7478-60-6

Basic information

• Product Name: 7-METHOXYFLAVONOL
• Synonyms: 7-METHOXYFLAVONOL;3-HYDROXY-7-METHOXYFLAVONE;METHOXYFLAVONOL, 7-;7-Methoxy-3-hydroxy flavone;METHOXYFLAVONOL, 7-(P);METHOXYFLAVONOL, 7-(RG);3-Hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one
• CAS NO: 7478-60-6
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26
• Product Categories: Di-substituted Flavones;Benzopyrans;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 7478-60-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 177-178°C
• Boiling Point: 446.6°C at 760 mmHg
• Flash Point: 169.4°C
• Appearance: /
• Density: 1.353g/cm³
• Vapor Pressure: 9.3E-09mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: 7-METHOXYFLAVONOL(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHOXYFLAVONOL(7478-60-6)
• EPA Substance Registry System: 7-METHOXYFLAVONOL(7478-60-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 7478-60-6(Hazardous Substances Data)

Usage

Uses

7-Methoxyflavonol (cas# 7478-60-6) is a flavenoid which, as a class of compounds, have broad pharmacological activity, including binding to biomolecules such as enzymes, hormone carriers, and DNA, chelating transition metal ions, catalyzing electron transport, and scavenging free radicals.

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

Upstream product

• 52752-67-7 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione 
• 60965-23-3 1-(ω-chloroacetyl)-2-hydroxy-4-methoxybenzene 
• 100-52-7 benzaldehyde 
• 52923-29-2 1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 150-19-6 O-methylresorcine 
• 1371569-96-8 C₁₉H₁₇NO₅ 
• 21785-09-1 7-methoxyflavanone 
• 492-00-2 3,7-dihydroxyflavone 
• 74-88-4 methyl iodide 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 663619-16-7 ethyl 2-(4-methoxy-2-hydroxyphenyl)-2-oxoethanoate 
• 4539-23-5 3-acetoxy-7-methoxy-2-phenyl-chroman-4-one 
• 34000-29-8 [E]-3-(p-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 

Downstream Products

• 2047-54-3 3-hydroxy-2,3,7-trimethoxy-2-phenyl-chroman-4-one 
• 2237-36-7 4-methoxysalicylic acid 
• 21829-43-6 3-acetyl-3,5,4'-trihydroxy-7-methoxyflavone 
• 77184-82-8 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanedione 
• 88214-61-3 7-methoxy-3-(cis-4'-methoxyflavan-4β-yloxy)flavone 
• 20950-52-1 3,7-dimethoxy-2-(3',4'-methylenedioxy-phenyl)chromen-4-one 
• 65-85-0 benzoic acid 
• 1242087-48-4 3-Hydroxy-7-methoxyflavone 3-glucuronide 
• 1233689-17-2 3-(allyloxy)-7-methoxy-2-phenyl-4H-chromen-4-one 
• 157077-00-4 Co(C₂H₄(NCHC₆H₄O)2)(C₉H₃O₃(OCH₃)C₆H₅) 
• 112222-91-0 rhamnocitrin 3-sulphate 

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.

Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis

Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.

2-substituted benzopyran-4-one compounds and application thereof

The invention relates to the technical field of medicine and discloses 2-substituted benzopyran-4-one compounds with a structure shown in general formula I and an application of the compounds in preparation of antifungal drugs and synergistic antifungal drugs. The compounds can be jointly used with azole antifungal drugs, can improve sensibility of drug-resistance bacteria to the azole drugs, reverses drug resistance and produces a synergistic antifungal function.