Natural resveratrol analog
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Isomer(s)
35813Ononetin
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Rhapontigenin

Item No. 13293

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,3-benzenediol
CAS Number
500-65-2
Molecular Formula
C15H14O4
Formula Weight
258.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
222, 326 nm
SMILES
COc1ccc(/C=C\c2cc(O)cc(O)c2)cc1O
InChi Code
InChI=1S/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+
InChi Key
PHMHDRYYFAYWEG-NSCUHMNNSA-N
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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    1 mg

    $61

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    5 mg

    $137

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    10 mg

    $242

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    25 mg

    $379

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    Cayman Chemical
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    Product Description

    Rhapontigenin is a natural analog of resveratrol with antioxidant and anti-cancer activity. It is a mechanism-based, selective inactivator of cytochrome P450 1A1 (IC50 = 400 nM), an aryl hydrocarbon hydroxylase which activates polycyclic aromatic hydrocarbons that act as procarcinogens.1 At higher concentrations, rhapontigenin inhibits the proliferation of HepG2 and HL-60R cancer cell lines (IC50 = 48 μM).2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chun, Y.J., Ryu, S.Y., Jeong, T.C., et al. Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin. Drug Metab. Dispos. 29(4), 389-393 (2001).

    2. Roupe, K.A., Helms, G.L., Halls, S.C., et al. Preparative enzymatic synthesis and HPLC analysis of rhapontigenin: Applications to metabolism, pharmacokinetics and anti-cancer studies. J. Pharm. Pharm. Sci. 8(3), 374-386 (2005).

    3. Roberti, M., Pizzirani, D., Simoni, D., et al. Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J. Med. Chem. 46(16), 3546-3554 (2003).