3067-10-5

Basic information

• Product Name: 5-Methoxy-7-hydroxycoumarin
• Synonyms: 5-Methoxy-7-hydroxycoumarin
• CAS NO: 3067-10-5
• Molecular Formula: C₁₀H₈O₄
• Molecular Weight: 192.16812
• Mol File: 3067-10-5.mol

Chemical Properties

• Boiling Point: 429.9°Cat760mmHg
• Flash Point: 179.6°C
• Appearance: /
• Density: 1.377g/cm³
• Vapor Pressure: 5.39E-08mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: 5-Methoxy-7-hydroxycoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxy-7-hydroxycoumarin(3067-10-5)
• EPA Substance Registry System: 5-Methoxy-7-hydroxycoumarin(3067-10-5)

Safety Data

• Hazardous Substances Data: 3067-10-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H8O4/c1-13-8-4-6(11)5-9-7(8)2-3-10(12)14-9/h2-5,11H,1H3

Upstream product

• 91136-78-6 7-hydroxy-5-methoxy-2-oxo-2H-chromene-3-carboxylic acid 
• 101-38-2 2,6-dichloroquinone-4-chloroimide 
• 79326-04-8 5-Hydroxy-6-methoxycoumarin 
• 2732-18-5 5,7-dihydroxy-2H-chromen-2-one 
• 77-78-1 dimethyl sulfate 
• 2174-64-3 5-methoxyresorcinol 
• 623-47-2 propynoic acid ethyl ester 
• 4221-48-1 7-acetoxy-5-methoxy-chromen-2-one 
• 108-73-6 3,5-dihydroxyphenol 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 164329-24-2 2,4-diacetoxyl-6-hydroxybenzaldehyde 
• 53277-19-3 2,4,6-triacetoxybenzaldehyde 
• 3519-76-4 2,4-dihydroxy-6-methoxybenzaldehyde 
• 471-25-0 Propiolic acid 

Downstream Products

• 31525-76-5 5-methoxyseselin 
• 30779-96-5 5-methoxy-7-O-(3,3-dimethylallyl)coumarin 
• 484-20-8 bergapten 
• 84-99-1 xanthoxyletin 
• 95-57-8 2-monochlorophenol 
• 2107-76-8 4-methyl-5,7-dihydroxycoumarin 

Relevant articles and documents

A catalyst-free one-pot construction of skeletons of 5-methoxyseselin and alloxanthoxyletin in water

In refluxing water and without an additional catalyst, electron-rich phenols could react with alkynoic acids or alkynoates to provide coumarin structures. The skeletons of two natural pyranocoumarins, 5-methoxyseselin and alloxanthoxyletin, could be constructed (total yield up to 76%) in an aqueous multicomponent reaction in which isoprenyl acetate, propiolic acid, and phloroglucinol were simply mixed and refluxed in water.

Efficient total synthesis of 5-methoxypsoralen

A rapid and efficient synthesis of 5-methoxypsoralen, furocoumarin commonly used in dermatology for the treatment by PUVA therapy of skin diseases, is described using cheap and easily available starting materials. An alternative method to synthesize 7-(2-oxoethoxy)coumarin, the key step to generate the furan ring, is suggested. Georg Thieme Verlag Stuttgart.

An efficient synthesis of bergapten

An efficient synthesis of the linear furanocoumarin, bergapten, is reported. In order to avoid the formation of the angular furanocoumarin, we have adopted iodine as protecting group at the 8 position of the coumarin ring.

Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a net C-H insertion

A strategy to achieve ortho substitution of phenols initiated by an ortho-palladation to create coumarins was examined. Indeed, treatment of alkynoates with electron-rich phenols in the presence of a palladium catalyst and an acid does generate coumarins. The scope of the reaction with respect to the phenol and the alkynoates is defined. With unsymmetrical aromatic substrates, generally good regioselectivity that reflects the HOMO coefficients can be observed. In the course of these studies, numerous important naturally occurring coumarins have been synthesized, including fraxinol methyl ether, ayapin, herniarin, xanthoxyletin, and alloxanthoxyletin. The fact that a Pd(0) is the precatalyst rather than a Pd(+2) species and that an acid that reduces Pd(+2) salts, formic acid, functions better than other carboxylic acids raises doubts about the initial working hypothesis. A novel mechanism involving a palladium phenoxide formed from a hydridopalladium carboxylate and phenol is invoked to rationalize the results.

Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents

To explore the structural requirements of (+)-cis-khellactone derivatives as novel anti-HIV agents, 24 monosubstituted 3',4'-di-O-(S)- camphanoyl-(+)-cis-khellactone (DCK) derivatives were synthesized asymmetrically. These compounds included 4 isomeric monomethoxy analogues (3- 6), 4 isomeric monomethyl analogues (7-10), 4 4-alkyl/aryl-substituted analogues (11-14), and 12 4-methyl-(+)-cis-khellactone derivatives (15-26) with varying 3',4'-substituents. These (+)-cis-khellactone derivatives were screened against HIV-1 replication in acutely infected H9 lymphocytes. The results demonstrated that the (3'R,4'R)-(+)-cis-khellactone skeleton, two (S)-(-)-camphanoyl groups at the 3'- and 4'-positions, and a methyl group on the coumarin ring, except at the 6-position, were optimal structural moieties for anti-HIV activity. 3-Methyl- (7), 4-methyl- (8), and 5-methyl- (9) 3',4'- di-O-(S)-camphanoyl-(3'R,4'R)-(+)-cis-khellactone showed EC50 and therapeutic index values of -5 μM and >2.15 x 106, respectively, in H9 lymphocytes, which are much better than those of DCK and AZT in the same assay. Furthermore, 8 and 9 also showed potent inhibitory activity against HIV-1 replication in the CEM-SS cell line, and most monosubstituted DCK analogues were less toxic than DCK in both assays.

Anti-AIDS agents - XXVIII. Synthesis and anti-HIV activity of methoxy substitute 3',4'-di-O-(-)-Camphanoyl-(+)-cis-Khellactone (DCK) analogues

Four isomeric methoxy substituted DCK analogues (3-6) were asymmetrically synthesized from different starting materials. 5-Methoxy-3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (5) exhibited extremely potent anti-HIV activity against HIV-1 replication in H9 lymphocyte cells with EC50 and therapeutic index values of 0.00038 μM and >402,632, respectively, which are better than those of DCK and AZT in this assay.

Natural Product Chemistry. Part 121. Synthesis of Dicoumarinyl Ethers with the Structures Proposed for Fatagarine and Oreojasmine

Synthesis of the 7,8'-dicoumarinyl ethers: 7-methoxy-7',8-oxydicoumarin and 6,7-dimethoxy-7',8-oxydicoumarin, established that the structures of fatagarine and oreojasmine for which these two structures have been proposed, have to be revised.Synthesis of 7-methoxy-5,7'-oxydicoumarin and 8-methoxy-7,7'-oxydicoumarin exclude the possibility of these dicoumarinyl ether structures for fatagarine. - Keywords: Dicoumarinyl ethers; 6,7-Dimethoxy-7',8-oxydicoumarin; Fatagarine; 7-Methoxy-5,7'-oxydicoumarin; 8-Methoxy-7,7'-oxydicoumarin; 7-Methoxy-7',8-oxydicoumarin; Oreojasmine; Ruta oreojasme