Rhapontigenin

Rhapontigenin is a stilbenoid. It can be isolated from Vitis coignetiae or from Gnetum cleistostachyum.^[1]

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Rhapontigenin

Names
Preferred IUPAC name 5-[(E)-2-(3-Hydroxy-4-methoxyphenyl)ethen-1-yl]benzene-1,3-diol
Other names Protigenin 3,3',5-trihydroxy-4'-methoxystilbene piceatannol 4'-methyl ether
Identifiers
CAS Number	500-65-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:174376
ChEMBL	ChEMBL113029
ChemSpider	4478875
PubChem CID	5320954
UNII	22BG4NNH6W Y
CompTox Dashboard (EPA)	DTXSID501023634
InChI 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+ Key: PHMHDRYYFAYWEG-NSCUHMNNSA-N
SMILES COc1ccc(cc1O)\C=C\c(cc2O)cc(O)c2
Properties
Chemical formula	C15H14O4
Molar mass	258.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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It shows an action on prostate cancer cells.^[2] It has been shown to inhibit the human cytochrome P450 1A1,^[3] an enzyme implicated in the biotransformation of a number of carcinogenic and immunotoxic compounds.

Injected in rats, rhapontigenin shows a rapid glucuronidation and a poor bioavailability.^[4]