53350-26-8

Basic information

• Product Name: 3',4',5',5,7-PENTAMETHOXYFLAVONE
• Synonyms: 5,7,3',4',5'-PENTAMETHOXYFLAVONE;3',4',5',5,7-PENTAMETHOXYFLAVONE;3',4',5,5',7-PENTAMETHOXYFLAVONE;PENTAMETHOXYFLAVONE, 3',4',5',5,7-;TRICIN 5,7,4'-TRIMETHYL ETHER;3',4',5,5',7-PENTAMETHOXYFLAVONE 97%;PENTAMETHOXYFLAVONE, 3',4',5',5,7-(RG);PROTOPANAXADIOL(P)
• CAS NO: 53350-26-8
• Molecular Formula: C₂₀H₂₀O₇
• Molecular Weight: 372.37
• Product Categories: Penta-substituted Flavones;Inhibitors;Tyrosine Kinase Inhibitors;Aromatics;Heterocycles
• Mol File: 53350-26-8.mol

Chemical Properties

• Melting Point: 198-200°C
• Boiling Point: 554.4 °C at 760 mmHg
• Flash Point: 243.5 °C
• Appearance: Off-White Crystalline Solid
• Density: 1.244g/cm³
• Solubility: Hot Acetone, Warm Ethanol, Methanol
• CAS DataBase Reference: 3',4',5',5,7-PENTAMETHOXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3',4',5',5,7-PENTAMETHOXYFLAVONE(53350-26-8)
• EPA Substance Registry System: 3',4',5',5,7-PENTAMETHOXYFLAVONE(53350-26-8)

Safety Data

• Hazardous Substances Data: 53350-26-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3',4',5',5,7-PENTAMETHOXYFLAVONE is used as a bioactive compound for its potential chemosensitizing effects. It has been found to inhibit ATPase activity, which can enhance the sensitivity of cancer cells to chemotherapy drugs, improving the overall effectiveness of cancer treatment.
Used in Chemical Research:
As a flavonoid, 3',4',5',5,7-PENTAMETHOXYFLAVONE is used as a subject of study in chemical research for its unique properties and potential applications in drug development. Its chemical structure and biological activities make it a valuable compound for further investigation and potential use in the development of new pharmaceuticals.
Used in Nutraceutical Industry:
Due to its natural origin and potential health benefits, 3',4',5',5,7-PENTAMETHOXYFLAVONE may be used as an ingredient in the nutraceutical industry. It could be incorporated into dietary supplements or functional foods for its potential health-promoting properties.

Upstream product

• 18085-94-4 5,7-diacetoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 
• 77-78-1 dimethyl sulfate 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 53350-27-9 (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 18103-42-9 5,7-dihydroxy-3',4',5'-trimethoxyflavone 
• 1719-88-6 3,4,5-trimethoxybenzoic anhydride 
• 392302-43-1 acetic acid 2-[2,3-dibromo-3-(3,4,5-trimethoxy-phenyl)-propionyl]-3,5-dimethoxy-phenyl ester 
• 54987-78-9 2'-acetoxy-3,4,5,4',6'-pentamethoxy-chalcone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 392302-51-1 Acetic acid 2-[(Z)-2-bromo-3-(3,4,5-trimethoxy-phenyl)-acryloyl]-3,5-dimethoxy-phenyl ester 
• 121817-16-1 2-acetyl-3,5-dimethoxyphenyl-3,4,5-trimethoxyphenyl ester 

Downstream Products

• 18103-41-8 5-hydroxy-7-methoxy-2-(3',4',5'-trimethoxyphenyl)-4H-chromen-4-one 
• 190323-49-0 3-hydroxy-5,7-dimethoxy-2–(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 
• 520-31-0 tricetin 
• 118-41-2 Eudesmic acid 

Relevant articles and documents

Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors

The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC50 of 72 ± 2 nM and its 8-C-glucoside orientin with an IC50 of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 ? resolution and quambalarine B at 2.5 ? resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.

