4143-74-2

Basic information

• Product Name: 4'-METHOXYFLAVONE
• Synonyms: 4'-METHOXYFLAVONE;METHOXYFLAVONE, 4'-;2-(4-methoxyphenyl)-4-benzopyrone;2-(4-methoxyphenyl)-4h-1-benzopyran-4-on;2-(4-Methoxy-phenyl)-chromen-4-one;4H-1-Benzopyran-4-one,2-(4-methoxyphenyl)-;2-(4-Methoxyphenyl)-4H-1-benzopyran-4-one;2-(4-methoxyphenyl)chromone
• CAS NO: 4143-74-2
• Molecular Formula: C₁₆H₁₂O₃
• Molecular Weight: 252.26
• EINECS: 223-968-8
• Product Categories: Mono-substituted Flavones
• Mol File: 4143-74-2.mol

Chemical Properties

• Melting Point: 157-158°C
• Boiling Point: 401.5 °C at 760 mmHg
• Flash Point: 188.2 °C
• Appearance: white/
• Density: 1.24 g/cm³
• Vapor Pressure: 1.18E-06mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble5mg/mL, clear (warmed)
• CAS DataBase Reference: 4'-METHOXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-METHOXYFLAVONE(4143-74-2)
• EPA Substance Registry System: 4'-METHOXYFLAVONE(4143-74-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 4143-74-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4'-METHOXYFLAVONE is used as a therapeutic agent for its potential benefits in cancer prevention and treatment. It is valued for its ability to reduce inflammation and oxidative stress in the body, which can contribute to the prevention and management of various health conditions.
Used in Nutraceutical Industry:
4'-METHOXYFLAVONE is used as a dietary supplement for its antioxidant properties, supporting overall health and well-being by combating free radicals and promoting a healthy immune response.
Used in Neuroprotective Applications:
4'-METHOXYFLAVONE is used as a neuroprotective agent for its potential to improve cognitive function and protect against neurodegenerative diseases, offering a natural approach to support brain health.
Used in Anti-Inflammatory Applications:
4'-METHOXYFLAVONE is used as an anti-inflammatory agent to reduce inflammation in the body, which can help alleviate symptoms associated with various inflammatory conditions.

InChI:InChI=1/C16H12O3/c1-18-12-8-6-11(7-9-12)16-10-14(17)13-4-2-3-5-15(13)19-16/h2-10H,1H3

Upstream product

• 36685-41-3 (Z)-4'-methoxyaurone 
• 64-17-5 ethanol 
• 151-50-8 potassium cyanide 
• 6953-32-8 2-(4-methoxyphenyl)chroman-4-one oxime 
• 34000-29-8 [E]-3-(p-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 34811-90-0 2-(4'-methoxyphenyl)-4H-chromene 
• 93868-47-4 2'-acetoxy-4-methoxychalcone dibromide 
• 101278-20-0 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one 
• 118-93-4 o-hydroxyacetophenone 
• 100-07-2 4-methoxy-benzoyl chloride 
• 75630-69-2 (Z)-α-bromo-2'-hydroxy-4-methoxychalcone 
• 136003-87-7 1-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-(4-methoxy-phenyl)-propane-1,3-dione 
• 14221-66-0 (+/-)-trans-3-bromo-2-(4-methoxy-phenyl)-chroman-4-one 
• 491-38-3 1-benzopyran-4(4H)-one 

Downstream Products

• 143468-22-8 2-(4-Methoxy-phenyl)-3-nitro-chromen-4-one 
• 187585-43-9 2-(4-methoxy-3-nitrophenyl)-3-nitro-4H-chromen-4-one 
• 6889-78-7 4'-(methoxy)-3-hydroxyflavone 
• 272777-08-9 3'-chlorosulfonyl-4'-methoxyflavone 
• 71993-33-4 3-chloro-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 73910-85-7 3-bromo-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 150107-86-1 3-iodo-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one 
• 134051-32-4 1a,7a-Dihydro-1a-(4-methoxyphenyl)-7H-oxireno<1>benzopyran-7-one 
• 61495-70-3 3-(4-methoxyphenyl)-5-(2-hydroxyphenyl)-isoxazole 
• 82340-45-2 2-(4-Methoxy-phenyl)-chromen-4-one oxime 
• 128814-95-9 7a-(4-Methoxy-phenyl)-1a,7a-dihydro-1H-7-oxa-cyclopropa[b]naphthalen-2-one 
• 88187-09-1 2-acetoxy-3-bromo-4'-methoxyflavan-4-one 

Relevant articles and documents

Experimental and theoretical insights into the photophysical and electrochemical properties of flavone-based hydrazones

A small library of flavone-based hydrazones has been designed, synthesized and characterized. In this context, thirteen flavone hydrazones (3a-3 m) were synthesized by the acid-catalyzed condensation of flavone with 2,4-dinitrophenylhydrazine (2,4-DNPH) and characterized by different spectral techniques (IR, UV–Vis, NMR and mass spectrometry). The electrochemical, photophysical and theoretical investigations of such type of compounds are hitherto unknown. The electrochemical behavior of these hydrazones at a platinum electrode has been analyzed by cyclic voltammetry (CV) and was investigated at 200, 100 and 40 mVs?1 in acetonitrile (CH3CN). These hydrazones showed a quasi-reversible redox reaction. The oxidation–reduction reactive sites of these derivatives were located via geometry optimization using density functional theory (DFT) at the B3LYP/3–21 g in the Guassian-09 level of theory. Moreover, the target compounds exhibited interesting fluorescent properties. Owing to their excellent photophysical and redox results, a detailed structure-property relationship was established to assess the substituents impact and their position on the physicochemical and electronic properties. All the experimental results were in accordance with the computational studies.

