4-Methylesculetin

• CAS: 529-84-0
• Catalog Number: ACM529840-1
• Category: Main Products
• Molecular Weight: 192.17
• Molecular Formula: C10H8O4
• Synonyms: 4-Methylesculetin; 6,7-dihydroxy-4-methylchromen-2-one; 6,7-Dihydroxy-4-methylcoumarin; 6,7-Dihydroxy-4-methyl-2H-chromen-2-one
• IUPAC Name: 6,7-dihydroxy-4-methylchromen-2-one
• SMILES: CC1=CC(=O)OC2=CC(=C(C=C12)O)O
• InChI Key: KVOJTUXGYQVLAJ-UHFFFAOYSA-N
• Boiling Point: 455.5ºC at 760 mmHg
• Melting Point: 274-276ºC
• Flash Point: 190.7ºC
• Density: 1.456 g/cm³
• Appearance: Yellow needle crystal
• EC Number: 208-470-0
• Exact Mass: 192.04200
• Hazard Statements: Xi: Irritant
• Safety Description: S24/25
• WGK Germany: 2

Case Study

4-Methylesculetin for Amelioration of DSS-Induced Intestinal Inflammation

Witaicenis A, et al. Chemico-Biological Interactions, 2018, 280, 59-63.

4-Methylesculetin was experimentally evaluated for its intestinal anti-inflammatory efficacy using a dextran sulfate sodium (DSS)-induced colitis model in mice. Mice were administered 5% DSS in drinking water for 5 days, followed by 2 days of water. Concurrently, 4-methylesculetin was orally administered at doses of 5 or 25 mg/kg daily from day one. Comprehensive assessments, including macroscopic evaluation, histopathology, and biochemical markers, were conducted. Treatment with 25 mg/kg 4-methylesculetin significantly ameliorated colonic inflammation, reduced myeloperoxidase (MPO) activity, and lowered interleukin-6 (IL-6) levels. Additionally, it counteracted glutathione (GSH) depletion, indicating restored antioxidant capacity. The experimental outcomes demonstrated that 4-methylesculetin exerts intestinal protective effects via combined antioxidant and anti-inflammatory mechanisms, highlighting its potential as a therapeutic candidate for inflammatory bowel diseases (IBD).

4-Methylesculetin for Alleviating Peripheral Inflammatory Pain via Sp1-TRPV1 Pathway Inhibition

Zhao W, et al. International Immunopharmacology, 2025, 152, 114379.

In this study, 4-Methylesculetin (4-ME), a coumarin derivative, was experimentally evaluated for its analgesic effects in peripheral inflammatory pain models. Acute and chronic pain were induced in rats via formalin and Complete Freund's Adjuvant (CFA) injections, respectively. Mechanical allodynia and thermal hyperalgesia were quantified using Von Frey filaments and thermal radiation assays. Intraperitoneal administration of 4-ME effectively reduced pain behaviors and inflammatory cytokines (IL-6, TNF-α, IL-1β) in dorsal root ganglia (DRG). Molecular analysis through RT-qPCR, western blotting, and immunofluorescence revealed that 4-ME suppressed the ERK, NF-κB, and NLRP3 pathways, alongside downregulating TRPV1 expression via inhibition of the Sp1 transcription factor. Notably, patch-clamp recordings confirmed that TRPV1 channel function remained unaltered, indicating a transcriptional regulation mechanism. These findings position 4-ME as a promising analgesic candidate targeting the Sp1-TRPV1 axis for inflammatory pain management.

Anti-Inflammatory Mechanisms of 4-Methylesculetin in TNBS-Induced Colitis: Comparative Experimental Study

Witaicenis A, et al. Chemico-Biological Interactions, 2012, 195, 76-85.

4-Methylesculetin was evaluated for its anti-inflammatory efficacy in a TNBS-induced colitis model in rats, with comparison to prednisolone and sulphasalazine. Colitis was chemically induced via intrarectal instillation of trinitrobenzenesulphonic acid (TNBS). The treatment groups received 4-methylesculetin orally, followed by macroscopic scoring and histopathological examination of colon tissues. Biochemical assays quantified glutathione (GSH), myeloperoxidase (MPO), alkaline phosphatase (AP), malondialdehyde (MDA), and metalloproteinase 9 (MMP-9) activity. In vitro, RAW264.7 macrophages, splenocytes, and Caco-2 cells were used to assess cytokine suppression (IL-1β, IL-8, IL-2, IFN-γ) following 4-methylesculetin treatment. The compound significantly preserved mucosal architecture, reduced apoptosis, and inhibited inflammatory enzyme and cytokine levels. These findings underscore 4-methylesculetin's potent intestinal anti-inflammatory effects via oxidative stress modulation and immunosuppressive cytokine regulation.

