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Rhapontigenin Exclusive

Cayman Chemical Item Number 13293

(CAS 500-65-2)

Rhapontigenin (CAS 500-65-2)

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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 Hep-G2 and HL-60R cancer cell lines (IC50 = 48 μM).2,3

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 3546-3554 (2003).

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
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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COc1ccc(/C=C\c2cc(O)​cc(O)​c2)​cc1O

Background Reading

Ohinata, Y., Payer, B., O'Carroll, D., et al. Blimp1 is a critical determinant of the germ cell lineage in mice. Nature 436 207-213 (2005).

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).

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

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).

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Rhapontigenin is available in the following screening library:

Size Price Quantity Subtotal
1 mg $72.00 $0.00
5 mg $324.00 $0.00
10 mg $576.00 $0.00
25 mg $1,260.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

cis-Resveratrol
Cytochrome P450 1A1 (human) Yeast Reductase
trans-Resveratrol

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