82-57-5

Basic information

• Product Name: 5H-Furo[3,2-g][1]benzopyran-5-one,4-methoxy-7-methyl-
• Synonyms: 5-Methoxy-2-methyl-6,7-furanochrome;5-Methoxy-2-methylfuranochromone;Desmethoxykhellin;NSC 100593;Visnagidin;Visnagine;4-Methoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one;Visnagin(6CI)
• CAS NO: 82-57-5
• Molecular Formula: C₁₃H₁₀O₄
• Molecular Weight: 230.2161
• EINECS: 201-430-3
• Product Categories: Chromones
• Mol File: 82-57-5.mol

Chemical Properties

• Melting Point: 139-142 °C
• Boiling Point: 378.2 °C at 760 mmHg
• Flash Point: 182.5 °C
• Appearance: beige fine crystalline powder
• Density: 1.308 g/cm³
• Vapor Pressure: 6.4E-06mmHg at 25°C
• Refractive Index: 1.613
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: 5H-Furo[3,2-g][1]benzopyran-5-one,4-methoxy-7-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 5H-Furo[3,2-g][1]benzopyran-5-one,4-methoxy-7-methyl-(82-57-5)
• EPA Substance Registry System: 5H-Furo[3,2-g][1]benzopyran-5-one,4-methoxy-7-methyl-(82-57-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RTECS: LV1420000
• Hazardous Substances Data: 82-57-5(Hazardous Substances Data)

Usage

Purification Methods

Crystallise visnagin from water. It is soluble in CHCl3 but slightly soluble in EtOH. [Aneja et al. Tetrahedron 3 230 1958, Beilstein 19 III/IV 2640.]

References

1) Liu et al. (2014), Visnagin protects against doxorubicin-induced cardiomyopathy through modulation of mitochondrial malate dehydrogenase; Sci. Transl. Med. 6 266ra170

InChI:InChI=1/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3

Upstream product

• 70097-62-0 7-chloromethyl-4-methoxy-furo[3,2-g]chromen-5-one 
• 96460-58-1 7-iodomethyl-4-methoxy-furo[3,2-g]chromen-5-one 
• 78633-80-4 6-allyl-7-hydroxy-5-methoxy-2-methylchromone 
• 855631-87-7 4-methoxy-7-(toluene-4-sulfonyloximethyl)-furo[3,2-g]chromen-5-one 
• 102474-27-1 6-allyl-5-methoxy-2-methyl-7-(toluene-4-sulfonyloxy)-chromen-4-one 
• 102078-44-4 6-allyl-5-hydroxy-2-methyl-7-(toluene-4-sulfonyloxy)-chromen-4-one 
• 478-79-5 Khellol 
• 484-27-5 5-acetyl-4-methoxybenzofuran-6-ol 
• 122822-90-6 1-(6-Ethoxy-4-methoxy-7-methylsulfanyl-benzofuran-5-yl)-ethanone 
• 122822-88-2 Acetic acid 6-ethoxy-7-methylsulfanyl-5-vinyl-benzofuran-4-yl ester 
• 122822-91-7 1-(6-Hydroxy-4-methoxy-7-methylsulfanyl-benzofuran-5-yl)-ethanone 
• 122822-89-3 6-Ethoxy-4-methoxy-7-methylsulfanyl-5-vinyl-benzofuran 
• 78633-78-0 4-allyloxy-2-hydroxy-3-iodo-6-methoxybenzoylacetone 
• 78633-79-1 7-allyloxy-8-iodo-5-methoxy-2-methylchromone 

Downstream Products

• 7338-51-4 7-hydroxy-5-methoxy-2-methyl-4-oxo-4H-chromene-6-carbaldehyde 
• 18646-74-7 5-formyl-4-hydroxy-6-methoxysalicylic acid 
• 138565-06-7 methyl 7-hydroxy-5-methoxy-2-methylchromone-6-carboxylate 
• 112649-26-0 6-hydroxy-4-methoxy-N-(4-methoxyphenyl)-5-<3-<(4-methoxyphenyl)amino>-1-oxo-2-butenyl>-7-benzofuransulfonamide 
• 112649-25-9 6-hydroxy-4-methoxy-N-(2-methylphenyl)-5-<3-<(2-methylphenyl)amino>-1-oxo-2-butenyl>-7-benzofuransulfonamide 
• 106911-45-9 4-methoxy-N-(2-methoxyphenyl)-7-methyl-5-oxo-5H-furo<3,2-g><1>benzopyran-9-sulfonamide 
• 106911-46-0 4-methoxy-N-(4-methoxyphenyl)-7-methyl-5-oxo-5H-furo<3,2-g><1>benzopyran-9-sulfonamide 
• 112649-24-8 4-methoxy-N-(3-methoxyphenyl)-7-methyl-5-oxo-5H-furo<3,2-g><1>benzopyran-9-sulfonamide 
• 106911-48-2 N-(4-bromophenyl)-4-methoxy-7-methyl-5-oxo-5H-furo<3,2-g><1>benzopyran-9-sulfonamide 
• 106911-47-1 N-(4-chlorophenyl)-4-methoxy-7-methyl-5-oxo-5H-furo<3,2-g><1>benzopyran-9-sulfonamide 
• 112649-23-7 N-(3-chlorophenyl)-4-methoxy-7-methyl-5-oxo-5H-furo<3,2-g><1>benzopyran-9-sulfonamide 
• 106911-43-7 4-methoxy-7-methyl-N-(2-methylphenyl)-5-oxo-5H-furo<3,2-g><1>benzopyran-9-sulfonamide 
• 106911-44-8 4-methoxy-7-methyl-N-(4-methylphenyl)-5-oxo-5H-furo<3,2-g><1>benzopyran-9-sulfonamide 
• 112649-22-6 4-methoxy-7-methyl-N-(3-methylphenyl)-5-oxo-5H-furo<3,2-g><1>benzopyran-9-sulfonamide 

Relevant articles and documents

SELECTIVE CLAISEN MIGRATION IN CHROMONES. A CONVENIENT SYNTHESIS OF THE LINEAR FURANOCHROMONES DESMETHOXYVISNAGIN, NORVISNAGIN, and VISNAGIN

A convenient synthesis of furanochromones, viz. 7-methyl-5H-furobenzopyran-5-one (desmethoxyvisnagin), 4-hydroxy-7-methyl-5H-furobenzopyran-5-one (norvisnagin), and 4-methoxy-7-methyl-5H-furobenzopyran-5-one (visnagin) is described.The synthesis utilises blocking the 8-position of the corresponding 7-allyloxychromone derivative with iodine, Claisen migration, followed by oxidation and subsequent cyclo-dehydration.