Flavone-based hydrazones as new tyrosinase inhibitors: Synthetic imines with emerging biological potential, SAR, molecular docking and drug-likeness studies

Targeting tyrosinase (TYR), a key enzyme responsible for melanogenesis disorders, is a well-known approach utilized for the development of melanogenesis inhibitor. A variety of dermatological disorders and microbial skin infections can cause hyperpigmentation. Hence, exploring new scaffolds for the treatment of melanogenesis disease is an inspiring goal. In this context, a series of varyingly substituted flavone-based hydrazones have been designed, synthesized and characterized successfully. The present study describes the discovery of novel mushroom tyrosinase inhibitors (TIs) for treating hyperpigmentation. In due course, flavone scaffold has been incorporated into the novel chemotypes that exhibit in vitro inhibitory effects against mushroom tyrosinase for the purpose of discovering anti‐melanogenic agents. Biological investigations of prepared analogs herein demonstrated moderate to excellent activity against most of the fungal-bacterial strains and their activity is comparable to those of commercially available antibiotics i.e., Ciprofloxacin and Ketoconazole. Based on in vitro tyrosinase inhibitory assay, some compounds exhibited potent inhibition particularly, 3g (IC50 = 1.40 ± 0.16 μM), 3j (IC50 = 0.95 ± 0.07 μM), 3o (IC50 = 1.13 ± 0.11 μM), and 3q (IC50 = 1.01 ± 0.1 μM) showed best inhibition i.e., 0.7, 0.5, 0.6 and 0.5 folds, respectively, than kojic acid (IC50 = 1.79 ± 0.6 μM). Lineweaver-Burk plots demonstrated that the most potential derivative 3j tyrosinase inhibition proceeds via non-competitive pathway and the Michaelis-Menton constant (Km) value is 0.0265. Molecular modeling was performed for all tested analogs (3a–3q) using a model of mushroom tyrosinase to find crucial binding modes liable for inhibitory activity. The SARs were preliminarily examined, and the docking study revealed that analogs 3j, 3o and 3p had a strong binding association to tyrosinase (2Y9X). Furthermore, a drug-likeness study was employed and confirmed the favorable activity of the new analogs as a new anti-tyrosinase agent.

Robust alkyl-bridged bis(N-heterocyclic carbene)palladium(II) complexes anchored on Merrifield's resin as active catalysts for the selective synthesis of flavones and alkynones

Highly active and efficient propylene-bridged bis(N-heterocyclic carbene)palladium(II) complexes covalently anchored on Merrifield's resin were synthesized and characterized using various physical and spectroscopic techniques. The two anchored Pd(II) complexes consist of the system: Merrifield's resin-linker-bis(NHC)Pd(II), the linkers being benzyl and benzyl-O-(CH2)3 for (Pd-NHC1@M) and (Pd-NHC2@M), respectively. The short linker anchored bis-benzimidazolium ligand precursor (PBBI-1@M) was synthesized via direct carbon–nitrogen alkylation of a propylene-bridged bis(benzimidazole) (PBBI-1) by Merrifield's resin chlorobenzyl group. The longer linker anchored bis-benzimidazolium ligand precursor (PBBI-2@M) was obtained in a two-step reaction involving first alkylation of (PBBI-1) with 3-chloro-1-propanol followed by a nucleophilic substitution at Merrifield's resin chlorobenzyl group. Both supported ligand precursors (PBBI-1@M and PBBI-2@M) reacted with palladium acetate to produce the two heterogeneous catalysts (Pd-NHC1@M) and (Pd-NHC2@M). 13C NMR palladation shift of the benzimidazole N–C–N (C2) carbon was found very similar in both the liquid NMR spectra of the homogeneous complexes and the CP/MASS spectra of the corresponding covalently anchored complexes. The catalytic activity, stability, and the recycling ability of the supported catalysts have been investigated in the carbonylative Sonogashira coupling reactions of aryl iodides with aryl alkynes and alkyl alkynes and also in the cyclocarbonylative Sonogashira coupling reactions of aryl iodides with aryl alkynes via one pot reactions. The longer linker catalyst Pd-NHC2@M demonstrated excellent catalytic activity, stability, and very high recycling ability in the two carbonylative coupling reactions. These systems exhibit the hypothesized thermodynamic stability offered by the chelate effect in addition to the strong sigma donor ability of a bis(NHC) ligand system generating electron-rich palladium centers that favor the oxidative addition step of the aryl halide.

