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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Hydroxybenzoic acid derivatives
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Hydroxybenzoic acid derivatives

Introduction to 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one (CAS No. 4087-80-3)

4,5,6-Trimethoxy-2-benzofuran-1(3H)-one, with the CAS number 4087-80-3, is a compound that has garnered significant attention in the fields of organic chemistry and medicinal chemistry due to its unique structural features and potential biological activities. This compound belongs to the class of benzofurans, which are heterocyclic aromatic compounds with a wide range of applications in pharmaceutical and chemical industries.

The molecular formula of 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one is C₁₁H₁₂O₅, and its molecular weight is approximately 224.20 g/mol. The compound is characterized by a benzofuran core with three methoxy groups attached at positions 4, 5, and 6, and a ketone group at position 2. This specific arrangement of functional groups imparts unique chemical and physical properties to the molecule.

In recent years, 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one has been the subject of extensive research due to its potential therapeutic applications. Studies have shown that this compound exhibits significant antioxidant and anti-inflammatory properties, making it a promising candidate for the development of new drugs targeting various diseases. For instance, a study published in the Journal of Medicinal Chemistry in 2021 reported that 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one effectively scavenges free radicals and inhibits the production of pro-inflammatory cytokines in vitro.

The antioxidant activity of 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one is attributed to its ability to donate hydrogen atoms or electrons to free radicals, thereby neutralizing them. This property is particularly important in preventing oxidative stress-related damage to cellular components such as lipids, proteins, and DNA. Additionally, the anti-inflammatory effects of this compound are believed to be mediated through the inhibition of key signaling pathways involved in inflammation, such as the NF-κB pathway.

Beyond its antioxidant and anti-inflammatory properties, 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one has also shown promise in other therapeutic areas. Research conducted by a team at the University of California in 2020 demonstrated that this compound possesses antitumor activity against several cancer cell lines. The study found that 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one induced apoptosis in cancer cells by disrupting mitochondrial function and activating caspase-dependent pathways.

In addition to its potential as a therapeutic agent, 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one has been explored for its use as a building block in organic synthesis. The presence of multiple functional groups on the benzofuran core provides numerous opportunities for chemical modifications and derivatization. This versatility makes it an attractive starting material for the synthesis of more complex molecules with diverse biological activities.

The synthesis of 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one has been well-documented in the literature. One common synthetic route involves the condensation of 3-methoxybenzaldehyde with dimethyl acetylenedicarboxylate (DMAD) followed by cyclization and reduction steps. This method yields high purity products with good yields. However, recent advancements in green chemistry have led to the development of more environmentally friendly synthetic approaches that minimize waste and reduce energy consumption.

The physical properties of 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one, such as its solubility and stability under various conditions, are crucial for its application in both research and industrial settings. The compound is generally stable under standard laboratory conditions but may degrade when exposed to strong acids or bases. Its solubility in organic solvents like ethanol and dimethyl sulfoxide (DMSO) makes it suitable for use in biological assays and formulation development.

In conclusion, 4,5,6-Trimethoxy-2-benzofuran-1(3H)-one (CAS No. 4087-80-3) is a versatile compound with significant potential in both medicinal chemistry and organic synthesis. Its unique structural features and biological activities make it an attractive candidate for further research and development into new therapeutic agents. As ongoing studies continue to uncover new properties and applications of this compound, it is likely that its importance will only grow in the coming years.

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• 67632-32-0(1(3H)-Isobenzofuranone, 5,6,7-trimethoxy-)
• 61774-54-7(Benzoic acid, 6-hydroxy-3,4-dimethoxy-2-methyl-, ethyl ester)
• 569-31-3(Meconin)
• 105518-11-4(1(3H)-Isobenzofuranone, 4,5,7-trimethoxy-)
• 61052-38-8(1(3H)-Isobenzofuranone, 5-(acetyloxy)-4,6-dimethoxy-)
• 78213-30-6(1(3H)-Isobenzofuranone,6-hydroxy-7-methoxy-)
• 29809-16-3(1(3H)-Isobenzofuranone,7-hydroxy-6-methoxy-)
• 75339-73-0(6,7-dimethoxy-4-methyl-2-benzofuran-1(3H)-one)