6665-67-4

Basic information

• Product Name: 5,4'-DIHYDROXYFLAVONE
• Synonyms: 4',5-DIHYDROXYFLAVONE;5,4'-DIHYDROXYFLAVONE;5-Hydroxy-2-(4-hydroxyphenyl)-4H-chroMen-4-one;5-Hydroxy-2-(4-hydroxyphenyl)
• CAS NO: 6665-67-4
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• Product Categories: Di-substituted Flavones
• Mol File: 6665-67-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 239-240°C
• Boiling Point: 486oC at 760 mmHg
• Flash Point: 190oC
• Appearance: /
• Density: 1.443g/cm3
• PKA: 6.78±0.40(Predicted)
• CAS DataBase Reference: 5,4'-DIHYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,4'-DIHYDROXYFLAVONE(6665-67-4)
• EPA Substance Registry System: 5,4'-DIHYDROXYFLAVONE(6665-67-4)

Safety Data

• Hazardous Substances Data: 6665-67-4(Hazardous Substances Data)

Usage

General Description

5,4'-dihydroxyflavone is a naturally occurring flavonoid compound found in various plants, including the genus Scutellaria. It has gained attention for its potential therapeutic properties, including anti-inflammatory, neuroprotective, and anti-cancer effects. Studies have shown that 5,4'-dihydroxyflavone has the ability to modulate multiple signaling pathways and target various molecular targets involved in the pathogenesis of diseases such as Alzheimer's, Parkinson's, and cancer. It has been found to exhibit antioxidant properties and has shown promise in improving cognitive function and protecting against neuronal damage. Additionally, 5,4'-dihydroxyflavone has been investigated for its potential to enhance learning and memory, making it a promising candidate for the development of new treatments for neurodegenerative diseases.

Upstream product

• 6697-63-8 5,4'-Dimethoxyflavone 
• 28141-24-4 4-hydroxybenzoyl chloride 
• 699-83-2 2,6-dihydroxylacetophenone 
• 742079-31-8 2-(4-benzyloxy-phenyl)-5-methoxy-chromen-4-one 
• 491-78-1 5-Hydroxyflavone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 105285-08-3 2',6',4-trihydroxychalcone 
• 64687-96-3 5-hydroxy-2-(4-hydroxphenyl)chroman-4-one 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 133642-20-3 4-(tert-butyldimethylsilanyloxy)benzoic acid methyl ester 
• 155721-21-4 5-(2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)isoxazole 
• 141993-06-8 3-(4-hydroxyphenyl)-5-tributylstannylisoxazole 
• 41046-67-7 2-iodoresorcinol 
• 745-39-1 5,4'-diacetoxyflavanone 

Downstream Products

• 121356-07-8 5-hydroxy-2-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-chromen-4-one 

Relevant articles and documents

Microbial metabolism part 9.1 Structure and antioxidant significance of the metabolites of 5,7-dihydroxyflavone (chrysin), and 5- and 6-hydroxyflavones

5,7-Dihydroxyflavone (chrysin) (1) when fermented with fungal cultures, Aspergillus alliaceous (ATCC 10060), Beauveria bassiana (ATCC 13144) and Absidia glauco (ATCC 22752) gave mainly 4′-hydroxychrysin (4), chrysin 7-O-β-D-4-O-methylglucopyranoside (5) and chrysin 7-sulfate (6), respectively. Mucore ramannianus (ATCC 9628), however, transformed chrysin into six metabolites: 4′-hydroxy-3′-methoxychrysin (chrysoeriol) (7), 4′-hydroxychrysin (apigenin) (4) 3′,4′-dihydroxychrysin (luteolin) (8), 3′-methoxychrysin 4′-O-α-D-6- deoxyallopyranoside (9), chrysin 4′-O-α-D-6-deoxyallopyranoside (10), and luteolin 3′-sulfate (11). Cultures of A. alliaceous (ATCC 10060) and B. bassiana (ATCC 13144) metabolized 5-hydroxyflavone (2) into 5,4′-dihydroxyflavone (12) and 4′-hydroxyflavone 5-O-β-D-4-O-methylglucopyranoside (13), respectively. 6-Hydroxyflavone (3) was transformed into 6-hydroxyflavanone (14), flavone 3-O-β-D-4-O- methylglucopyranoside (15) and (±)-flavanone 6-O-β-D-4-O- methylglucopyranoside (16) by cultures of Beauveria bassiana (ATCC 13144). The structures of the metabolic products were elucidated by means of spectroscopic data. The significance of the metabolites as antioxidants in relation to their structure is briefly discussed.

A one-step synthesis of 5-hydroxyflavones

5-hydroxy flavones were prepared in one step starting from 2,6- dihydroxyacetophenone. The latter was treated with an aroyl chloride in the presence of an excess of potassium carbonate to afford 5-hydroxyflavones.

A Short and Facile Synthetic Route to Hydroxylated Flavones. New Syntheses of Apigenin, Tricin, and Luteolin

Reaction of lithium polyanions generated from o-hydroxyacetophenones 3a-f with O-silyloxylated benzoates 2a-d gave 1-aryl-3-(2-hydroxyphenyl)-1,3-propanediones 4a-n, which on treatment with acetic acid containing 0.5percent H2SO4 at 95 - 100 deg C afforded hydroxylated flavones 5-18 in high yields (76 - 92percent).