2150-11-0

Basic information

• Product Name: 7,3',4'-TRIHYDROXYFLAVONE
• Synonyms: 2-(3,4-dihydroxyphenyl)-7-hydroxy-4h-1-benzopyran-4-on;2-(3,4-dihydroxyphenyl)-7-hydroxy-4h-1-benzopyran-4-one;7,3',4'-TRIHYDROXYFLAVONE;3',4',7-TRIHYDROXYFLAVONE;TRIHYDROXYFLAVONE, 7,3',4'-;TRIHYDROXYFLAVONE, 3',4',7-(RG);4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-hydroxy-;2-(3,4-Dihydroxyphenyl)-7-hydroxy-4H-chroMen-4-one
• CAS NO: 2150-11-0
• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.24
• EINECS: 200-258-5
• Product Categories: Tri-substituted Flavones
• Mol File: 2150-11-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 326-327°C
• Boiling Point: 572.8°Cat760mmHg
• Flash Point: 224°C
• Appearance: /
• Density: 1.548g/cm³
• Vapor Pressure: 1.01E-13mmHg at 25°C
• Refractive Index: 1.732
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.01±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 7,3',4'-TRIHYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7,3',4'-TRIHYDROXYFLAVONE(2150-11-0)
• EPA Substance Registry System: 7,3',4'-TRIHYDROXYFLAVONE(2150-11-0)

Safety Data

• Hazardous Substances Data: 2150-11-0(Hazardous Substances Data)

Usage

General Description

7,3',4'-Trihydroxyflavone is a flavonoid compound also known as Fisetin. It's a pigment commonly found in a number of fruits and vegetables such as strawberries, apples, persimmons, grapes, onions, and cucumbers. 7,3',4'-TRIHYDROXYFLAVONE is known for its excellent antioxidant properties and it's considered as a potential agent against cancer, ageing, and neurological diseases because of its anti-inflammatory, anti-tumour, and anti-viral properties. Additionally, according to some research studies, 7,3',4'-Trihydroxyflavone may also exert protective effects on the heart and liver. The compound is still under investigation for its potential therapeutic benefits.

InChI:InChI=1/C15H10O5/c16-9-2-3-10-12(18)7-14(20-15(10)6-9)8-1-4-11(17)13(19)5-8/h1-7,16-17,19H

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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.

Novel flavonoids

Novel flavonoids of formula (I) 1where A and E form together a C—C or C=C bond; R1, R2, R3, and R4 are H, OH, O(CH2)n— aromatic group, n=0-8; O(CH2)n N(CH3)q with n=0-8, q=0-3; O(CH2)n OH with n=1-8; O(CH2)n-halide with n=1-8; O(CH2)n COOH with n=0-8; O(CH2)n COOR′ with n=0-8 and R′ is C1-C8 alkyl or an aromatic group; O(CH2)n CONH R″ with n=0-8 and R″ is C1-C8 alkyl or an aromatic group, and sugars in mono-, di- or trimeric form or analogues thereof, with the proviso that R1 is not H, at least two of R2, R3 and R4 are H, and at most one of R1, R2, R3 and R4 is OH, are useful for the treatment of drug-induced toxicity, doxorubicin-induced cardiotoxicity, free radical mediated diseases, lung diseases, cancer, diabetes mellitus, cardiovascular disease, or arteriosclerosis.

Synthesis of 3-Acyl- and 3-Carbamoylflavones

Routes to 3-acyl-, 3-carboxamido- and polyhydroxylated flavones have been devised by application of isoxazole methodology and Heck-Stille couplings.Reductive ring opening of 3-alkoxyisoxazoles gives β-keto carboxamides in contrast with 3-alkoxy-2-isoxazolines, which give β-hydroxy esters.