Synthesis and Antiproliferative Activity of Natural and Non-Natural Polymethoxychalcones and Polymethoxyflavones

Two series of polymethoxychalcones and polymethoxyflavones, including the natural products 2′-hydroxy-3,4,5,4′,6′-pentamethoxychalcone (8c), 5,6,7,8,3′,4′,5′-heptamethoxyflavone (6), 5,7,3′,4′,5′-pentamethoxyflavone (9c), 3-hydroxy-5,6,7,8,3′,4′,5′-heptam

Preparation method and application of tricetin

The invention belongs to the field of medicine synthesis, and in particular relates to a preparation method and application of tricetin. The method comprises the following steps: performing hydroxy protection to form a compound 3 by using 2,4,6-trihydroxyacetophenone as a starting material, performing an acylation reaction on the compound 3 and 3,4,5-trimethoxybenzoyl chloride to form a compound 4, performing Baker-Venkataranan rearrangement on the compound 4 to form a compound 5, performing cyclization on the compound 5 under catalysis of H2SO4/HOAc to form a compound 6, and finally performing pyridine hydrochloride deprotection on the compound 6 to form the tricetin, wherein in the step of synthesizing the compound 5, when NaOH is selected as a base and pyridine is selected as a solvent,the yield is greatly improved, and the reaction is relatively stable. According to the method provided by the invention, pharmacological activity experiments show that the compound synthesized by themethod has anti-nerve damage activity, so that the compound has better application prospects in treating nerve damage-related diseases.

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.

Use of flavone and flavanone derivatives in preparation of sedative and hypnotic drugs

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

USE OF FLAVONE AND FLAVANONE DERIVATIVES IN PREPARATION OF SEDATIVE AND HYPNOTIC DRUGS

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

Flavonoids with M1 muscarinic acetylcholine receptor binding activity

Muscarinic acetylcholine receptor- Active compounds have potential for the treatment of Alzheimer's disease. In this study, a series of natural and synthetic flavones and flavonols was assayed in vitro for their ability to inhibit radioligand binding at human cloned M1 muscarinic receptors. Several compounds were found to possess competitive binding affinity (K i = 40-110 μM), comparable to that of acetylcholine (Ki = 59 μM). Despite the fact that these compounds lack a positively-charged ammonium group under physiological conditions, molecular modelling studies suggested that they bind to the orthosteric site of the receptor, mainly through non-polar interactions.

Synthesis of novel flavonoid derivatives as potential HIV-integrase inhibitors

Eighteen novel flavonoid derivatives - substituted chalcones and flavones were synthesized and characterized by using NMR, IR, UV/Vis spectroscopy and elemental analysis. The target compounds were achieved by using a sequence of simple and effective reactions starting from phloroglucinol. The initial hydroxyl groups were protected by methylation and in the final flavones the 5-OH group was selectively demethylated by means of AlBr3. 5-methoxy flavones exhibit a strong fluorescence, which was quenched after the removal of the methyl group.

An environmentally benign synthesis of aurones and flavones from 2′-acetoxychalcones using n-tetrabutylammonium tribromide

A wide variety of aurones (3a-f) can be prepared exclusively from 2′-acetoxychalcones (1a-f) in high yields in two steps, by bromination using n-tetrabutylammonium tribromide (TBATB) in the presence of CaCO3 in CH2Cl2-MeOH (5:2) at 0-5°C followed by cyclization of the brominated products 2a-f on treating with 0.2 M ethanolic KOH solution at 0-5°C, respectively. In contrast various flavone derivatives 6a-f can be obtained exclusively from compounds 1a-f in fairly good yields, by brominating with the same reagent in CH2Cl2, followed by dehydrobromination and finally cyclization on treating with 0.1 M NaOMe solution.

Constituents of the Root Bark of Murraya paniculata Collected in Indonesia

A mixture of fatty acid esters (Va) of murrangatin was obtained from the root bark of Murraya paniculata (Rutaceae) collected in Indonesia together with eleven known constituents of chemotaxonomical significance, and their structures were characterized on