672-89-9

Basic information

• Product Name: 4-Methoxy-6-methyl-2H-pyran-2-one
• Synonyms: 4-METHOXY-6-METHYL-2H-PYRAN-2-ONE;2H-Pyran-2-one, 6-methyl-4-methoxy;4-methoxy-6-methyl-2h-pyran-2-on;4-methoxy-6-methyl-pyran-2-one;Methyltriacetolacton;Methyltriacetolactone;4-Methoxy-6-methyl-2-pyrone
• CAS NO: 672-89-9
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.14
• EINECS: 211-600-9
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Pyrans
• Mol File: 672-89-9.mol
• Article Data: 25

Chemical Properties

• Melting Point: 83-86 °C(lit.)
• Boiling Point: 280.3 °C at 760 mmHg
• Flash Point: 112.6 °C
• Appearance: /Solid
• Density: 1.14g/cm3
• Vapor Pressure: 0.00382mmHg at 25°C
• Refractive Index: 1.492
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility: Poorly soluble in water.
• CAS DataBase Reference: 4-Methoxy-6-methyl-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxy-6-methyl-2H-pyran-2-one(672-89-9)
• EPA Substance Registry System: 4-Methoxy-6-methyl-2H-pyran-2-one(672-89-9)

Safety Data

• WGK Germany: 3
• RTECS: UQ1225500
• Hazardous Substances Data: 672-89-9(Hazardous Substances Data)

Usage

Uses

4-Methoxy-6-methyl-2H-pyran-2-one is used as a model compound to study the assignment of ring proton resonances in 4-methoxy-6-nonyl-2H-pyran-2-one.

InChI:InChI=1/C7H8O3/c1-5-3-6(9-2)4-7(8)10-5/h3-4H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 541-98-0 6-methyl-pyran-2,4-dione 
• 60-29-7 diethyl ether 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 80-48-8 methyl p-toluene sulfonate 
• 670-35-9 3-bromo-4-methoxy-6-methyl-2H-pyran-2-one 
• 5720-05-8 4-methylphenylboronic acid 
• 1679-18-1 4-Chlorophenylboronic acid 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 77-78-1 dimethyl sulfate 
• 4188-63-0 isopropenyl isopropyl ether 
• 926-66-9 2-ethoxyprop-1-ene 
• 520-45-6 Dehydracetic acid 

Downstream Products

• 93006-94-1 6-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxy-2H-pyran-2-one 
• 1360762-55-5 4-methoxy-6-[2-(4-tert-butylphenyl)ethyl]-2H-pyran-2-one 
• 1360762-58-8 4-methoxy-6-[2-(3-(4-tert-butylphenoxy)phenyl)ethyl]-2H-pyran-2-one 
• 194160-43-5 6,6'-(2,4-bis(3,4-dimethoxyphenyl)cyclobutane-1,3-diyl)bis(4-methoxy-2H-pyran-2-one) 
• 3155-51-9 7,8-dihydro-4-methoxy-6-styryl-2H-pyran-2-one 
• 1360762-53-3 6,6'-(1E,1'E)-2,2'-(1,4-phenylene)bis(ethene-2,1-diyl)bis(4-methoxy-2H-pyran-2-one) 
• 1360762-64-6 6,6'-(2,2'-(1,4-phenylene)bis(ethane-2,1-diyl))bis(4-methoxy-2H-pyran-2-one) 
• 15345-83-2 4-methoxy-6-(3-nitrostyryl)-2H-pyran-2-one 
• 1952-41-6 4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one 
• 56070-89-4 6-[2-(3,4-dimethoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one 
• 15345-87-6 4-methoxy-6-(4-phenyl-1,3-butadienyl)-2H-pyran-2-one 
• 2743-14-8 4-methoxy-6-(2-(3,4-dimethoxyphenyl)ethenyl)-2H-pyran-2-one 
• 60427-83-0 4-methoxy-6-(3,4,5-trimethoxyphenethyl)-2H-pyran-2-one 

Relevant articles and documents

An efficient O-methylation of 4-hydroxy-2-pyrones and 4-hydroxycoumarin

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Regioselective functionalization of pyrones: Facile synthesis of 6-styrylpyrones via KHMDS-mediated aldol condensation

Herein, we disclose our efforts directed toward the synthesis of the kavalactone-based natural product penstyrylpyrone and other related 4-OMe-2-pyrones possessing diverse substituents at the 3-, 5-, and 7-positions. Further, a facile approach to access 6-styrylpyrones via the KHMDS-mediated regioselective aldol condensation of 2-pyrones is described with moderate substrate scope and good to high yields (58–80%). The utility of this methodology was exemplified by the stereoselective construction of desmethoxyyangonin, asnipyrone A, and asnipyrone B.

Biomimetic Total Synthesis of Enterocin

The first chemical total synthesis of the highly oxygenated polyketide enterocin has been accomplished. The key step of the synthesis was a late-stage biomimetic reaction cascade involving two intramolecular aldol reactions in which each step proceeded in 52 % yield (averaged) and which established four of the seven stereogenic centers. The pivotal precursor for the cascade reaction was assembled from three readily available building blocks. A chiral dithioacetal with two stereogenic centers originating from L-arabinose represented the core fragment to both ends of which the other building blocks were attached by aldol reactions. The remaining stereogenic center was installed by Davis oxygenation immediately prior to the key step.

Design, syntheses and lipid accumulation inhibitory activities of novel resveratrol mimics

Hispidine was initially discovered from Ficus Hispida for cardiovascular protection. In this paper, hispidine derivatives, which contain a novel resveratrol-like scaffold, have been designed, synthesized, and assayed as agents against lipid accumulations in 3T3-L1 pre-adipocytes. Six hispidine derivatives have the activity of reducing TG in 3T3-L1 adipocytes in dosage-dependent manner. The most active compound can reduce the lipid accumulation up to 78.4% at 10 μM qPCR and Western blotting results demonstrate that the two most active compounds inhibit both lipodenesis and adipogenesis in 3T3-L1 cells through (1) increasing the phosphorylations of AMPK and ACC, promoting SIRT1 expression. These three proteins are key regulators for lipogenesis and energy metabolism. (2) Decreasing the expressions of PPARγ, sREBP-1c, and FABP4, which are pivotal regulators for adipogenesis. Overall, this work proves that hispidine derivatives diminish the lipid accumulation in 3T3-L1 cell line by downregulating lipogenic and adipogenic pathways.