131086-92-5

Basic information

• Product Name: 3,4-dihydroxy-6H-benzo[c]chromen-6-one
• Synonyms: 6H-Dibenzo(b,d)pyran-6-one, 3,4-dihydroxy-
• CAS NO: 131086-92-5
• Molecular Formula: C₁₃H₈O₄
• Molecular Weight: 228.2002
• Mol File: 131086-92-5.mol

Chemical Properties

• Boiling Point: 461.9°C at 760 mmHg
• Flash Point: 186.5°C
• Density: 1.516g/cm³
• Vapor Pressure: 3.75E-09mmHg at 25°C
• Refractive Index: 1.717
• CAS DataBase Reference: 3,4-dihydroxy-6H-benzo[c]chromen-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dihydroxy-6H-benzo[c]chromen-6-one(131086-92-5)
• EPA Substance Registry System: 3,4-dihydroxy-6H-benzo[c]chromen-6-one(131086-92-5)

Safety Data

• Hazardous Substances Data: 131086-92-5(Hazardous Substances Data)

Upstream product

• 5150-42-5 2,3-dimethoxyphenol 
• 103681-98-7 2-diisopropylaminocarbonylphenylboronic acid 
• 10385-36-1 2,3,4-trimethoxybromobenzene 
• 7154-66-7 2-bromobenzoic acid chloride 
• 133730-27-5 N,N-Diisopropyl-2',3',4'-trimethoxy-2-biphenylcarboxamide 

Relevant articles and documents

Dna gyrase inhibitory activity of ellagic acid derivatives

Ellagic acid was found to inhibit E. coli DNA gyrase supercoiling with approximately the same potency as nalidixic acid. Tricyclic analogs of ellagic acid, which vary in the number and position of the hydroxy soups as well as their replacement with haloge

Tricyclic polyhydroxylic tyrosine kinase inhibitors

Certain tricyclic polyhydroxylic compounds, and their pharmaceutically-acceptable salts, are inhibitors of tyrosine kinase enzymes, and so are useful for the control of tyrosine kinase dependent diseases (e.g., cancer, atherosclerosis).

Ellagic acid analogues

Synthetic novel ellagic acid congeners of the formula: STR1 wherein: R1 is --H, --OH or --OR'; R2 is --H, --OH or --OR'; R3 is --H, --OH or --OR'; R4 is --H, --OH or --OR'; R5 is --H, --OH or --OR'; R6 is --H, --OH or --OR'; R' is lower alkyl having 1 to 8 carbon atoms or --CH2 --Ar; Ar is phenyl or substituted phenyl, and at least one of R1, R2, R3, R4, R5 and R6 is other than --H. The above compounds and 6H-dibenzo[b,d]pyran-6-one are useful for inhibiting mutagenic activity in living cells.

Sequential Directed Ortho Metalation-Boronic Acid Cross-Coupling Reactions. A General Regiospecific Route to Oxygenated Dibenzopyran-6-ones Related to Ellagic Acid

A general regiospecific synthesis of dibenzopyran-6-one derivatives 1a,c and 8a-i related to ellagic acid is described (Scheme I, Table I).The sequence involves directed ortho metalation-boronation of benzamides 4 to give the arylboronic acids 5, which, upon palladium-catalyzed cross-coupling with alkoxybromobenzenes 6 leads to the biphenylamides 7.BBr3 demethylation followed by acid-catalyzed cyclization affords pyranone 8.In this manner, the naturally occurring dibenzopyranones 1a, autumnariol (1c), and the heterocyclic analogue 13 (Scheme III) were efficiently prepared.