6018-41-3

Basic information

• Product Name: Methyl coumalate
• Synonyms: Methyl 2-oxo-2H-pyran-5-carboxylate, Methyl 2-pyrone-5-carboxylate;2-Oxo-2H-pyran-5-carboxylic acid methyl ester;2-Oxopyran-5-carboxylic Acid Acid Methyl Ester;2-Pyrone-5-carboxylic Acid Methyl Ester;Methyl 2-Pyrone-5-carboxylate Coumalic acid methyl ester;2H-Pyran-5-carboxylic acid, 2-oxo-, Methyl ester;Coumalic Acid Methyl Ester 2-Oxopyran-5-carboxylic Acid Methyl Ester Methyl 2-Oxopyran-5-carboxylate 2-Pyrone-5-carboxylic Acid Methyl Ester Methyl 2-Pyrone-5-carboxylate;methyl 6-oxopyran-3-carboxylate
• CAS NO: 6018-41-3
• Molecular Formula: C₇H₆O₄
• Molecular Weight: 154.12
• EINECS: 227-871-1
• Product Categories: Ring Systems;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycles series;Esters
• Mol File: 6018-41-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 65-67 °C(lit.)
• Boiling Point: 178-180 °C60 mm Hg(lit.)
• Flash Point: 178-180°C/60mm
• Appearance: WHITE TO TAN POWDER OR CRYSTALS
• Density: 1.1993 (rough estimate)
• Vapor Pressure: 0.00893mmHg at 25°C
• Refractive Index: 1.4300 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Freely soluble in dichloromethane.
• Merck: 14,2557
• BRN: 126301
• CAS DataBase Reference: Methyl coumalate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl coumalate(6018-41-3)
• EPA Substance Registry System: Methyl coumalate(6018-41-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6018-41-3(Hazardous Substances Data)

Usage

Description

Methyl coumalate, an α, β-unsaturated ketone, is a chemical compound that exhibits cytotoxicity against human normal gingival fibroblast cells and oral squamous cell carcinoma cell line-2. It is a 2-pyrone and acts as a dienophile in Diels-Alder reactions, making it a versatile reagent in various chemical processes.

Uses

Used in Pharmaceutical Industry:
Methyl coumalate is used as a cytotoxic agent for its potential applications in cancer research and treatment, specifically targeting oral squamous cell carcinoma cell line-2.
Used in Chemical Synthesis:
Methyl coumalate is used as a reagent in the Diels-Alder reaction, a widely used method in organic chemistry for the synthesis of various compounds. It reacts with 1,3-butadienes at 100°C to yield tetrahydrocoumarins and 4-methoxycarbonyltricyclo[3.2.1.02,7]octenes, and with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It also undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts.
Used in Organic Chemistry Research:
Methyl coumalate is used as a reagent in phosphine-catalyzed [4+3] annulation of modified allylic carbonates, a reaction that contributes to the development of new synthetic methods and compounds in organic chemistry.
Used in the Preparation of 7-Carboxyquinolizinium Derivatives:
Methyl coumalate is used in the synthesis of 7-carboxyquinolizinium derivatives, which are important intermediates in the preparation of various pharmaceuticals and organic compounds.

InChI:InChI=1/C7H6O4/c1-10-7(9)5-2-3-6(8)11-4-5/h2-4H,1H3

Upstream product

• 67-56-1 methanol 
• 23090-18-8 2-oxo-2H-pyran-5-carbonyl chloride 
• 500-05-0 2H-pyran-2-one-5-carboxylic acid 
• 118481-26-8 methyl 8-methoxy-8-vinyl-3-oxo-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxylate 
• 7664-93-9 sulfuric acid 
• 186581-53-3 diazomethane 
• 617-48-1 malic acid 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 669-40-9 methyl 4-methylcoumalate 
• 59033-40-8 1-(3,4-dimethoxy-phenethyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 
• 872824-55-0 6-oxo-1-phenethyl-1,6-dihydro-pyridine-3-carboxylic acid 
• 64972-00-5 4-anilinomethylene-pentenedioic acid-5-methyl ester 
• 3719-45-7 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 
• 4332-79-0 1-benzyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid 
• 528-44-9 1,2,4-benzene tricarboxylic acid 
• 42933-07-3 methyl 3-bromo-2-oxo-2H-pyran-5-carboxylate 
• 18069-17-5 2-methylglutaric acid 
• 18263-95-1 3,5-dicarboxylic acid-1-benzoic acid methyl ester 
• 75581-72-5 N-phenyl-5-methoxycarbonyl-3,6-endooxycarbonyl-1,2,3,6-tetrahydrophthalimide 
• 75581-80-5 C₂₆H₂₀N₂O₆ 
• 75581-80-5 C₂₆H₂₀N₂O₆ 
• 130232-32-5 4-Methyl-cyclohexa-1,5-diene-1,4-dicarboxylic acid 4-allyl ester 1-methyl ester 

Relevant articles and documents

Diels-Alder reaction of 1-methylcycloprop-2-ene-1-carbonitrile with methyl 2-Oxo-2H-pyran-5-carboxylate

The Diels-Alder reaction of 1-methylcycloprop-2-ene-1-carbonitrile and coumalic acid methyl ester (methyl 2-oxo-2H-pyran-5-carboxylate) gave a 2:1 adduct with endo-syn configuration of both cyclopropane fragments, which was established by X-ray analysis. According to the 1H NMR data, the reaction involves intermediate formation of decarboxylated 1:1 adduct having a cycloheptatriene structure; its isomerization into the corresponding caradiene, followed by addition of the second dienophile molecule, was confirmed by quantum-chemical calculations. Pleiades Publishing, Inc., 2006.

Stereoselective construction of a key hydroindole precursor of epidithiodiketopiperazine (ETP) natural products

An asymmetric synthetic strategy for constructing the divergent-synthesis monomer of epidithiodiketopiperazine (ETP) natural products has been successfully developed. The functionalized 2,3,3a,4,7,7a-hexahydroindole scaffold was constructed by a diastereoselective inverse electron-demand Diels-Alder (IEDDA) reaction. This journal is the Partner Organisations 2014.

Homosecoiridoid alkaloids with amino acid units from the flower buds of lonicera japonica

Nine new homosecoiridoid alkaloids, named lonijaposides O-W (1-9), along with 19 known compounds, were isolated from an aqueous extract of the flower buds of Lonicera japonica. Their structures and absolute configurations were determined by spectroscopic data analysis and chemical methods. Lonijaposides O-W have structural features that involve amino acid units sharing the N atom with a pyridinium (1-5) or nicotinic acid (6-9) moiety. The absolute configurations of the amino acid units were determined by oxidation of each pyridinium ring moiety with potassium ferricyanide, hydrolysis of the oxidation product, and Marfey's analysis of the hydrolysate. This procedure was validated by oxidizing and hydrolyzing synthetic model compounds. The phenylalanine units in compounds 4, 5, and 9 have the d-configuration, and the other amino acid units in 1-3 and 6-8 possess the l-configuration. Compounds 1, 4, 6, and 9 and the known compounds 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, and 5′-O-methyladenosine exhibited antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2) with IC50 values of 3.4-11.6 μM, and 4 inhibited Coxsackie virus B3 replication with an IC50 value of 12.3 μM.