672-89-9

Usage

Uses

Used in Chemical Research:
4-Methoxy-6-methyl-2H-pyran-2-one is used as a model compound for studying the assignment of ring proton resonances in 4-methoxy-6-nonyl-2H-pyran-2-one. This application is crucial for understanding the structure and properties of related compounds, which can be valuable in the development of new materials and pharmaceuticals.
Used in Pharmaceutical Development:
Although not explicitly mentioned in the provided materials, 4-Methoxy-6-methyl-2H-pyran-2-one and its derivatives may have potential applications in the pharmaceutical industry. Their unique chemical structures could be harnessed for the development of new drugs with specific therapeutic effects, such as antimicrobial, antiviral, or anticancer properties.
Used in Material Science:
4-Methoxy-6-methyl-2H-pyran-2-one's heterocyclic structure and functional groups may also make it a candidate for use in material science. It could potentially be incorporated into the design of new materials with specific properties, such as improved stability, reactivity, or selectivity in chemical processes.
Used in Flavor and Fragrance Industry:
Given its molecular structure, 4-Methoxy-6-methyl-2H-pyran-2-one may have potential applications in the flavor and fragrance industry. Its unique chemical properties could contribute to the development of new scents or tastes, enhancing the sensory experience of various products.

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 
• 77-78-1 dimethyl sulfate 
• 6814-64-8 methylenedimethyl sulfurane 
• 52911-90-7 2,4-dimethoxy-6-methylpyrylium fluorosulphonate 
• 104-88-1 4-chlorobenzaldehyde 
• 93338-97-7 5-bromo-4-methoxy-6-methyl-2-pyrone 
• 67-64-1 acetone 
• 80-48-8 methyl p-toluene sulfonate 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 4225-42-7 2-methoxy-6-methyl-pyran-4-one 

Downstream Products

• 52911-98-5 4-Methoxy-6-methyl-2-thiopyron 
• 670-35-9 3-bromo-4-methoxy-6-methyl-2H-pyran-2-one 
• 60427-94-3 6<(2-Pyridyl)vinyl>-4-methoxy-α-pyron 
• 71602-62-5 4-(2-methoxycarbonyl-3,5-dimethoxybenzyl)-6-methyl-2H-pyran-2-one 
• 92591-60-1 methyl 2,4-dimethoxy-5,7-dimethyl-1-naphthoate 
• 84016-84-2 4-methoxy-6-methyl-2-pyrone-3-carboxaldehyde 
• 158205-36-8 6-Methyl-4-oxo-4H-pyran-3-carboxylic acid 
• 35122-84-0 3-Methoxy-5-methyl-N,N-dimethylanilin 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 92120-54-2 2-(2,4-dimethoxy-6-methylphenyl)-6-methyl-4H-pyran-4-one 
• 92591-61-2 4-(2-ethoxycarbonyl-3,5-dimethoxybenzyl)-6-methyl-2H-pyran-2-one 
• 133201-59-9 (1S,6R,7R)-7-Ethoxy-6-methoxy-4-methyl-3-oxa-bicyclo[4.2.0]oct-4-en-2-one 
• 133201-59-9 (1S,6R,7S)-7-Ethoxy-6-methoxy-4-methyl-3-oxa-bicyclo[4.2.0]oct-4-en-2-one 
• 35598-05-1 methyl 4-methoxy-2-methylbenzoate 

Relevant academic research and scientific papers

Synthesis, antitumor activity, and mechanism of action of 6-acrylic phenethyl ester-2-pyranone derivatives

Based on the scaffolds of caffeic acid phenethyl ester (CAPE) as well as bioactive lactone-containing compounds, 6-acrylic phenethyl ester-2-pyranone derivatives were synthesized and evaluated against five tumor cell lines (HeLa, C6, MCF-7, A549, and HSC-2). Most of the new derivatives exhibited moderate to potent cytotoxic activity. Moreover, HeLa cell lines showed higher sensitivity to these compounds. In particular, compound 5o showed potent cytotoxic activity (IC50 = 0.50-3.45 μM) against the five cell lines. Further investigation on the mechanism of action showed that 5o induced apoptosis, arrested the cell cycle at G2/M phases in HeLa cells, and inhibited migration through disruption of the actin cytoskeleton. In addition, ADMET properties were also calculated in silico, and compound 5o showed good ADMET properties with good absorption, low hepatotoxicity, and good solubility, and thus, could easily be bound to carrier proteins, without inhibition of CYP2D6. A structure-activity relationship (SAR) analysis indicated that compounds with ortho-substitution on the benzene ring exhibited obviously increased cytotoxic potency. This study indicated that compound 5o is a promising compound as an antitumor agent.

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.

