzyloxy)-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one 
• 23053-61-4 5,7-dihydroxycoumarin 7-methyl ether 
• 21524-17-4 5,7-diacetoxyl-2-chromenone 
• 35590-41-1 5-(isopent-2'-enyloxy)-7-methoxycoumarin 
• 31525-76-5 5-methoxyseselin 
• 33899-44-4 5-(2-enyl-3-methylbut)oxy-7-hydroxycoumarin 
• 130364-30-6 7-hydroxy-5',5a'-dimethylpyrano[2',3'-f]-(2H)-chromen-2-one 
• 57601-61-3 6,6,10,10-tetramethyl-2H,6H,10H-benzo<1,2-b:13,4-b':5,6-b''>tripyran-2-one 
• 31525-75-4 5-hydroxy-8,8-dimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one 
• 108-73-6 3,5-dihydroxyphenol 

Relevant articles and documents

Evaluation of coumarin and neoflavone derivatives as HCV NS5B polymerase inhibitors

Coumarins and coumestans represent an important family of compounds with diverse pharmacological properties. We recently identified coumestans as novel inhibitors of hepatitis C virus NS5B polymerase and predicted their binding in thumb pocket-1 (TP-1) of NS5B. As the coumarins are structurally related to coumestans by virtue of their common A- and B-rings, we postulated them to also exhibit similar binding interaction with NS5B and inhibit its polymerase function. We therefore investigated 24 coumarin and neoflavone derivatives as candidate NS5B inhibitors and identified 14 compounds inhibiting NS5B polymerase activity with IC50 values between 17 and 63 μm. Of these, the newly synthesized 6,8-diallyl-5,7-dihydroxycoumarin (8a) was produced in three steps in high chemical yield from floroglucinol and found to be the most potent of this series, exhibiting activity similar to the reference coumestan LQB-34. The binding site of 8a was mapped to TP-1 of NS5B by counter screening against P495L NS5B mutant, employed as a screen for TP-1 site binders. NS5B-TP-1-8a interaction map provided insight into 8a binding and offered clues for future SAR optimization.

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Biomimetic Synthetic Studies on the Bruceol Family of Meroterpenoid Natural Products

A biomimetic approach to total synthesis can offer several benefits, including the development of cascade reactions for the rapid generation of molecular complexity, and guidance in the structure revision of old natural products and the anticipation of ne

Difluoromethylthiolation of Phenols and Related Compounds with a HF2CSO2Na/Ph2PCl/Me3SiCl System

A novel HF2CSO2Na/Ph2PCl/Me3SiCl system is disclosed for the late-stage direct difluoromethylthiolation of Csp2 and Csp3 nucleophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF2H compounds in good yields. Other substrates such as indoles, pyrroles, pyrazoles, enamines, ketones, and β-keto esters were also transformed to corresponding SCF2H products in good yields. The late-stage direct difluoromethylthiolation of a number of natural products and pharmaceutically attractive molecules was also achieved.

Ytterbium triflate promoted coupling of phenols and propiolic acids: Synthesis of coumarins

Coumarins are a well-known class of natural occurring and semi-synthetic products with reported important and effective pharmacological activities. In this Letter an improved method for the chemical synthesis of such compounds is described. Coumarins have been obtained in good to excellent yields under microwave irradiation and solvent-free conditions in a short time from differently substituted phenols and propiolic acids used as starting materials in the presence of Yb(OTf)3 hydrate 10% mol as the catalyst.