A synthetic coumarin with diverse biological activities
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5,7-Dihydroxy-4-methylcoumarin

Item No. 33756

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,7-dihydroxy-4-methyl-2H-1-benzopyran-2-one
CAS Number
2107-76-8
Synonyms
  • NSC 5302
Molecular Formula
C10H8O4
Formula Weight
192.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:3): 0.25 mg/mlEthanol: 20 mg/ml
λmax
325 nm
SMILES
O=C1OC2=C(C(C)=C1)C(O)=CC(O)=C2
InChi Code
InChI=1S/C10H8O4/c1-5-2-9(13)14-8-4-6(11)3-7(12)10(5)8/h2-4,11-12H,1H3
InChi Key
QNVWGEJMXOQQPM-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

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    Cayman Chemical
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    Product Description

    5,7-Dihydroxy-4-methylcoumarin is a synthetic coumarin with diverse biological activities.1,2,3,4,5,6,7 It scavenges alkylperoxy radicals and hypochlorous acid (HOCl; IC50 = 2.85 µM) in cell-free assays, as well as inhibits lipid peroxidation in rat liver microsomes, A23187-induced thromboxane B2 (TXB2; Item No. 19030) generation in isolated rat peritoneal leukocytes, and myeloperoxidase (MPO) activity in a cell-free assay (IC50s = 12, 1, and 1.06 µM, respectively).1,2 5,7-Dihydroxy-4-methylcoumarin also inhibits rat lens aldose reductase (IC50 = 17 µM) and human carbonic anhydrase I (CAI), CAIX, and CAXII with Ki values of 8.4, 0.19, and 6.4 µM, respectively.3,4 It inhibits platelet aggregation induced by arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) with an IC50 value of 45 µM.6 5,7-Dihydroxy-4-methylcoumarin inhibits hepatitis C virus (HCV) non-structural protein 5B (NS5B) polymerase (IC50 = 47.2 µM).5 It is active against H. pylori with an MIC value of 10 µg/ml.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hoult, J.R.S., and Payá, M. Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential. Gen. Pharmacol. 27(4), 713-722 (1996).

    2. Kabeya, L.M., Fuzissaki, C.N., Andrade, M.F., et al. 4-methylcoumarin derivatives inhibit human neutrophil oxidative metabolism and elastase activity. J. Med. Food 16(8), 692-700 (2013).

    3. Brubaker, A.N., DeRuiter, J., and Whitmer, W.L. Synthesis and rat lens aldose reductase inhibitory activity of some benzopyran-2-ones. J. Med. Chem. 29(6), 1094-1099 (1986).

    4. Sharma, A., Tiwari, M.N., and Supuran, C.T. Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX. J. Enzyme Inhib. Med. Chem. 29(2), 292-296 (2014).

    5. Nichols, D.B., Leão, R.A.C., Basu, A., et al. Evaluation of coumarin and neoflavone derivatives as HCV NS5B polymerase inhibitors. Chem. Biol. Drug Des. 81(5), 607-614 (2013).

    6. Macáková, K., Řeháková, Z., Mladěnka, P., et al. In vitro platelet antiaggregatory properties of 4-methylcoumarins. Biochimie 94(12), 2681-2686 (2012).

    7. Jadhav, S.G., Meshram, R.J., Gond, D.S., et al. Inhibition of growth of Helicobacter pylori and its urease by coumarin derivatives: Molecular docking analysis. J. Pharm. Res. 7(8), 705-711 (2013).