17422-74-1

Basic information

• Product Name: CHROMONE-3-CARBOXALDEHYDE
• Synonyms: 4H-1-Benzopyran-3-carboxaldehyde, 4-oxo-;CHROMONE-3-CARBOXALDEHYDE;BUTTPARK 29\06-40;AURORA KA-4820;AKOS B022468;AKOS BBS-00006952;3-CHROMONECARBALDEHYDE;3-FORMYLCHROMONE
• CAS NO: 17422-74-1
• Molecular Formula: C₁₀H₆O₃
• Molecular Weight: 174.15
• EINECS: 241-451-5
• Product Categories: Chromones
• Mol File: 17422-74-1.mol
• Article Data: 85

Chemical Properties

• Melting Point: 151-153 °C(lit.)
• Boiling Point: 245.11°C (rough estimate)
• Flash Point: 134.7 °C
• Appearance: Orange/Crystalline Powder
• Density: 1.2135 (rough estimate)
• Vapor Pressure: 0.000951mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Refrigerator (+4°C)
• Sensitive: Air Sensitive
• BRN: 472849
• CAS DataBase Reference: CHROMONE-3-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: CHROMONE-3-CARBOXALDEHYDE(17422-74-1)
• EPA Substance Registry System: CHROMONE-3-CARBOXALDEHYDE(17422-74-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 17422-74-1(Hazardous Substances Data)

Usage

Chemical Properties

orange crystalline powder

Uses

3-Formylchromone may be used in the following studies:Preparation of library of novel (E)-3-(2-arylcarbonyl-3-(arylamino)allyl)-4H-chromen-4-ones, by three-component domino reactions with (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones and anilines under catalyst-free conditions.Facile and ecofriendly synthesis of new chromonyl chalcones.Synthesis of 3-(2-hydroxybenzoyl)quinolines and 7H-chromeno[3,2-c]quinolin-7-ones.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 1995, 1973 DOI: 10.1016/S0040-4039(01)96102-7

General Description

Electrospray ionization mass spectrometry (ESI-MS) of protonated 3-formylchromone (3-FC) shows loss of H2 as a major fragmentation route to yield a ketene cation, which on reaction with water forms a protonated carboxylic acid. The invivo salubrious effects of 3-FC against nitrosodiethylamine (NDEA) mediated early hepatocellular carcinogenesis has been investigated. Synthesis and characterization of 3-FC and its derivatives has been reported.

InChI:InChI=1/C10H6O3/c11-5-7-6-13-9-4-2-1-3-8(9)10(7)12/h1-6H

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 17422-79-6 2-(4-oxo-4H-1-benzopyran-3-yl)-1,3-dioxolane 
• 902779-63-9 (E)-N'-((4-oxo-4H-chromen-3-yl)methylene)benzohydrazide 
• 79-36-7 dichloroacethyl chloride 
• 79-30-1 isobutyryl chloride 
• 1871-76-7 diphenylacetic acid chloride 
• 122-59-8 2-phenoxyacetic acid 
• 79-04-9 chloroacetyl chloride 
• 482378-54-1 (RS)-3-(1-hydroxybut-3-en-1-yl)-4H-chromen-4-one 
• 108-95-2 phenol 
• 49619-82-1 3-bromo-4H-chromen-4-one 
• 119072-55-8 tert-butylisonitrile 
• 90-02-8 salicylaldehyde 

Downstream Products

• 84669-00-1 6-(2-Hydroxybenzoyl)-pyrido<2,3-d>pyrimidin-2,4-dion 
• 84669-03-4 1,3-Dimethyl-6-(2-hydroxybenzoyl)-1,2,3,4-tetrahydro-pyrido<2,3-d>pyrimidin-2,4-dion 
• 126400-48-4 3-(3-(p-chlorophenyl)-3-oxo-1-propenyl)-4H-benzopyran-4-one 
• 146618-31-7 4-[4-(2-Hydroxy-benzoyl)-pyrazol-1-yl]-benzoic acid 
• 78831-30-8 4-oxo-1,2,3,4-tetrahydro-6-hydroxy<1>benzopyrano<3,4-b>quinoline 
• 101640-29-3 3-[1-(4-Chloro-phenylamino)-meth-(E)-ylidene]-2-ethoxy-chroman-4-one 
• 57336-17-1 3-[(4-chlorophenylimino)methyl]chromen-4-one 
• 57336-16-0 3-(p-Methoxyphenyliminomethyl)-1-benzopyran-4(4H)-one 
• 138886-51-8 4',5'-bis(2,4,6-trimethylphenyl)-4,4a-dihydrospiro<3H,10H-pyrano<4,3-b><1>benzopyran-3,2'-<1,3>dioxolan>-10-one 
• 138886-51-8 4',5'-bis(2,4,6-trimethylphenyl)-4,4a-dihydrospiro<3H,10H-pyrano<4,3-b><1>benzopyran-3,2'-<1,3>dioxolan>-10-one 
• 138886-49-4 4,4a-dihydro-4',5'-diphenylspiro<3H,10H-pyrano<4,3-b><1>benzopyran-3,2'-<1,3>dioxolan>-10-one 
• 138886-49-4 4,4a-dihydro-4',5'-diphenylspiro<3H,10H-pyrano<4,3-b><1>benzopyran-3,2'-<1,3>dioxolan>-10-one 
• 172276-99-2 (4aR,4'S,5'S)-4',5'-bis(2-methylphenyl)-4,4a-dihydrospiro<3H,10H-pyrano<4,3-b><1>benzopyran-3,2'-<1,3>dioxolan>-10-one 

