A flavone with diverse biological activities
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5,7,3',4'-Tetramethoxyflavone

Item No. 40272

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-1-benzopyran-4-one
CAS Number
855-97-0
Synonyms
  • 5,7,3’,4’-tetramethyl Luteolin ether
  • Methoxyluteolin
  • Tetramethyl camphoral
Molecular Formula
C19H18O6
Formula Weight
342.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Soluble
SMILES
O=C1C=C(C2=CC(OC)=C(OC)C=C2)OC3=CC(OC)=CC(OC)=C13
InChi Code
InChI=1S/C19H18O6/c1-21-12-8-17(24-4)19-13(20)10-15(25-18(19)9-12)11-5-6-14(22-2)16(7-11)23-3/h5-10H,1-4H3
InChi Key
CLXVBVLQKLQNRQ-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $39

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    50 mg

    $74

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    100 mg

    $131

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    250 mg

    $308

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    Cayman Chemical
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    Product Description

    5,7,3',4'-Tetramethoxyflavone is a flavone that has been found in M. paniculata and has diverse biological activities.1,2,3,4,5,6 It selectively inhibits multidrug resistance-associated protein 1 (MRP1) over MRP2 (IC50s = 7.9 and >50 µM, respectively).1 5,7,3',4'-Tetramethoxyflavone (0.03-30 µM) inhibits LPS-induced nitric oxide (NO) release in primary mouse peritoneal macrophages.2 It is active against P. falciparum (IC50 = 4.06 µg/ml).3 5,7,3',4'-Tetramethoxyflavone (20 µM) is cytotoxic to B16/F10 melanoma cells.4 It inhibits IL-33-induced production of chemokine (C-C motif) ligand 2 (CCL2) and CCL5 in primary human mast cells when used at concentrations of 50 and 100 µM.5 In vivo, 5,7,3',4'-tetramethoxyflavone (100 mg/kg) decreases the synovial fluid levels of prostaglandin E2 (PGE2; Item No. 14010), IL-1β, and TNF-α in a rat model of surgically induced osteoarthritis.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. van Zanden, J.J., Wortelboer, H.M., Bijlsma, S., et al. Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2. Biochem. Pharmacol. 69(4), 699-708 (2005).

    2. Wu, J., Liu, K., and Shi, X. The anti-inflammatory activity of several flavonoids isolated from Murraya paniculata on murine macrophage cell line and gastric epithelial cell (GES-1). Pharm. Biol. 54(5), 868-881 (2016).

    3. Yenjai, C., Prasanphen, K., Daodee, S., et al. Bioactive flavonoids from Kaempferia parviflora. Fitoterapia 75(1), 89-92 (2004).

    4. Jung, S.-H., Heo, H.-Y., Choe, J.-W., et al. Anti-melanogenic properties of velutin and its analogs. Molecules 26(10), 3033 (2021).

    5. Bawazeer, M.A., and Theoharides, T.C. IL-33 stimulates human mast cell release of CCL5 and CCL2 via MAPK and NF-κB, inhibited by methoxyluteolin. Eur. J. Pharmacol. 865, 172760 (2019).

    6. Wu, L., Liu, H., Li, L., et al. 5,7,3',4'-Tetramethoxyflavone exhibits chondroprotective activity by targeting β-catenin signaling in vivo and in vitro. Biochem. Biophys. Res. Commun. 452(3), 682-688 (2014).