A furanochromone with diverse biological activities
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Visnagin

Item No. 34140

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-methoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one
CAS Number
82-57-5
Synonyms
  • NSC 100593
Molecular Formula
C13H10O4
Formula Weight
230.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:5): 0.16 mg/mlDMSO: 5 mg/mlEthanol: 1 mg/ml
λmax
244 nm
SMILES
O=C1C=C(C)OC2=C1C(OC)=C3C=COC3=C2
InChi Code
InChI=1S/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3
InChi Key
NZVQLVGOZRELTG-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $35

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    500 mg

    $85

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    1 g

    $135

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    Cayman Chemical
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    Product Description

    Visnagin is a polyketide synthase-derived furanochromone originally isolated from A. visnaga that has diverse biological activities.1,2,3,4,5 It inhibits the germination and growth of ryegrass (IC50s = 502 and 214 µM, respectively).2 Visnagin (100 µg/ml) is cytotoxic to, and induces apoptosis in, HT-144 melanoma cells.3 It reduces LPS-stimulated increases in the secretion of TNF-α, IL-1β, and IFN-γ in BV-2 microglial cells when used at concentrations of 50 and 100 µM.4 Visnagin (25 mg/kg) protects against cardiomyopathy induced by doxorubicin (Item No. 15007) in mice.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Abe, I. Engineering of plant polyketide biosynthesis. Chem. Pharm. Bull. (Tokyo) 56(11), 1505-1514 (2008).

    2. Travaini, M.L., Sosa, G.M., Ceccarelli, E.A., et al. Khellin and visnagin, furanochromones from Ammi visnaga (L.) Lam., as potential bioherbicides. J. Agric. Food Chem. 64(50), 9475-9487 (2016).

    3. Aydoğmuş-Öztürk, F., Jahan, H., Beyazit, N., et al. The anticancer activity of visnagin, isolated from Ammi visnaga L., against the human malignant melanoma cell lines, HT 144. Mol. Biol. Rep. 46(2), 1709-1714 (2019).

    4. Lee, J.-K., Jung, J.-S., Park, S.-H., et al. Anti-inflammatory effect of visnagin in lipopolysaccharide-stimulated BV-2 microglial cells. Arch. Pharm. Res. 33(11), 1843-1850 (2010).

    5. Liu, Y., Asnani, A., Zou, L., et al. Visnagin protects against doxorubicin-induced cardiomyopathy through modulation of mitochondrial malate dehydrogenase. Sci. Transl. Med. 6(266), 266ra170 (2014).