CF3SOCl-promoted intramolecular cyclization of β-diketones: An efficient synthesis of flavones

An efficient intramolecular cyclization reaction of β-diketones containing a phenyl group with an ortho-hydroxyl substituent was achieved. Using CF3SOCl as an additive, the reaction took place under transition-metal-free and mild conditions. A series of flavones were synthesized in moderate to excellent yields.

A novel one-pot synthesis of flavones

In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization

Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.

Design, synthesis and biological evaluation of substituted flavones and aurones as potential anti-influenza agents

We designed a series of substituted flavones and aurones as non-competitive H1N1 neuraminidase (NA) inhibitors and anti-influenza agents. The molecular docking studies showed that the designed flavones and aurones occupied 150-cavity and 430-cavity of H1N1-NA. We then synthesized these compounds and evaluated these for cytotoxicity, reduction in H1N1 virus yield, H1N1-NA inhibition and kinetics of inhibition. The virus yield reduction assay and H1N1-NA inhibition assay demonstrated that the compound 1f (4-methoxyflavone) had the lowest EC50 of 9.36 nM and IC50 of 8.74 μM respectively. Moreover, kinetic studies illustrated that compounds 1f and 2f had non-competitive inhibition mechanism.

Facile synthesis of 6-phenyl-6h-chromeno [4, 3-b] quinoline derivatives using nahso4&at;sio2 re-usable catalyst and their antibacterial activity study correlated by molecular docking studies

Background: Heterocyclic compounds containing heteroatoms (O, N and S) as part of five or six-membered cyclic moieties exhibited various potential applications, such as pharmaceutical drugs, agrochemical products and organic materials. Among many known heterocyclic moieties, quinoline and its derivatives are one of the privileged scaffolds found in many natural products. In general, quinoline derivatives could be prepared by utilizing ortho-substituted anilines and carbonyl compounds containing a reactive α-methylene group of well-known reaction routes like Friedlander synthesis, Niemantowski synthesis and Pfitzinger synthesis. Moreover, polysubstituted quinolones and their derivatives also had shown considerable interest in the fields of organic and pharmaceutical chemistry in recent years. Objectives: The main objective of our research work is towards the design and synthesis of divergent biological-oriented, proactive analogues with potential pharmacological value inspired by the anti-tubercular activity of 2-phenylquinoline analogues. In this study, we have been interested in the design and synthesis of bioactive, 2, 4-diphenyl, 8-arylated quinoline analogues. Methods: 6-phenyl-6h-chromeno [4, 3-b] quinoline derivatives were synthesized from 4-chloro-2phenyl-2H-chromene-3-carbaldehyde and various substituted aromatic anilines as starting materials using sodium bisulfate embedded SiO2 re-usable catalyst. All these fifteen new compound structures confirmed by spectral data1H &13C NMR, Mass, CHN analysis etc. Furthermore, all these new compounds antibacterial activity strains recorded using the paper disc method. The compound molecular structures were designed using molecular docking study by utilizing the crystallographic parameters of S. Areus Murb protein. Results: A series of fifteen new quinoline derivatives synthesized in moderate to good yields using sodium bisulfate embedded SiO2 re-usable catalyst. The molecular structures of these newly synthesized compounds elucidated by the combination of spectral data along with the elemental analysis. These compounds antibacterial activity study have shown moderate to good activity against, Escherichia coli (Gram-negative) and Staphylococcus aureus (gram-positive) organisms. These antibacterial activity results were also a very good correlation with molecular docking studies. Conclusion: In this study, fifteen new quinoline derivatives synthesized and structures confirmed by spectral data. In fact, all the compounds have shown moderate to good antibacterial activity. In general, the compounds containing the electron donor group at R1 position (R1 = OMe) and the acceptor group at R2 positions (R2 = F or Cl) had shown good antibacterial activity. These antibacterial activity results were also a very good correlation with molecular docking studies showing strong binding energies with the highest value being,-12.45 Kcal mol-1 with S. aureus MurB receptor.

Rh-Catalyzed aldehydic C-H alkynylation and annulation

Novel Rh-catalyzed aldehydic C-H bond alkynylation and annulation for the in situ synthesis of chromones and aurones are described. It involves the sequential aldehyde C-H bond alkynylation of salicylaldehyde with in situ generated 1-bromoalkyne from 1,1-

Temperature-Controlled Stereodivergent Synthesis of 2,2′-Biflavanones Promoted by Samarium Diiodide

In this work, the first example of a radical stereodivergent reaction directed towards the stereoselective synthesis of both (R*,R*)- and (R*,S*)-2,2′-biflavanones promoted by samarium diiodide is reported. Control experiments showed that the selectivity of this reaction was exclusively controlled by the temperature. It was possible to generate a variety of 2,2′-biflavanones bearing different substitution patterns at the aromatic ring in good-to-quantitative yields, being both stereoisomers of the desired compounds obtained with total or high control of selectivity. A mechanism that explains both the generation of the corresponding 2,2′-biflavanones and the selectivity is also discussed. The structure and stereochemistry determination of each isomer was unequivocally elucidated by single-crystal X-ray diffraction experiments.