Relevant articles and documents

Synthesis and reactivity of 3-(1-hydroxy-3-buten-1-yl)chromone

Zn-induced allylation of chromone-3-carbaldehyde 1 produces 3-(1-hydroxy-3-butene-1-yl)chromone 2, which gives back 1 on treatment with formalin under acidic conditions, and reacts differently towards nitrogenous nucleophiles.

Synthesis and structure elucidation of polyphenols containing the N′-methyleneformohydrazide scaffold as aurora kinase inhibitors

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Diels-Alder reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethane. New synthesis of benzo[b]xanthones

An efficient new route to the benzo[b]xanthone system has been developed and applied to the synthesis of several new derivatives. The cycloaddition reactions of chromone-3-carboxaldehydes 12, reacting as dienophiles, with ortho-benzoquinodimethane 7 gave a diastereomeric mixture of cycloadducts 8 and 9. The formation of these compounds results from the Diels-Alder reactions of 12 and 7 followed by the in situ deformylation. The oxidation of adducts 8 and 9 with dimethyl sulfoxide in the presence of iodine gave the novel benzo[b]xanthones 11 in good yields.

Improved selective reduction of 3-formylchromones using basic alumina and 2-propanol

Treatment of formylchromones, dissolved in 2-propanol with basic alumina at 75°C, selectively reduces the formyl group with good yields without any activation process of the alumina.

Microwave-induced protection and deprotection of 4-oxo-(4H)-1-benzopyran-3-carbaldehydes catalysed by Envirocat EPZ10R

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Solid-supported synthetic equivalents of 3-formylchromone and chromone

Treatment of bound o-hydroxyacetophenone 10 under Vilsmeier-Haack reaction conditions yields 11a or 12b, synthetic equivalents of 3-formylchromone (1) and chromone (13) respectively, depending on the resin used as solid support (Merrifield or Wang chloro

Kinetics and mechanism of Vilsmeier-Haack synthesis of 3-formyl chromones derived from O-hydroxy aryl alkyl ketonea : A structure reactivity study

Kinetics of Vilsmeier-Haack reaction with o-hydroxy acetophenones (OHAP) have been investigated in different solvent systems comprising either a single component viz., dichloromethane (DGM), dichloroethane (DCE), acetonitrile (ACN), benzene or binary solvent mixtures of benzene and acetonitrile. The study revealed a total second order kinetics with a first order dependence on each of the [reactant] namely, [VH adduct] and [OHAP]. Increase in the dielectric constant (D) of the medium altered the rate of the reaction non linearly. The data did not fit into either Amis or Kirkwood's theories. These results were interpreted in terms of solvent-solute and solvent-cosolvent interactions. Structure-reactivity correlations have been explained by Hammett's equation.

Biogenic synthesis of ZnO nanoparticles from Parthenium histerophorus extract and its catalytic activity for building bioactive polyhydroquinolines

Abstract: In the present protocol, biogenic synthesis of ZnO nanoparticles using an aqueous extract of weed, i.e. Parthenium is efficiently carried out. The proficient and operationally simple catalytic application of biogenic ZnO nanoparticle is explored towards a synthesis of pharmaceutically relevant and densely functionalized polyhydroquinolines by condensation of four components viz. aromatic aldehyde, dimedone, ethyl acetoacetate, and ammonium acetate. The synthesized polyhydroquinolines were screened for their antimicrobial activity against bacteria and fungi; some of them exhibit better to excellent activity. The developed protocol is enriched with captivating advantages such as excellent yields, shorter reaction time, recyclable catalyst and constructive use of an aqueous extract of Parthenium for the synthesis of ZnO nanoparticle. Graphical abstract: [Figure not available: see fulltext.]

