23053-61-4

Usage

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

Upstream product

• 7380-39-4 5-geranyloxy-7-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 
• 471-25-0 Propiolic acid 
• 108-73-6 3,5-dihydroxyphenol 
• 74-88-4 methyl iodide 

Downstream Products

• 487-06-9 Limettin 
• 35590-41-1 5-(isopent-2'-enyloxy)-7-methoxycoumarin 
• 7380-39-4 5-geranyloxy-7-methoxycoumarin 

Relevant academic research and scientific papers

Structures of antimutagenic constituents in the peels of Citrus limon

The methanolic extracts from the peels of Citrus limon were found to show antimutagenic effects against 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole, and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the Ames test. From the methanolic extracts, four new coumarins (wakayamalimonol A–D) and a new furanocoumarin (wakayamalimonol E) were isolated together with fifteen known compounds. The absolute stereostructures of the new compounds were determined by chemical synthesis and the modified Mosher’s method. Among the isolated constituents, coumarins, furanocoumarins, and limonoids showed antimutagenic effects in the Ames test. One of the major constituent, limonin, showed significant antimutagenic effects against mitomycinC and PhIP in the micronucleus test in vivo.

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.

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.

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