26213-83-2

Basic information

• Product Name: 5,7-DIMETHOXY-2-METHYL-CHROMEN-4-ONE
• Synonyms: 5,7-DIMETHOXY-2-METHYL-CHROMEN-4-ONE
• CAS NO: 26213-83-2
• Molecular Formula: C₁₂H₁₂O₄
• Molecular Weight: 220.22128
• Mol File: 26213-83-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 378.9°C at 760 mmHg
• Flash Point: 170.4°C
• Appearance: /
• Density: 1.202g/cm³
• Vapor Pressure: 6.07E-06mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: 5,7-DIMETHOXY-2-METHYL-CHROMEN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-DIMETHOXY-2-METHYL-CHROMEN-4-ONE(26213-83-2)
• EPA Substance Registry System: 5,7-DIMETHOXY-2-METHYL-CHROMEN-4-ONE(26213-83-2)

Safety Data

• Hazardous Substances Data: 26213-83-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H12O4/c1-7-4-9(13)12-10(15-3)5-8(14-2)6-11(12)16-7/h4-6H,1-3H3

Upstream product

• 65547-60-6 1-(2-hydroxy-4, 6-dimethoxyphenyl)butane-1,3-dione 
• 1013-69-0 eugenin 
• 77-78-1 dimethyl sulfate 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 500-99-2 3,5-dimethoxyphenol 
• 121781-82-6 5-(1-methoxyethylene) Meldrum's acid 
• 480-27-3 1-Methyl-3-(2',4',6'-trimethoxyphenyl)propan-1,3-dione 

Downstream Products

• 1407546-95-5 C₂₅H₂₈N₂O₄ 
• 1407546-96-6 C₂₄H₂₈N₂O₄ 
• 1382529-04-5 2-[2-(4-(cyclopropylmethoxy)phenyl)vinyl]-5,7-dimethoxychromen-4-one 
• 1382528-88-2 2-[2-(4-bromophenyl)vinyl]-5,7-dimethoxychromen-4-one 
• 1382528-89-3 5,7-dimethoxy-2-[2-(4-methoxyphenyl)vinyl]chromen-4-one 
• 1382529-03-4 5,7-dimethoxy-2-[2-(4-nitrophenyl)vinyl]chromen-4-one 
• 1382528-87-1 2-[2-(4-chlorophenyl)vinyl]-5,7-dimethoxychromen-4-one 
• 1382528-86-0 2-[2-(4-fluorophenyl)vinyl]-5,7-dimethoxychromen-4-one 
• 1382529-00-1 2-[2-(3,5-dimethoxyphenyl)vinyl]-5,7-dimethoxychromen-4-one 
• 1382529-02-3 5,7-dimethoxy-2-[2-(4-trifluoromethoxyphenyl)vinyl]chromen-4-one 
• 480-34-2 eugenin 
• 1401428-09-8 (E)-5,7-hydroxy-2-(3,4,5-trihydroxystyryl)-4H-chromen-4-one 
• 1401428-04-3 (E)-5,7-dimethoxy-2-(3,4,5-trimethoxystyryl)-4H-chromen-4-one 

Relevant articles and documents

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Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent

A series of novel 6-methoxy-2-(piperazin-1-yl)-4H-chromen-4-one and 5,7-dimethoxy-2-(piperazin-1-ylmethyl)-4H-chromen-4-one derivatives of biological interest were prepared and screened for their pro-inflammatory cytokines (TNF-α and IL-6) and antimicrobial activity (antibacterial and antifungal). Among all the compound screened (5a-j and 10k-t), the compounds 5c, 5g, 5h, 10l, 10m, 10n and 10r found to have promising anti-inflammatory activity (up to 65-87% TNF-α and 70-93% IL-6 inhibitory activity) at concentration of 10 μM with reference to standard dexamethasone (71% TNF-a and 84% IL-6 inhibitory activities at 1 μM) while the compounds 5b, 5i, 5j, 10s and 10t found to be potent antimicrobial agent showing even 2 to 2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 μg/mL.

Yb(OTf)3-catalyzed reactions of 5-alkylidene Meldrum's acids with phenols: One-pot assembly of 3,4-dihydrocoumarins, 4-chromanones, coumarins, and chromones

The Yb(OTf)3-catalyzed annulation reactions of phenols with 5-alkylidene Meldrum's acids enabled the synthesis of structurally diverse heterocycles in high isolated yields. A series of 4-substituted 3,4-dihydrocoumarins, 2,2-disubstituted 4-chromanones, coumarins, and 2-substituted chromones were readily and efficiently assembled, including the naturally occurring coumarins citropten, scoparone, and ayapin. Addition of phenols to biselectrophilic 5-alkylidene Meldrum's acids proceeded through two distinct multibond-forming modes: Friedel-Crafts C-alkylation/(O-acylation and Friedel-Crafts C-acylation/O-alkylation. The regioselectivity of the catalytic annulation reaction was controlled by the degree of substitution on the alkylidene moiety.