19852-25-6

Basic information

• Product Name: 5,3',4'-TRIHYDROXYFLAVONE
• Synonyms: 5,3',4'-TRIHYDROXYFLAVONE;4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5-hydroxy-;2-(3,4-Dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one
• CAS NO: 19852-25-6
• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.24
• Product Categories: Tri-substituted Flavones
• Mol File: 19852-25-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 544.4 °C at 760 mmHg
• Flash Point: 212.6 °C
• Appearance: /
• Density: 1.548 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly)
• CAS DataBase Reference: 5,3',4'-TRIHYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,3',4'-TRIHYDROXYFLAVONE(19852-25-6)
• EPA Substance Registry System: 5,3',4'-TRIHYDROXYFLAVONE(19852-25-6)

Safety Data

• Hazardous Substances Data: 19852-25-6(Hazardous Substances Data)

Usage

Description

5,3',4'-Trihydroxyflavone, commonly known as luteolin, is a naturally occurring flavonoid compound found in a variety of plant sources such as fruits, vegetables, and medicinal herbs. It is characterized by its yellow crystalline solid form and possesses a range of biological activities including antioxidant, anti-inflammatory, and anticancer properties. 5,3',4'-TRIHYDROXYFLAVONE has garnered significant interest due to its potential to inhibit cancer cell proliferation, induce apoptosis, and suppress tumor growth, along with its neuroprotective and anti-inflammatory effects, positioning it as a promising candidate for pharmaceutical development for a spectrum of diseases and conditions. Moreover, 5,3',4'-Trihydroxyflavone has demonstrated antimicrobial and antiviral capabilities, broadening its potential therapeutic applications.

Uses

Used in Pharmaceutical Development:
5,3',4'-Trihydroxyflavone is used as a key component in the development of new pharmaceuticals for the treatment of various diseases and conditions due to its diverse biological activities, including its antioxidant, anti-inflammatory, and anticancer properties.
Used in Cancer Therapy:
In the field of oncology, 5,3',4'-Trihydroxyflavone is utilized as a therapeutic agent for its potential to inhibit cancer cell proliferation, induce apoptosis, and suppress tumor growth, making it a valuable asset in the fight against cancer.
Used in Neuroprotection:
5,3',4'-Trihydroxyflavone is used as a neuroprotective agent for its potential to protect the nervous system and mitigate neurodegenerative conditions, given its demonstrated neuroprotective effects.
Used in Anti-Inflammatory Applications:
5,3',4'-TRIHYDROXYFLAVONE is employed as an anti-inflammatory agent, leveraging its ability to reduce inflammation and alleviate symptoms associated with inflammatory diseases.
Used in Antimicrobial and Antiviral Therapies:
5,3',4'-Trihydroxyflavone is used in antimicrobial and antiviral therapies, capitalizing on its demonstrated activities against certain microbes and viruses, thereby contributing to the treatment and prevention of infectious diseases.
Used in the Food Industry:
While not explicitly mentioned in the provided materials, given its presence in various fruits and vegetables, 5,3',4'-Trihydroxyflavone could also be utilized in the food industry for its potential health benefits and as a natural antioxidant to extend the shelf life of products.

Upstream product

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• 93878-59-2 (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-6-methoxyphenyl)prop-2-en-1-one 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 169693-90-7 3-<3,4-di(tert-butyldimethylsilyloxy)phenyl>-5-(2,6-dihydroxyphenyl)isoxazole 
• 41046-67-7 2-iodoresorcinol 
• 169693-94-1 3-(3,4-dihydroxyphenyl)-5-(2,6-dihydroxyphenyl)isoxazole 
• 136198-18-0 5-methoxy-2-(3,4-dimethoxyphenyl)-4H-chromen-4-one 

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 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.