A flavonoid with diverse biological activities
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Isomer(s)
40217Ombuin 35835Tricin
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Cirsiliol

Item No. 30874

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-1-benzopyran-4-one
CAS Number
34334-69-5
Synonyms
  • Crisiliol
Molecular Formula
C17H14O7
Formula Weight
330.3
Purity
≥90%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
Acetone: solubleChloroform: solubleDMSO: soluble
λmax
213, 273, 346 nm
SMILES
OC1=C(O)C=CC(C(OC2=C3C(O)=C(OC)C(OC)=C2)=CC3=O)=C1
InChi Code
InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3
InChi Key
IMEYGBIXGJLUIS-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $128

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    10 mg

    $236

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    25 mg

    $502

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    Product Description

    Cirsiliol is a flavonoid that has been found in S. indicum and has diverse biological activities.1 It inhibits 5-lipoxygenase (5-LO) and 12-LO (IC50s = 0.1 and 1 µM, respectively).1 Cirsiliol inhibits the release of slow-reacting substance of anaphylaxis (SRS-A) in passively sensitized isolated guinea pig lung (IC50 = 0.4 µM). It induces relaxation of precontracted isolated rat uterus, urinary bladder, proximal aorta, and trachea in a concentration-dependent manner.2 Cirsiliol inhibits colony formation and migration of B16/F10 murine melanoma cells.3 In vivo, cirsiliol (200 µg/kg) enhances radiation-induced inhibition of tumor growth in an H1299 non-small cell lung cancer (NSCLC) mouse xenograft model.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yoshimoto, T., Furukawa, M., Yamamoto, S., et al. Flavonoids: Potent inhibitors of arachidonate 5-lipoxygenase. Biochem. Biophys. Res. Commun. 116(2), 612-618 (1983).

    2. Mustafa, E.H., Zarga, M.A., Sabri, S., et al. Effects of cirsiliol, a flavone isolated from Achillea fragrantissima, on rat isolated smooth muscle. Int. J. Pharm. 33(3), 204-209 (1995).

    3. Prasad, P., Vasas, A., Hohmann, J., et al. Cirsiliol suppressed epithelial to mesenchymal transition in B16F10 malignant melanoma cells through alteration of the PI3K/Akt/NF-κB signaling pathway. Int. J. Mol. Sci. 20(3), 608 (2019).

    4. Kang, J., Kim, E., Kim, W., et al. Rhamnetin and cirsiliol induce radiosensitization and inhibition of epithelial-mesenchymal transition (EMT) by miR-34a-mediated suppression of Notch-1 expression in non-small cell lung cancer cell lines. The Journal of Biological Chemisty 288(38), 27343-27357 (2013).