A methoxylated flavone with diverse biological activities
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Ermanin

Item No. 37535

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,7-dihydroxy-3-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
CAS Number
20869-95-8
Synonyms
  • 5,7-Dihydroxy-3,4′-dimethoxyflavone
  • Kaempferol 3,4′-di-O-methyl ether
  • NSC 31882
Molecular Formula
C17H14O6
Formula Weight
314.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 15 mg/ml
λmax
269, 349 nm
SMILES
O=C1C(OC)=C(C2=CC=C(OC)C=C2)OC3=C1C(O)=CC(O)=C3
InChi Code
InChI=1S/C17H14O6/c1-21-11-5-3-9(4-6-11)16-17(22-2)15(20)14-12(19)7-10(18)8-13(14)23-16/h3-8,18-19H,1-2H3
InChi Key
RJCJVIFSIXKSAH-UHFFFAOYSA-N
Origin
Plant/Grapes
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $40

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    10 mg

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    25 mg

    $179

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    50 mg

    $315

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    Product Description

    Ermanin is a methoxylated flavone that has been found in bee glue and has diverse biological activities.1,2,3 It increases the levels of intracellular reactive oxygen species (ROS) and decreases the levels of glutathione (GSH) in B16/F10 mouse melanoma cells and primary mouse melanocytes when used at concentrations of 8 and 16 µM.1 Ermanin reduces LPS-induced increases in inducible nitric oxide synthase (iNOS) and COX-2 levels in RAW 264.7 mouse macrophages (IC50s = 6.7 and 1.68 µM, respectively).2 It inhibits viral replication of poliovirus type 1 in Vero cells (ED99 = 5 µg/ml).3 Ermanin (8 and 16 µM) induces melanogenesis in zebrafish larvae.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ding, Q., Luo, L., Yu, L., et al. The critical role of glutathione redox homeostasis towards oxidation in ermanin-induced melanogenesis. Free Radic. Biol. Med. 176, 392-405 (2021).

    2. Guerra, J.A., Molina, M.F., Abad, M.J., et al. Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids isolated from Tanacetum microphyllum. Int. Immunopharmacol. 6(11), 1723-1728 (2006).

    3. De Meyer, N., Haemers, A., Mishra, L., et al. 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity. J. Med. Chem. 34(2), 736-746 (1991).