A chalcone with diverse biological activities
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Analytical Standard(s)
40957Flavokawain A (CRM)
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Flavokawain A

Item No. 36083

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one
CAS Number
37951-13-6
Synonyms
  • Flavokavain A
  • 4-methoxy Flavokawain B
Molecular Formula
C18H18O5
Formula Weight
314.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 2 mg/ml
λmax
361 nm
SMILES
COC1=C(C(O)=CC(OC)=C1)C(/C=C/C2=CC=C(C=C2)OC)=O
InChi Code
InChI=1S/C18H18O5/c1-21-13-7-4-12(5-8-13)6-9-15(19)18-16(20)10-14(22-2)11-17(18)23-3/h4-11,20H,1-3H3/b9-6+
InChi Key
CGIBCVBDFUTMPT-RMKNXTFCSA-N
Origin
Plant/Piper methysticum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $54

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    10 mg

    $97

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    25 mg

    $229

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    50 mg

    $432

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    Cayman Chemical
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    Product Description

    Flavokawain A is a chalcone that has been found in P. methysticum and has diverse biological activities.1,2,3 It activates nuclear factor erythroid 2-related factor 2 (Nrf2) and heat shock factor 1 (Hsf1; EC50s = 14.1 and 7.9 µM, respectively, in reporter assays), increases glutathione (GSH) levels, and protects against hydrogen peroxide-induced cytotoxicity in HepG2 cells.1 Flavokawain A (10 and 20 µM) inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS), COX-2, nitric oxide (NO), and prostaglandin E2 (PGE2; Item No. 14010) levels in RAW 264.7 macrophages.2 It induces apoptosis in T24 bladder cancer cells when used at a concentration of 12.5 µg/ml.3 Flavokawain A (50 mg/kg) reduces tumor growth in an EJ bladder cancer mouse xenograft model.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pinner, K.D., Wales, C.T.K., Gristock, R.A., et al. Flavokawains A and B from kava (Piper methysticum) activate heat shock and antioxidant responses and protect against hydrogen peroxide-induced cell death in HepG2 hepatocytes. Pharm. Biol. 54(9), 1503-1512 (2016).

    2. Kwon, D.-J., Ju, S.M., Youn, G.S., et al. Suppression of iNOS and COX-2 expression by flavokawain A via blockade of NF-κB and AP-1 activation in RAW 264.7 macrophages. Food Chem. Toxicol. 58, 479-486 (2013).

    3. Zi, X., and Simoneau, A.R. Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice. Cancer Res. 65(8), 3479-3486 (2005).