5128-44-9

Basic information

• Product Name: 4',7-DIMETHOXY-5-HYDROXYFLAVONE
• Synonyms: 4',7-DIMETHOXY-5-HYDROXYFLAVONE;4',7-DIMETHOXYAPIGENIN;4',7-O-DIMETHYLAPIGENIN;ACACETIN 7-O-METHYL ETHER;APIGENIN-4',7-DI-O-METHYL ETHER;5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4-benzopyrone;apigenin dimethylether;5-Hydroxy-4',7-dimethoxyflavone
• CAS NO: 5128-44-9
• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.29
• EINECS: 225-867-4
• Product Categories: Tri-substituted Flavones
• Mol File: 5128-44-9.mol
• Article Data: 24

Chemical Properties

• Melting Point: 139-140 °C
• Boiling Point: 515.2°C at 760 mmHg
• Flash Point: 193.3°C
• Appearance: /
• Density: 1.321g/cm³
• Vapor Pressure: 3.09E-11mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 6.35±0.40(Predicted)
• CAS DataBase Reference: 4',7-DIMETHOXY-5-HYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4',7-DIMETHOXY-5-HYDROXYFLAVONE(5128-44-9)
• EPA Substance Registry System: 4',7-DIMETHOXY-5-HYDROXYFLAVONE(5128-44-9)

Safety Data

• Hazardous Substances Data: 5128-44-9(Hazardous Substances Data)

Usage

Definition

ChEBI: A dimethoxyflavone that is the 7,4'-dimethyl ether derivative of apigenin.

InChI:InChI=1/C17H14O5/c1-20-11-5-3-10(4-6-11)15-9-14(19)17-13(18)7-12(21-2)8-16(17)22-15/h3-9,18H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 480-44-4 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 
• 437-64-9 genkwanin 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 29424-96-2 naringenin-4',7-dimethyl ether 
• 5631-70-9 4',5,7-trimethoxyflavone 
• 3420-72-2 2'-hydroxy-4,4',6'-trimethoxychalcone 
• 771481-08-4 7-benzyl-3'-phenyltetrazolyldiosmetin 
• 771480-96-7 3'-O-(1-phenyltetrazol-5-yl)diosmin 
• 520-34-3 diosmetin 
• 480-36-4 acacetin 7-O-rutinoside 
• 520-27-4 diosmin 

Downstream Products

• 874005-08-0 8-chloromethyl-5-hydroxy-7-methoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 742097-95-6 6-chloromethyl-5-hydroxy-7-methoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 89456-41-7 5,8-dihydroxy-7-methoxy-2-(4-methoxyphenyl)-4-benzopyrone 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 50848-66-3 7,4'-dimethoxy-5-hydroxy-6-iodoflavone 
• 100-09-4 4-methoxybenzoic acid 
• 5631-70-9 4',5,7-trimethoxyflavone 
• 57096-03-4 5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone 
• 520-18-3 kaempferol 
• 15486-33-6 4',7,-di-O-methylkaempferol 
• 1098-92-6 kaempferol 5,7,4'-trimethyl ether 
• 15486-34-7 5-hydroxy-3,4',7-trimethoxyflavone 
• 16692-52-7 3,4',5,7-tetramethoxyflavone 
• 50848-67-4 6-iodo-5,7,4'-trimethoxyflavone 

Relevant articles and documents

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Syntheses and crystal structures of two apigenin alkylation derivatives

Two apigenin alkylation derivatives, 4′,7-dimethoxyl-5-hydroxyflavone (I) and 4′,7-diethoxyl-5-hydroxyflavone (II), have been synthesized and their crystal structures were determined by 1H NMR and single crystal X-ray diffraction study. (I) is triclinic, space group P-1 with a = 7.120(5) A, b = 7.297(5) A, c = 13.559(10) A, α = 89.313(12)°, β = 86.298(12)°, γ = 83.999(13)° and Z = 2. (II) is monoclinic, space group P 21 /c with a = 16. 309(4) A, b = 7.303(2) A, c = 15.185(4) A, α = 90.00°, β = 115.70(2)°, γ = 90.00° and Z = 4. They have the same flavone skeleton which is composed of a benzopyranone moiety and a phenyl moiety. Molecules of (I) are linked into a two-dimensional network by a combination of C-H...O hydrogen bond and π-π stacking interactions. (II) shows some discrepancies with (I) and the molecules are linked into a column by π-π stacking interaction.

Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity

A library of 33 polymethoxylated flavones (PMF) was evaluated for heme-binding affinity by biomimetic MS assay and in vitro antiplasmodial activity on two strains of P. falciparum. Stability of heme adducts was discussed using the dissociation voltage at 50% (DV50). No correlation was observed between the methoxylation pattern and the antiparasitic activity, either for the 3D7 chloroquine-sensitive or for the W2 chloroquine-resistant P. falciparum strains. However, in each PMF family an increased DV50 was observed for the derivatives methoxylated in position 5. Measurement of intra-erythrocytic hemozoin formation of selected derivatives was performed and hemozoin concentration was inversely correlated with heme-binding affinity. Kaempferol showed no influence on hemozoin formation, reinforcing the hypothesis that this compound may exert in vitro antiplasmodial activity mostly through other pathways. Pentamethoxyquercetin has simultaneously demonstrated a significant biological activity and a strong interaction with heme, suggesting that inhibition of hemozoin formation is totally or partially responsible for its antiparasitic effect.

Synthesis of Benzopyran-Fused Flavone Derivatives via Microwave-Assisted Intramolecular C-H Activation

A microwave-assisted intramolecular direct arylation method for the synthesis of benzopyran-fused flavone derivatives containing natural flavone backbones is described. Different polyalkoxy flavones were synthesized and functionalized with 2-bromobenzyl bromide. The resulting compounds were subjected to palladium-catalyzed intramolecular direct arylation reactions supported by microwave irradiation to produce fused tetracyclic flavones. In the case of the 7-substituted chrysin derivative, the regioselectivity of the coupling was also examined.