4-Methylesculetin for Alleviating Aflatoxin B1-Induced Myotoxicity in Grass Carp Muscle Development

He X, et al. Animal Nutrition, 2024, 19, 339-354.

4-Methylesculetin (4-ME) was evaluated for its protective role against aflatoxin B1 (AFB1)-induced myotoxicity in Ctenopharyngodon idella. In a 60-day in vivo study, grass carp were fed diets containing AFB1 (60 μg/kg), 4-ME (10 mg/kg), or both. Parallel in vitro assays utilized primary myoblasts treated with AFB1 (15 μmol/L) and/or 4-ME (0.5 μmol/L). AFB1 impaired muscle growth by suppressing MyoG, MyoD, and MYHC expression, disrupting ECM integrity, and activating the p38 MAPK/uPA/MMP cascade. Co-treatment with 4-ME significantly restored muscle integrity, suggesting that dietary 4-ME mitigates AFB1 toxicity via inhibition of the p38 MAPK pathway and ECM degradation, offering a promising feed additive strategy.

4-Methylesculetin for the Alleviation of Aflatoxin B1-Induced Hepatic Ferroptosis via AMPK-TOR-Ulk1 Axis Modulation

He X, et al. Animal Nutrition, 2025.

In this in vivo study, 4-methylesculetin (4-ME) was experimentally administered to assess its hepatoprotective effects against aflatoxin B1 (AFB1)-induced injury in grass carp (Ctenopharyngodon idella). Juvenile fish (~11.40 g) were divided into four treatment groups: Control, AFB1 (60 μg/kg), 4-ME (10 mg/kg), and AFB1 + 4-ME, with 3 replicates per group (n=60/replicate). Dietary 4-ME significantly reduced liver oxidative stress markers by activating the Nrf2 pathway and modulating iron homeostasis. Furthermore, 4-ME suppressed AFB1-induced overexpression of ER stress, autophagy, and apoptosis-related genes, while restoring TOR expression and inhibiting AMPK and Ulk1 upregulation at both gene and protein levels. This demonstrates the efficacy of 4-ME in mitigating ferritinophagy and ferroptosis through the AMPK-TOR-Ulk1 signaling axis in aquatic toxicology applications.

Custom Q&A

What is the molecular formula of 4-Methylesculetin?

The molecular formula of 4-Methylesculetin is C10H8O4.

What is the molecular weight of 4-Methylesculetin?

The molecular weight of 4-Methylesculetin is 192.17 g/mol.

What are the synonyms of 4-Methylesculetin?

The synonyms of 4-Methylesculetin are 6,7-DIHYDROXY-4-METHYLCOUMARIN and Methylesculetin.

What is the IUPAC name of 4-Methylesculetin?

The IUPAC name of 4-Methylesculetin is 6,7-dihydroxy-4-methylchromen-2-one.

What is the InChI representation of 4-Methylesculetin?

The InChI representation of 4-Methylesculetin is InChI=1S/C10H8O4/c1-5-2-10(13)14-9-4-8(12)7(11)3-6(5)9/h2-4,11-12H,1H3.

What is the InChIKey of 4-Methylesculetin?

The InChIKey of 4-Methylesculetin is KVOJTUXGYQVLAJ-UHFFFAOYSA-N.

What is the canonical SMILES of 4-Methylesculetin?

The canonical SMILES of 4-Methylesculetin is CC1=CC(=O)OC2=CC(=C(C=C12)O)O.

What is the CAS number of 4-Methylesculetin?

The CAS number of 4-Methylesculetin is 529-84-0.

How many hydrogen bond donor counts does 4-Methylesculetin have?

4-Methylesculetin has 2 hydrogen bond donor counts.

What is the topological polar surface area of 4-Methylesculetin?

The topological polar surface area of 4-Methylesculetin is 66.8 Ų.