Cas no 2219380-39-7 (4-methyl-2-(propan-2-yl)furan-3-carboxylic acid)

4-Methyl-2-(propan-2-yl)furan-3-carboxylic acid is a furan-based carboxylic acid derivative with potential applications in organic synthesis and pharmaceutical intermediates. Its structure, featuring a methyl group at the 4-position and an isopropyl substituent at the 2-position of the furan ring, contributes to its unique reactivity and steric properties. This compound may serve as a versatile building block for the development of heterocyclic compounds or as a precursor for functionalized furan derivatives. Its carboxylic acid group allows for further derivatization, enabling the formation of esters, amides, or other derivatives. The product is typically characterized by its purity and stability under standard storage conditions, making it suitable for research and industrial applications.
4-methyl-2-(propan-2-yl)furan-3-carboxylic acid structure
2219380-39-7 structure
Product Name:4-methyl-2-(propan-2-yl)furan-3-carboxylic acid
CAS No:2219380-39-7
MF:C9H12O3
MW:168.189783096313
CID:5213433
PubChem ID:136576250
Update Time:2025-05-25

4-methyl-2-(propan-2-yl)furan-3-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 4-methyl-2-(propan-2-yl)furan-3-carboxylic acid
    • Inchi: 1S/C9H12O3/c1-5(2)8-7(9(10)11)6(3)4-12-8/h4-5H,1-3H3,(H,10,11)
    • InChI Key: MAELZIWFXVQDNZ-UHFFFAOYSA-N
    • SMILES: O1C=C(C)C(C(O)=O)=C1C(C)C

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Additional information on 4-methyl-2-(propan-2-yl)furan-3-carboxylic acid

Research Brief on 4-methyl-2-(propan-2-yl)furan-3-carboxylic acid (CAS: 2219380-39-7) in Chemical Biology and Pharmaceutical Applications

4-methyl-2-(propan-2-yl)furan-3-carboxylic acid (CAS: 2219380-39-7) is a furan-based carboxylic acid derivative that has recently garnered attention in chemical biology and pharmaceutical research due to its unique structural features and potential therapeutic applications. This compound, characterized by its furan ring substituted with a methyl group at the 4-position and an isopropyl group at the 2-position, exhibits promising biological activities, including anti-inflammatory, antimicrobial, and anticancer properties. Recent studies have explored its role as a key intermediate in the synthesis of more complex bioactive molecules and its direct interactions with biological targets.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers investigated the mechanistic basis of 4-methyl-2-(propan-2-yl)furan-3-carboxylic acid's anti-inflammatory effects. The study demonstrated that this compound inhibits the NF-κB signaling pathway by directly interacting with the p65 subunit, thereby reducing the production of pro-inflammatory cytokines such as TNF-α and IL-6. Molecular docking simulations revealed that the carboxylic acid moiety forms critical hydrogen bonds with key residues in the p65 protein, while the hydrophobic furan ring contributes to binding affinity through van der Waals interactions.

Another significant development was reported in ACS Chemical Biology, where 4-methyl-2-(propan-2-yl)furan-3-carboxylic acid was identified as a novel inhibitor of bacterial enoyl-ACP reductase (FabI), an essential enzyme in bacterial fatty acid biosynthesis. The compound showed potent activity against drug-resistant strains of Staphylococcus aureus, with an MIC value of 2 μg/mL. Structural-activity relationship (SAR) studies highlighted the importance of the isopropyl group at the 2-position for maintaining antibacterial activity, while modifications to the carboxylic acid group significantly affected potency.

From a synthetic chemistry perspective, recent advances have been made in the efficient production of 4-methyl-2-(propan-2-yl)furan-3-carboxylic acid. A 2024 Nature Communications paper described a biocatalytic approach using engineered Escherichia coli strains expressing heterologous enzymes for the one-pot conversion of biomass-derived substrates into this valuable building block. This green chemistry method achieved a yield of 85% with excellent enantioselectivity, addressing previous challenges in the racemic synthesis of this compound.

In the pharmaceutical development arena, 4-methyl-2-(propan-2-yl)furan-3-carboxylic acid has emerged as a privileged scaffold for drug discovery. Several patent applications filed in 2023-2024 disclose its incorporation into lead compounds targeting G protein-coupled receptors (GPCRs), particularly those involved in metabolic disorders. The compound's balanced lipophilicity (clogP = 2.1) and molecular weight (168.19 g/mol) make it an attractive fragment for medicinal chemistry optimization programs.

Looking forward, the unique properties of 4-methyl-2-(propan-2-yl)furan-3-carboxylic acid position it as a versatile tool in chemical biology and a promising starting point for therapeutic development. Current research efforts are focused on expanding its applications in targeted protein degradation (PROTAC technology) and as a bioisostere for carboxylic acid-containing drugs to improve pharmacokinetic properties. The compound's commercial availability (currently offered by several fine chemical suppliers at >98% purity) facilitates further investigation by the research community.

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