Linderapyrone: A Wnt signal inhibitor isolated from Lindera umbellata

Linderapyrone, a Wnt signal inhibitor was isolated from the methanolic extract of the stems and twigs of Lindera umbellata together with epi-(-)-linderol A. Linderapyrone inhibited TCF/β-catenin transcriptional activity that was evaluated using cell-based TOPFlash luciferase assay system. To evaluate the structure-activity relationship and mechanism, we synthesized linderapyrone and its derivatives from piperitone. As the results of further bioassay for synthesized compounds, we found both of pyrone and monoterpene moieties were necessary for inhibitory effect. cDNA microarray analysis in a linderapyrone derivative treated human colorectal cancer cells showed that this compound downregulates Wnt signaling pathway. Moreover, we successes to synthesize the derivative of linderapyrone that has stronger inhibitory effect than linderapyrone and ICG-001 (positive control).

Hispidine compound and application thereof

The invention relates to the technical field of synthetic medicine, in particular to a hispidine compound and pharmaceutical salt thereof, and application to the aspect of treating and preventing obesity and hyperlipemia. The hispidine compound can obviously inhibit the accumulation of triglyceride and total fat in the 3T3-L1 preadipocyte differentiation process; the inhibition effect is superiorto that of a positive control compound of jamaicin; no obvious cytotoxicity exists. In addition, a beta-lactam hispidine compound can also regulate and control the phosphorylation of transcription factors AMPK and ACC of fat metabolism and the SIRT1 expression quantity, and can regulate and control the expression quantity of transcription factors PPAR-gamma, SREBP-1c and FABP4 of the adipocyte differentiation. Therefore the medicine containing the hispidine compound and/or the pharmaceutical salt has good effects of inhibiting the adipocyte differentiation and reducing oil drops and triglyceride in the adipocyte; good development prospects are realized in the aspects of treating or preventing obesity and reducing the blood fat.

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.

A caffeic acid phenyl ester compound and its preparation method and application

The invention discloses caffeic acid phenethyl ester compounds. The compounds have a structure shown in the chemical general formula A or B, wherein R1 in the formula A is substituent group on one or more benzene ring; R1 is independently selected from H, alkyl, alkoxy, halogen, nitryl, phenyl or trimethyl halide; R2 in the formula B is independently selected from the following groups shown in the specification. The compounds disclosed by the invention have better inhibiting function for the proliferation of a plurality of human tumor cells, and the compounds can be used for preparing anti-tumor drugs; therefore, the compounds have very high medical value and wide market prospect. (The formulae A and B are shown in the specification).

Synthesis of novel 5,6-dehydrokawain analogs as osteogenic inducers and their action mechanisms

An imbalance between bone resorption by osteoclasts and bone formation by osteoblasts can cause bone loss and bone-related disease. In a previous search for natural products that increase osteogenic activity, we found that 5,6-dehydrokawain (1) from Alpinia zerumbet promotes osteoblastogenesis. In this study, we synthesized and evaluated series of 5,6-dehydrokawain analogs. Our structure-activity relationships revealed that alkylation of para or meta position of aromatic ring of 1 promote osteogenic activity. Among the potential analogs we synthesized, (E)-6-(4-Ethylstyryl)-4-methoxy-2H-pyran-2-one (14) and (E)-6-(4-Butylstyryl)-4-methoxy-2H-pyran-2-one (21) both significantly up-regulated Runx2 and Osterix mRNA expression at 10?μM. These osteogenic activities could be mediated by bone morphogenetic protein (BMP) and activation of p38 MAPK signaling pathways. Compounds 14 and 21 also inhibited RANKL-induced osteoclast differentiation of RAW264 cells. These results indicated that novel 5,6-dehydrokawain analogs not only increase osteogenic activity but also inhibit osteoclast differentiation, and could be potential lead compounds for the development of anti-osteoporosis agents.

Easy and green synthesis of 6-(arylvinyl)-4-hydroxy-3-(phenylsulfanyl)-2H-pyran-2-ones in aqueous potassium hydroxide

A convenient green procedure have been proposed for the synthesis of 6-(2-arylvinyl)-4-hydroxy-3-(phenylsulfanyl)-2H-pyran-2-ones by condensation of 6-(arylvinyl)-4-hydroxy-2H-pyran-2-ones with S-phenyl benzenesulfonothioate in aqueous potassium hydroxide at room temperature.

Potassium fluoride-barium oxide catalysis in an easy and efficient synthesis of methysticin from piperonal under microwave irradiation

Condensation of compounds containing active methylene group with aromatic aldehyde (piperonal) in the presence of BaO on KF without a solvent under microwave irradiation is an efficient synthetic approach to methysticin and derivatives of kavalactones (4-methoxy-6-styryl-pyran-2-ones).