31525-76-5

Basic information

• Product Name: 5-methoxy-8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one
• Synonyms: 5-Methoxyseselin;2H,8H-Benzo[1,2-b:3,4-b']dipyran-2-one, 5-methoxy-8,8-dimethyl-
• CAS NO: 31525-76-5
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.2693
• Mol File: 31525-76-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 154-156 °C
• Boiling Point: 441.2°C at 760 mmHg
• Flash Point: 198.5°C
• Density: 1.225g/cm³
• Vapor Pressure: 5.53E-08mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: 5-methoxy-8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methoxy-8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one(31525-76-5)
• EPA Substance Registry System: 5-methoxy-8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one(31525-76-5)

Safety Data

• Hazardous Substances Data: 31525-76-5(Hazardous Substances Data)

Upstream product

• 31525-75-4 5-hydroxy-8,8-dimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 3067-10-5 7-hydroxy-5-methoxychromene-2-one 
• 32023-43-1 7-(1,1-dimethyl-prop-2-ynyloxy)-5-methoxy-chromen-2-one 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 164329-24-2 2,4-diacetoxyl-6-hydroxybenzaldehyde 
• 53277-19-3 2,4,6-triacetoxybenzaldehyde 
• 2732-18-5 5,7-dihydroxy-2H-chromen-2-one 
• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 53017-21-3 5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one 
• 76256-29-6 5,7-diacetoxy-8-(3'-methyl-2'-butenyl)coumarin 
• 29373-14-6 2,2-dimethylchromane-5,7-diol 

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.

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.

SYNTHESIS OF NEW PYRANOCOUMARINS

As a result of condensing 5,7-dihydroxy-4-methylcoumarin with dimethyl acetal-3-methylbuten-2-al, 4-methyl-5-hydroxyseseline, 4-methyldipetalolactone and 5-hydroxy-4,10,10-trimethyl-2H,8H-benzodipyran-2-one have been obtained.Condensation of 5,7-hydroxycoumarin with this acetal leads to 5-hydroxyseseline, dipetalolactone and 5-hydroxy-10,10-dimethyl-2H,8H-benzodipyran-2-one