6665-72-1

Basic information

• Product Name: 5-HYDROXY-4'-METHOXYFLAVONE
• Synonyms: 5-HYDROXY-4'-METHOXYFLAVONE;5-HYDROXY-2-(4-METHOXYPHENYL)-4H-CHROMEN-4-ONE
• CAS NO: 6665-72-1
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26
• Mol File: 6665-72-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 155-156 °C
• Boiling Point: 456°Cat760mmHg
• Flash Point: 173.4°C
• Appearance: /
• Density: 1.329g/cm³
• Vapor Pressure: 6.18E-09mmHg at 25°C
• Refractive Index: 1.641
• PKA: 6.77±0.40(Predicted)
• CAS DataBase Reference: 5-HYDROXY-4'-METHOXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXY-4'-METHOXYFLAVONE(6665-72-1)
• EPA Substance Registry System: 5-HYDROXY-4'-METHOXYFLAVONE(6665-72-1)

Safety Data

• Hazardous Substances Data: 6665-72-1(Hazardous Substances Data)

Usage

Also known as

Helichrysetin
Naturally occurring flavonoid compound found in various plants, including Helichrysum species

Properties

Potential antioxidant
Anti-inflammatory
Anticancer
Neuroprotective
Therapeutic agent for skin conditions
Chemopreventive agent against certain types of cancer
Potential in the management of metabolic syndrome and diabetes

Specific Health Benefits

Neuroprotective effects
Potential application in the treatment of neurodegenerative diseases
Therapeutic application for skin conditions
Chemopreventive agent against cancer
Potential in the management of metabolic syndrome and diabetes

InChI:InChI=1/C16H12O4/c1-19-11-7-5-10(6-8-11)15-9-13(18)16-12(17)3-2-4-14(16)20-15/h2-9,17H,1H3

Upstream product

• 6665-67-4 5,4'-dihydroxyflavone 
• 77-78-1 dimethyl sulfate 
• 105285-09-4 4,6'-dimethoxy-2'-hydroxychalcone 
• 6697-63-8 5,4'-Dimethoxyflavone 
• 768-60-5 4-methoxyphenylacetylen 
• 78646-28-3 2′-hydroxy-6′-methoxymethoxyacetophenone 
• 794-94-5 p-Methoxybenzoic anhydride 
• 742079-31-8 2-(4-benzyloxy-phenyl)-5-methoxy-chromen-4-one 
• 106848-87-7 4'-hydroxy-5-methoxyflavone 
• 100-07-2 4-methoxy-benzoyl chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 105285-09-4 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 699-83-2 2,6-dihydroxylacetophenone 

Downstream Products

• 872826-17-0 5,8-dihydroxy-2-(4-methoxy-phenyl)-chromen-4-one 

Relevant articles and documents

Unified Approach to (Thio)chromenones via One-Pot Friedel-Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones

A facile synthetic method to chromenones and thiochromenones has been developed using a one-pot Friedel-Crafts acylation of alkynes with suitably substituted benzoyl chlorides. This unified approach to (thio)chromenones is readily applicable to aryl- and alkylalkynes where the stereochemically well-defined β-chlorovinyl ketone intermediates undergo distinctively different cyclization pathways. The ready availability of both starting materials, alkynes and benzoyl chlorides, coupled with the experimental simplicity makes the current synthetic method to (thio)chromenones fast, efficient, and practical.

Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr 3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3′,4′- dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production.

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.