62935-72-2

Basic information

• Product Name: 7-Methoxycoumarin-4-acetic acid
• Synonyms: 2-(2-keto-7-methoxy-chromen-4-yl)acetic acid;2-(7-methoxy-2-oxo-4-chromenyl)acetic acid;2-(7-methoxy-2-oxo-chromen-4-yl)acetic acid;2-(7-methoxy-2-oxochromen-4-yl)acetic acid;2-(7-methoxy-2-oxo-chromen-4-yl)ethanoic acid;Mca 2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetic acid;2-(7-Methoxy-2-oxo-2H-chromen-4-yl);(7-Methoxycoumarin-4-yl)acetic acid≥ 95% (NMR)
• CAS NO: 62935-72-2
• Molecular Formula: C₁₂H₁₀O₅
• Molecular Weight: 234.2
• Product Categories: Coumarins;Coumarin;Fluorescent Labels and Indicators;Synthetic Intermediate;Fluorescent Labels & Indicators;Fluorescent Dyes
• Mol File: 62935-72-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 193 °C (dec.)(lit.)
• Boiling Point: 472.9 °C at 760 mmHg
• Flash Point: 87°(189°F)
• Appearance: Off-white powder
• Density: 1.367 g/cm³
• Vapor Pressure: 9.55E-10mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: 2-8°C
• Solubility: Soluble in acetone and dimethyl sulfoxide.
• PKA: 4.22±0.10(Predicted)
• Stability: Moisture, Temperature, Light Sensitive
• CAS DataBase Reference: 7-Methoxycoumarin-4-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Methoxycoumarin-4-acetic acid(62935-72-2)
• EPA Substance Registry System: 7-Methoxycoumarin-4-acetic acid(62935-72-2)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 62935-72-2(Hazardous Substances Data)

Usage

Uses

Used in Fluorescent Reagent Synthesis:
7-Methoxycoumarin-4-acetic acid is used as a precursor for the synthesis of coumarin-type fluorescent reagents. Its role in the production of these reagents is crucial, as it contributes to the development of compounds with enhanced fluorescence properties, which are essential for various analytical techniques.
Used in Chromatographic Detection:
In the field of chromatographic detection, 7-Methoxycoumarin-4-acetic acid is utilized as a key intermediate for the synthesis of fluorescence probes. These probes are vital for the identification and quantification of specific molecules in complex samples, improving the sensitivity and accuracy of the detection process.
Used in Pharmaceutical Research:
7-Methoxycoumarin-4-acetic acid has been employed in the preparation of two novel LysB29 selectively labeled fluorescent derivatives of human insulin. This application highlights its potential in pharmaceutical research, where it can contribute to the development of innovative drugs and therapies.
Used in Peptide Synthesis:
7-Methoxycoumarin-4-acetic acid also serves as a fluorescent label for peptides, which is particularly useful in the synthesis of cell-penetrating peptide transportan 10 (tp10). This application demonstrates its versatility in peptide synthesis, allowing for the creation of molecules with specific properties and functions.

InChI:InChI=1/C12H10O5/c1-16-8-2-3-9-7(4-11(13)14)5-12(15)17-10(9)6-8/h2-3,5-6H,4H2,1H3,(H,13,14)

Upstream product

• 77-92-9 citric acid 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 150-19-6 O-methylresorcine 
• 108-46-3 recorcinol 
• 15991-13-6 7-hydroxycoumarin-4-acetic acid methyl ester 
• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 32632-43-2 ethyl (7-methoxy-2-oxo-2H-chromen-4-yl)acetate 
• 62935-73-3 methyl 2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetate 
• 6950-82-9 2-(7-hydroxy-2-oxochromen-4-yl)acetic acid 
• 77-78-1 dimethyl sulfate 
• 542-05-2 acetonedicarboxylic acid 

Downstream Products

• 62935-73-3 methyl 2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetate 
• 386213-32-7 (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamido)pentanoic acid 
• 1380299-27-3 (3R)-methyl 7-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-5-oxo-8-(3-(trifluoromethyl)phenyl)-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylate 
• 1380299-26-2 (3R)-methyl 7-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-5-oxo-8-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylate 
• 1380299-30-8 (3R)-7-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-5-oxo-8-(3-(trifluoromethyl)phenyl)-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid 
• 1374967-36-8 (3R)-7-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-5-oxo-8-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid 
• 908562-48-1 C₂₁H₂₁NO₇ 
• 812653-62-6 N-[(3-benzoxy-1,6-dimethyl-4-oxo-1,4-dihydropyridin-2-yl)methyl]-2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamide 
• 812653-48-8 N-[2-(3-benzoxy-2-methyl-4-oxopyridin-1(4H)-yl)ethyl]-2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamide 
• 812653-59-1 N-[(3-benzoxy-6-methyl-4-oxo-4H-pyran-2-yl)methyl]-2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamide 

