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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isocoumarans Phthalides
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isocoumarans Isobenzofuranones Phthalides

4,5-Dimethoxyisobenzofuran-1(3H)-one (CAS No. 4741-58-6): An Overview of Its Structure, Properties, and Applications in Medicinal Chemistry

4,5-Dimethoxyisobenzofuran-1(3H)-one (CAS No. 4741-58-6) is a versatile organic compound that has garnered significant attention in the field of medicinal chemistry due to its unique structural features and potential biological activities. This compound, also known as DMIBF, is a member of the isobenzofuranone family and is characterized by its distinctive methoxy substituents at the 4 and 5 positions. The molecular formula of DMIBF is C₉H₁₀O₄, and it has a molecular weight of 178.17 g/mol.

The chemical structure of DMIBF consists of a six-membered ring fused to a five-membered ring, with two methoxy groups attached to the five-membered ring. This unique arrangement contributes to the compound's stability and reactivity, making it an attractive candidate for various chemical transformations and biological studies. The presence of the methoxy groups also enhances the compound's solubility in polar solvents, which is beneficial for its use in both laboratory and industrial settings.

In recent years, significant research efforts have been directed towards understanding the biological properties of DMIBF. One notable area of interest is its potential as an antioxidant. Studies have shown that DMIBF exhibits strong antioxidant activity, which can be attributed to its ability to scavenge free radicals and inhibit lipid peroxidation. This property makes it a promising candidate for the development of new therapeutic agents aimed at combating oxidative stress-related diseases such as neurodegenerative disorders and cardiovascular diseases.

Beyond its antioxidant properties, DMIBF has also been investigated for its anti-inflammatory effects. In vitro studies have demonstrated that DMIBF can inhibit the production of pro-inflammatory cytokines such as TNF-α and IL-6, which are key mediators of inflammation. These findings suggest that DMIBF could be developed into a novel anti-inflammatory drug for treating conditions like arthritis and inflammatory bowel disease.

The cytotoxicity of DMIBF has also been explored in various cancer cell lines. Research has shown that DMIBF can induce apoptosis in cancer cells by disrupting mitochondrial function and activating caspase pathways. This selective cytotoxicity against cancer cells, while sparing normal cells, highlights its potential as a lead compound for anticancer drug development.

In addition to its direct biological activities, DMIBF has been used as a building block in the synthesis of more complex molecules with enhanced biological properties. For example, researchers have synthesized derivatives of DMIBF by introducing various functional groups at different positions on the molecule. These derivatives have shown improved pharmacological profiles, including increased potency and reduced toxicity, making them attractive candidates for further preclinical and clinical evaluation.

The synthesis of DMIBF can be achieved through several routes, including the cyclization of o-hydroxybenzaldehyde with dimethyl acetylene dicarboxylate (DMAD) followed by hydrolysis and decarboxylation. Another approach involves the reaction of o-hydroxybenzaldehyde with dimethyl carbonate in the presence of a suitable catalyst. These synthetic methods provide chemists with flexible options for producing high-purity DMIBF, which is essential for both research and commercial applications.

The analytical characterization of DMIBF is crucial for ensuring its purity and identity. Common techniques used for this purpose include nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and high-performance liquid chromatography (HPLC). NMR spectroscopy provides detailed information about the molecular structure, while MS confirms the molecular weight and elemental composition. HPLC is used to assess the purity and detect any impurities or degradation products.

In conclusion, 4,5-Dimethoxyisobenzofuran-1(3H)-one (CAS No. 4741-58-6), or DMIBF, is a multifaceted compound with a wide range of potential applications in medicinal chemistry. Its unique structural features, coupled with its diverse biological activities, make it an exciting area of research for scientists and pharmaceutical companies alike. As ongoing studies continue to uncover new insights into the properties and applications of this compound, it is likely that we will see more innovative uses of in the future. p >

• 1567-56-2(1,3-Isobenzofurandione,4,5-dimethoxy-)
• 4087-80-3(4,5,6-Trimethoxy-2-benzofuran-1(3H)-one)
• 67632-32-0(1(3H)-Isobenzofuranone, 5,6,7-trimethoxy-)
• 569-31-3(Meconin)
• 100973-01-1(Diethyl 3,4-dimethoxyphthalate)
• 105518-11-4(1(3H)-Isobenzofuranone, 4,5,7-trimethoxy-)
• 78213-30-6(1(3H)-Isobenzofuranone,6-hydroxy-7-methoxy-)
• 29809-16-3(1(3H)-Isobenzofuranone,7-hydroxy-6-methoxy-)
• 29809-15-2(Meconin-d3)
• 75339-73-0(6,7-dimethoxy-4-methyl-2-benzofuran-1(3H)-one)