21785-09-1

Basic information

• Product Name: 7-METHOXYFLAVANONE
• Synonyms: METHOXYFLAVANONE, 7-;7-HYDROXYFLAVANONE METHYL ETHER;7-METHOXYFLAVANONE;2,3-Dihydro-7-methoxy-2-phenyl-4H-1-benzopyran-4-one;7-Methoxy-4-flavanone
• CAS NO: 21785-09-1
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• Product Categories: Flavanones;Benzopyrans;Building Blocks;Heterocyclic Building Blocks
• Mol File: 21785-09-1.mol

Chemical Properties

• Melting Point: 89-91 °C(lit.)
• Boiling Point: 435℃
• Flash Point: 209℃
• Appearance: /
• Density: 1.199
• Vapor Pressure: 8.75E-08mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: 7-METHOXYFLAVANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHOXYFLAVANONE(21785-09-1)
• EPA Substance Registry System: 7-METHOXYFLAVANONE(21785-09-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 21785-09-1(Hazardous Substances Data)

Usage

Chemical Description

7-methoxyflavanone and 7-hydroxyflavanone are starting materials for the synthesis of 4-triazolylflavans.

InChI:InChI=1/C16H14O3/c1-18-12-7-8-13-14(17)10-15(19-16(13)9-12)11-5-3-2-4-6-11/h2-9,15H,10H2,1H3

Upstream product

• 75-11-6 diiodomethane 
• 39273-61-5 (E)-1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 22218-55-9 (±)-2,4-cis-7-methoxyflavan-4-ol 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 100-52-7 benzaldehyde 
• 52923-29-2 1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 64-17-5 ethanol 
• 108837-17-8 2-hydroxy-4-methoxy-trans(?)-chalcone 
• 22141-31-7 4’-methoxy-2’-hydroxyl-dihydrochalcone 
• 520-29-6 (-)-(S)-sakuranetin 
• 150-19-6 O-methylresorcine 
• 42327-52-6 7-methoxy-chroman-4-one 
• 98-80-6 phenylboronic acid 
• 6279-84-1 β-(m-methoxyphenoxy)propionitrile 

Downstream Products

• 22395-22-8 7-methoxoyflavone 
• 7478-60-6 7-methoxyflavonol 
• 153446-72-1 3-iodo-7-methoxy-2-phenyl-4H-chromen-4-one 
• 124259-88-7 2-(1,5-diphenyl-1H-pyrazol-3-yl)-5-methoxyphenol 
• 1431952-41-8 3-ferrocenylmethylidenyl-7-methoxy-2-phenylchroman-4-one 
• 65428-04-8 4,2′-dihydroxy-4′-methoxydihydrochalcone 
• 55539-24-7 (+)-2,4-trans-7-methoxyflavan-4-ol 
• 32272-23-4 2-(4-hydroxyphenyl)-7-methoxychromen-4-one 
• 1265379-73-4 C₁₈H₁₅N₃O₃S 
• 37884-24-5 C₂₃H₂₁NO₅S 

Relevant articles and documents

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.

Flavanone-based fluorophores with aggregation-induced emission enhancement characteristics for mitochondria-imaging and zebrafish-imaging

Fluorophores with aggregation-induced emission enhancement (AIEE) characteristics applied in bioimaging have attracted more and more attention in recent years. In this work, a series of flavanone compounds with AIEE characteristics was developed and applied to fluorescence imaging of mitochondria and zebrafish. The compounds were readily prepared by the thermal dehydration of chalcone that was obtained by the reaction of o-hydroxyacetophenone and benzaldehyde. Two of these compounds showed significant AIEE characteristics by fluorescence performance experiments, including optical spectra, fluorescence spectra, fluorescence quantum yield (?F), fluorescence lifetime, and scanning electron microscopy (SEM). Compared with traditional organic fluorescent dyes, these compounds have high fluorescence emission and high fluorescence quantum yield in solid or aggregated state, which overcomes the shortcoming of aggregation-caused quenching (ACQ). More importantly, the two compounds exhibited low cytotoxicity and good cytocompatibility in A549 lung cells at the experimental concentration range and they specifically targeted mitochondria, which make it of great potential use in mitochondria labeling. In addition, they were embryonic membrane permeable and had different affinities for different tissues and organs of zebrafish, but mainly distributed in the digestive system, providing a basis for the application of such compounds in bioimaging. These AIEE compounds with superior properties could be of great potential use in mitochondria imaging and other in vivo studies.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

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.

Synthesis and evaluation of neuroprotective selenoflavanones

The physicochemical properties and antioxidant activity of a molecule could be improved by the substitution of an oxygen atom in a molecule with selenium. We synthesized selenoflavanones and flavanones to evaluate their neuroprotective effects. The selenoflavanones showed improved physicochemical properties, suggestive of the ability to pass through the blood-brain barrier (BBB). They showed in vitro antioxidant effects against hydrogen peroxide, and did not result in severe cytotoxicity. Moreover, infarction volumes in a transient ischemia mouse model were significantly reduced by the selenoflavanone treatments.

Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: A highly enantioselective pathway for accessing chiral flavanones

Chromone has been noted to be one of the most challenging substrates in the asymmetric 1,4-addi-tion of α,β-unsaturated carbonyl compounds. By employing the rhodium complex associated with a chiral diene ligand, (R,R)-Ph-bod, the 1,4-addition of a variety of aryl-boronic acids was realized to give high yields of the corresponding flavanones with excellent enantioselectivities (≥97% ee, 99% ee for most substrates). Ring-opening side products, which would lead to erosion of product enantioselectivity, were not observed under the stated reaction conditions.

CuO nanoparticles as an efficient catalyst for the synthesis of flavanones

CuO nanoparticle was found to be an efficient catalyst for the synthesis of flavanones derivatives from the reactions between 2-hydroxyacetophenones and aromatic aldehydes at room temperature. The protocol offers advantages in terms of higher yields, short reaction times, and mild reaction conditions, with reusability of the catalyst. The structures of the synthesized substituted flavanones were confirmed by their Melting point, FT-IR,1 HNMR,13 CNMR and mass spectral analysis.

Mild and efficient one-pot synthesis of diverse flavanone derivatives via an organocatalyzed Mannich-type reaction

A facile ethylenediamine diacetate (EDDA)-catalyzed one-pot synthesis of biologically interesting flavanone derivatives from 2-hydroxyacetophenones, aromatic aldehydes, and aniline via a Mannich-type reaction is described. This synthetic method provides a rapid access to biologically interesting flavanone derivatives. To demonstrate this method, several biologically interesting natural products bearing a flavanone moiety were synthesized as racemates.

Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold

The effect of aryl substitution on various aspects of the interconversion of ortho-hydroxychalcones and flavanones has been studied using multiple spectroscopic techniques. Derivatization of the core scaffold predictably alters the midpoint pH of this equilibration process suggesting its viability for application as a functional colorimetric molecular switch.

Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to heterocyclic acceptors

Flava Flavanone: Asymmetric conjugate additions to chromones and 4-quinolones are reported utilizing a single catalyst system formed in situ from Pd(OCOCF3)2 and (S)-tBuPyOX. Notably, these reactions are performed in wet solvent under ambient atmosphere, and employ readily available arylboronic acids as the nucleophile, thus providing ready access to these asymmetric heterocycles (see scheme).