Relevant articles and documents

Antiestrogenic activity and possible mode of action of certain new nonsteroidal coumarin-4-acetamides

The preparation of certain 2-(2-oxo-2H-chromen-4-yl)-N-substituted acetamides IIIa-h was planned as a step in the development of new modified nonsteroidal antiestrogens. The purity of target compounds IIIa-h was checked by thin-layer chromatography (TLC), and their structures were confirmed using various spectroscopic tools including IR, 1H-NMR, 13C-NMR, and MS spectroscopy. Viability tests were applied using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay to evaluate the cytotoxic effect of the synthesized compounds against two breast cancer cell lines, MCF-7 and MDA-MB-231. Compound IIIb proved the most active against MCF-7 cells, with an IC50 value of 0.32 μM. The results of an analysis of in vitro antiestrogenic activity indicated that only compound IIIb exhibited antiestrogenic activity; its IC50 value of 29.49 μM was about twice as potent as that of the reference compound, MIBP. The aromatase activity was evaluated for the synthesized target compounds IIIa-g and the intermediates Ib and IIa. A significant aromatase inhibition was observed for the intermediate Ib and compound IIIe, with IC50 values of 14.5 and 17.4 μM, respectively. Compound IIIb, namely 7-methoxy-4-(2-oxo-2-(piperidin-1-yl)ethyl)-2H-chromen-2-one, could be used as an antiestrogen and/or cytotoxic agent with selective activity against tumor cells.

Synthesis of 2-(2-oxo-2H-chromen-4-yl)acetamides as potent acetylcholinesterase inhibitors and molecular insights into binding interactions

Sixteen novel coumarin-based compounds are reported as potent acetylcholinesterase (AChE) inhibitors. The most active compound in this series, 5a (IC50 0.04 ± 0.01 μM), noncompetitively inhibited AChE with a higher potency than tacrine and gala

Readily functionalizable phosphonium-tagged fluorescent coumarins for enhanced detection of conjugates by mass spectrometry

Fluorescent coumarins are an important class of small-molecule organic fluorophores ubiquitous in different well-established and emerging fields of research including, among others, biochemistry and chemical biology. The present work aims at covering the poor detectability of coumarin-based conjugates by mass spectrometry while keeping important photophysical properties of the coumarin core. In this context, the synthesis of readily functionalizable phosphonium-tagged coumarin derivatives enabling a dual mass-tag and fluorescence labelling of analytes or (bio)molecules of interest through a single-step protocol, is reported. The utility of these coumarins is illustrated through the preparation of fluorogenic substrates that facilitated identification of the peptide fragment released by specific proteolytic cleavages.

Synthetic and Structural Studies on Novel 4,3′-Bicoumarins

A series of directly linked 4-3′ bicoumarins have been synthesized by both Knoevenagel and Perkin reactions. This single-step transformation was accomplished by the reaction of coumarin-4-acetates with substituted salicylaldehydes in presence of piperidin

Facile intramolecular Diels-Alder reaction of 4-(o-propargyloxy) styrylcoumarins leading to highly fluorescent coumarin-containing polycyclic compounds

The 4-(o-propargyloxy)styrylcoumarins are prepared by the condensation of O-propargylated salicylaldehyde with substituted coumarin-4-acetic acids. The intramolecular Diels-Alder reaction of 4-(o-propargyloxy)styrylcoumarins, without any catalyst gives fu

Regiospecific normal Diels-Alder reaction of trans -1,2- biscoumarinylethenes

The reaction of different 7,8-substituted coumarin 4-acetic acids with 7-diethylaminocoumarin-3-carbaldehyde in the presence of piperidine in methanol gives 1,2-biscoumarinylethenes. These compounds undergo regiospecific Diels-Alder reactions at their electron-rich diene components CCCC with electron-deficient dienophiles. The feasibility of normal electron-demand Diels-Alder reactions could be explained on the basis of the HOMO-LUMO gap. All the compounds are new and are intensely colored. Georg Thieme Verlag Stuttgart ? New York.

Modified coumarins. 14. Synthesis of 7-hydroxy-[4,3′]dichromenyl-2, 2′-dione derivatives

New derivatives of 3-(2-oxochromen-4-yl)chromen-2-one, modified analogs of natural dicoumarins, were prepared from substituted coumarin-4-acetic acids.

Design, synthesis, physicochemical properties, and evaluation of novel iron chelators with fluorescent sensors

The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.