5631-70-9

Basic information

• Product Name: 4',5,7-TRIMETHOXYFLAVONE
• Synonyms: APIGENIN-4',5,7-TRIMETHYL ETHER;APIGENIN TRIMETHYL ETHER;5,7,4'-TRIMETHOXYFLAVONE;4',5,7-TRIMETHOXYFLAVONE;5,7,4'-trimethylapigenin;4',5,7-Trimethoxyflavone;2-(4-Methoxyphenyl)-5,7-dimethoxy-4H-1-benzopyran-4-one;Trimethylapigenin
• CAS NO: 5631-70-9
• Molecular Formula: C₁₈H₁₆O₅
• Molecular Weight: 312.32
• Product Categories: Tri-substituted Flavones
• Mol File: 5631-70-9.mol
• Article Data: 49

Chemical Properties

• Melting Point: 158-160°C (dec.)
• Boiling Point: 506.5 °C at 760 mmHg
• Flash Point: 225.5 °C
• Appearance: /
• Density: 1.242 g/cm³
• Vapor Pressure: 2.21E-10mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 4',5,7-TRIMETHOXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4',5,7-TRIMETHOXYFLAVONE(5631-70-9)
• EPA Substance Registry System: 4',5,7-TRIMETHOXYFLAVONE(5631-70-9)

Safety Data

• Hazardous Substances Data: 5631-70-9(Hazardous Substances Data)

Usage

Uses

4'',5,7-Trimethoxyflavone is significantly effective at inhibiting proliferation of SNU-16 human gastric cancer cells in a concentration dependent manner.

InChI:InChI=1/C18H16O5/c1-20-12-6-4-11(5-7-12)15-10-14(19)18-16(22-3)8-13(21-2)9-17(18)23-15/h4-10H,1-3H3

Upstream product

• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 77-78-1 dimethyl sulfate 
• 480-44-4 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 
• 3420-72-2 flavokawain A 
• 3420-72-2 2'-hydroxy-4,4',6'-trimethoxychalcone 
• 74-88-4 methyl iodide 
• 66074-95-1 4',5,7-trimethoxyflavanone 
• 76288-41-0 1-(4'-methoxyphenyl)-3-(2''-hydroxy-3'',6''-dimethoxyphenyl)-1,3-propanedione 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 100-07-2 4-methoxy-benzoyl chloride 
• 5128-44-9 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 621-23-8 1,2,3-trimethoxybenzene 
• 94103-36-3 (2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 
• 34446-64-5 (E)-3-(4-methoxyphenyl)propenoyl chloride 

Downstream Products

• 5830-31-9 N,N-dimethyl-3-phenylpropanamide 
• 123-11-5 4-methoxy-benzaldehyde 
• 621-82-9 Cinnamic acid 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 5128-44-9 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 1098-92-6 kaempferol 5,7,4'-trimethyl ether 
• 480-44-4 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 
• 520-18-3 kaempferol 
• 15486-33-6 4',7,-di-O-methylkaempferol 
• 15486-34-7 5-hydroxy-3,4',7-trimethoxyflavone 
• 16692-52-7 3,4',5,7-tetramethoxyflavone 
• 50848-66-3 7,4'-dimethoxy-5-hydroxy-6-iodoflavone 
• 50848-67-4 6-iodo-5,7,4'-trimethoxyflavone 
• 49620-13-5 robustaflavone 

Relevant articles and documents

Size and branching effects on the fluorescence of benzylic dendrimers possessing one apigenin fluorophore at the core

Different generations of dendrimers incorporating one fluorescent core of apigenin and three Fréchet benzylic dendrons have been prepared. The chief geometric features of these dendrimers have been obtained by Molecular Dynamics simulations. These computa

Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer

Poly (ADP-ribose) polymerase-1 (PARP-1) is a potential target for the discovery of chemosensitizers and anticancer drugs. Amentoflavone (AMF) is reported to be a selective PARP-1 inhibitor. Here, structural modifications and trimming of AMF have led to a series of AMF derivatives (9a-h) and apigenin-piperazine/piperidine hybrids (14a-p, 15a-p, 17a-h, and 19a-f), respectively. Among these compounds, 15l exhibited a potent PARP-1 inhibitory effect (IC50 = 14.7 nM) and possessed high selectivity to PARP-1 over PARP-2 (61.2-fold). Molecular dynamics simulation and the cellular thermal shift assay revealed that 15l directly bound to the PARP-1 structure. In in vitro and in vivo studies, 15l showed a potent chemotherapy sensitizing effect against A549 cells and a selective cytotoxic effect toward SK-OV-3 cells through PARP-1 inhibition. 15l·2HCl also displayed good ADME characteristics, pharmacokinetic parameters, and a desirable safety margin. These findings demonstrated that 15l·2HCl may serve as a lead compound for chemosensitizers and the (BRCA-1)-deficient cancer therapy.

Synthesis method of isolicoflavonol

The invention provides a synthesis method of isolicoflavonol, which comprises the following steps: carrying out condensation reaction on 2,4-O-R1(protective group, the same below)-6-hydroxyacetophenone and 4-O-R2(protective group, the same below)-benzaldehyde to generate 2',4'-O-R1-6'-hydroxy-4-O-R2-chalcone; oxidizing the chalcone to generate flavonol; carrying out selective protection on 3-OH ofthe flavonol to obtain 3,5,7-O-R1-4'-O-R2-flavonol; removing the protecting group R2 from the 3,5,7-O-R1-4'-O-R2-flavonol to obtain 3,5,7-O-R1-4'-hydroxyflavonol; carrying out 1,1-dimethylpropargyl reaction on the 4,4'-OH site to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonol; carrying out partial hydrogenation on the alkynyl of the 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonolunder the action of a catalyst to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol and carrying out Claisen rearrangement on the 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol to obtain 3,5,7-O-R1-isolicoflavonol, and removing the protecting group R1 from the 3,5,7-O-R1-isolicoflavonol to obtain the isolicoflavonol.