Selective and sensitive colorimetric sensor for CN- in the absence and presence of metal ions (Cu2+/Ni2+): Mimicking logic gate behaviour

Enone based anion sensors have significance due to their colorimetric reaction upon deprotonation and variable occurrence in the conjugated moiety. We have designed a novel and easily forming cromene-isonicotinohydrazide based probe, exhibiting selectivity towards CN- through the naked eye. A Job's plot displays 1:1 stoichiometry along with a 0.76/0.68 μM detection limit. The results accentuate that upon addition of cations (Cu2+/Ni2+) to the heteroatom of donor moiety, sensitivity improves. The limits of detection were found to be 3.5/6.3 μM in the presence of Cu2+/Ni2+. The mechanism was proved by FTIR, NMR, DFT and -OH titration.

Synthesis, in vitro α-glucosidase inhibitory activity and docking studies of novel chromone-isatin derivatives

A novel series of chromone-isatin derivatives 6a–6p were designed, synthesized and characterized by 1H NMR, 13C NMR and HRMS. These novel synthetic compounds were evaluated for inhibitory activity against yeast α-glucosidase enzyme. The results of biological test have shown that all tested compounds exhibited excellent to potent inhibitory activity in the range of IC50 = 3.18 ± 0.12–16.59 ± 0.17 μM as compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Compound 6j (IC50 = 3.18 ± 0.12 μM) with a hydroxyl group at the 7-position of chromone and a 4-bromobenzyl group at the N1-positions of isatin, was found to be the most active compound among the series. Furthermore, molecular docking study was performed to help understand binding interactions of the most active analogs with α-glucosidase enzyme. These results indicated that this class of compounds had potential for the development of anti-diabetic agents.

Design, synthesis and evaluation of novel β-carboline ester analogues as potential anti-leishmanial agents

Leishmaniasis is one of today's most neglected diseases. The emergence of new anti-leishmanial therapies emphasizes several study groups funded by the World Health Organization. The present investigation will focus on the research to determine a few new potential derivatives of β-carboline ester derivatives against leishmaniasis. The in-silico predicted ADMET properties of most of the titled compounds are in an acceptable range and having drug like properties. Among all the tested analogs, compound ES-3 (EC50 3.36 μM; SI > 29.80) showed comparable and equipotent anti-leishmanial activity as that of standard drug miltefosine (EC50 4.80 μM; SI > 20.80) against amastigote forms of the tested L. infantum strain. Two compounds ES-6 and ES-10 exhibited significant activity with EC50 10.16, 13.56 μM; SI > 4.90, 7.37, respectively. In-silico based molecular docking and dynamics study of the significantly active analog also performed to study the putative binding mode, interaction pattern at the active site of the target leishmanial trypanothione reductase enzyme as well as stability of the target-ligand complex. The changes in the conformation of molecules during MD (frame wise trajectory analysis) provided new insights for the development of novel potent molecules. These findings will further give insight that will help modify the compound ES-3 for better potency and the design of novel inhibitors for leishmaniasis. Communicated by Ramaswamy H. Sarma.

Novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors: Design, synthesis, biological evaluation and molecular modelling studies

Here-in, we present molecular design, chemical synthesis and evaluation of novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors. The newly synthesized compounds were evaluated for their in vitro cytotoxicities against A549 (lung cancer), MDA-MB-231 and BT-471 (breast cancer), HepG2 (liver cancer) and HCT-116 (colon cancer) cell lines by MTT assay. Among the synthesized compounds, compound 12b showed excellent anticancer activity on MDA-MB-231 cell line with IC50 value of 0.95 ± 1.88 μM and was verified to be safe in normal human bronchial epithelial cells (Beas-2B). Apoptosis induced by the lead 12b was observed using morphological observations, AO/EB and DAPI staining procedures. Further, dose-dependent increase in the depolarization of mitochondrial membrane was also observed through JC-1 staining. Annexin V-FITC/PI assay confirmed that 12b induced early apoptosis. Additionally, cell cycle analysis indicated that the MDA-MB-231 cells were arrested at sub-G2/M phase and also inhibited tubulin polymerization with IC50 value of 3.54 ± 0.2 μM. Molecular docking simulations were employed to identify the important binding modes responsible for the tubulin inhibitory activity, thus supporting their effective anticancer potential.

Chromone dioxadiazole compound as well as preparation method and application thereof

The preparation method comprises the following steps: adding an intermediate F and bis (acetoxy) iodobenzene to dichloromethane for reaction to obtain the chromone compound. The invention provides a novel chromone dioxadiazole compound and a preparation method thereof, and overcomes the defects of large toxicity and high preparation cost of the traditional method.