A synthetic coumarin with diverse biological activities
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Isomer(s)
308577-Methoxycoumarin
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4-Methylumbelliferone

Item No. 29603

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-hydroxy-4-methyl-2H-1-benzopyran-2-one
CAS Number
90-33-5
Synonyms
  • 4-ΜU
  • Hymecromone
  • 4-Methyl-7-hydroxycoumarin
  • 7-Hydroxy-4-methylcoumarin
Molecular Formula
C10H8O3
Formula Weight
176.2
Purity
≥98%
Emission
445, 455 nm at low and high pH, respectively
Excitation
320, 360 nm at low and high pH, respectively
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 0.25 mg/ml
λmax
218, 325 nm
SMILES
OC1=CC=C(C(C)=CC(O2)=O)C2=C1
InChi Code
InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
InChi Key
HSHNITRMYYLLCV-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    4-Methylumbelliferone (4-ΜU) is a synthetic coumarin with diverse biological activities.1,2,3 It inhibits hyaluronic acid synthesis in PC3-ML and DU145 cells (IC50s = ~0.4 mM for both).1 4-MU inhibits the growth of PC3-ML, DU145, C4-2B, LNCaP, and LAPC-4 prostate cancer cells (IC50s = 0.2-0.4 mM) and invasion and chemotactic motility of PC3-ML and DU145 cells in vitro. It reduces tumor growth and microvessel density in a PC3-ML mouse xenograft model when administered at doses of 225 and 450 mg/kg twice per day. 4-ΜU is active against H. pylori and V. cholerae in vitro (MICs = 59 and 100-200 μg/ml, respectively).2 Derivatives and conjugates of 4-ΜU have been used as fluorogenic substrates to measure enzyme activity.4,5,6 Upon enzymatic cleavage, 4-ΜU is released and its fluorescence can be used to quantify enzyme activity. 4-MU fluorescence is pH-dependent with excitation maxima of 320 and 360 nm at low (1.97-6.72) and high pH (7.12-10.3), respectively, and an emission maximum ranging from 445 to 455 nm, increasing as pH decreases.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lokeshwar, V.B., Lopez, L.E., Munoz, D., et al. Antitumor activity of hyaluronic acid synthesis inhibitor 4-methylumbelliferone in prostate cancer cells. Cancer Res. 70(7), 2613-2623 (2010).

    2. Kawase, M., Varu, B., Shah, A., et al. Antimicrobial activity of new coumarin derivatives. Arzneimittelforschung 51(1), 67-71 (2001).

    3. Zhi, H., Wang, J., Wang, S., et al. Fluorescent properties of hymecromone and fluorimetric analysis of hymecromone in compound dantong capsule. J. Spectrosc. 147128 (2013).

    4. Karpova, E.A., Voznyi, Y.V., Keulemans, J.L.M., et al. A fluorimetric enzyme assay for the diagnosis of Sanfilippo disease type A (MPS IIIA). J. Inherit. Metab. Dis. 19(3), 278-285 (1996).

    5. Kelly, S., and Bakhru-Kishore, R. Fluorimetric assay of acid lipase in human leukocytes. Clin. Chim. Acta 97(2-3), 239-242 (1979).

    6. Wendeler, M., and Sandhoff, K. Hexosaminidase assays. Glycoconj. J. 26(8), 945-952 (2009).