6665-81-2

Basic information

• Product Name: 3-HYDROXY-5-METHOXYFLAVONE
• Synonyms: METHOXYFLAVONOL, 5-;5-METHOXYFLAVONOL;3-HYDROXY-5-METHOXYFLAVONE
• CAS NO: 6665-81-2
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26
• Product Categories: Di-substituted Flavones
• Mol File: 6665-81-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 173-176°C
• Boiling Point: 448°C at 760 mmHg
• Flash Point: 170°C
• Appearance: /
• Density: 1.353g/cm³
• Vapor Pressure: 8.27E-09mmHg at 25°C
• Refractive Index: 1.651
• PKA: 8.53±0.20(Predicted)
• CAS DataBase Reference: 3-HYDROXY-5-METHOXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-5-METHOXYFLAVONE(6665-81-2)
• EPA Substance Registry System: 3-HYDROXY-5-METHOXYFLAVONE(6665-81-2)

Safety Data

• Hazardous Substances Data: 6665-81-2(Hazardous Substances Data)

Usage

General Description

3-Hydroxy-5-methoxyflavone is a natural flavonoid compound found in various plant sources, including herbs and fruits. It is known for its antioxidant and anti-inflammatory properties, making it a potential candidate for pharmaceutical and medicinal applications. Research suggests that this compound may have potential therapeutic effects, such as in the treatment of neurodegenerative diseases, cancer, and cardiovascular disorders. Additionally, 3-hydroxy-5-methoxyflavone has been found to possess anti-bacterial and anti-viral activities, further highlighting its potential for use in the development of new drugs and treatments. Overall, this compound holds promise for various health-related applications due to its beneficial properties and potential health benefits.

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

Upstream product

• 40524-67-2 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 100-52-7 benzaldehyde 
• 40524-67-2 2'-Hydroxy-6'-methoxychalcone 

Downstream Products

• 6665-69-6 3,5-dihydroxy-2-phenyl-4H-chromen-4-one 
• 1429665-26-8 4-methoxy-2-(3-methylfuran-2-yl)-2-phenylbenzofuran-3(2H)-one 
• 1429665-25-7 3-(but-2-ynyloxy)-5-methoxy-2-phenyl-4H-chromen-4-one 
• 1242087-44-0 3-Hydroxy-5-methoxyflavone 3-glucuronide 
• 1233689-15-0 3-(allyloxy)-5-methoxy-2-phenyl-4H-chromen-4-one 

Relevant articles and documents

Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone

A novel synthetic method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated that both water and the aerobic atmosphere were necessary to ensure the transformation. The selectivity for flavonol or aurone was originated from solvent-triggered intermediates, which were determined by UV-visible spectra from isolated enimine. The phenol-iminium E-A is dominant in water and the ketoenamine intermediate E-B is prevalent in acetonitrile. In the presence of pyrrolidine and oxygen, E-A leads to flavonol through E-I, a zwitterionic-like phenoloxyl-iminium ion, following the key steps of cyclization and a [2 + 2] oxidation; E-B proceeds through path II, a radical process induced by photolysis of E-B with both pyrrolidine and oxygen, to afford aurone. Preliminary mechanistic studies are reported.

Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication

Herein, we report a synthetic method with improved selectivity for 5-substituted flavonols via the Algar-Flynn-Oyamada reaction (AFO), by using of sodium carbonate/hydrogen peroxide A series of 5-substituted flavonols was obtained with moderate to high yields. The mechanism of the AFO reaction was elucidated. LCMS analysis and in situ 1H NMR analysis indicated that the epoxide was involved in the transformation from chalcone to flavonol and/or aurone under alkaline base/peroxide conditions.