8-Prenylnaringenin

8-Prenylnaringenin
Names
	IUPAC name (2S)-4′,5,7-Trihydroxy-8-(3-methylbut-2-en-1-yl)flavan-4-one
	Systematic IUPAC name (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-1-benzopyran-4-one
	Other names Hopein; Flavaprenin; Sophoraflavanone B
Identifiers
CAS Number	53846-50-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:50207 ;
ChemSpider	421848;
KEGG	C18023 ;
PubChem CID	480764;
UNII	5L872SZR8X ;
CompTox Dashboard (EPA)	DTXSID60333083 ;
	InChI InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1 Key: LPEPZZAVFJPLNZ-SFHVURJKSA-N; InChI=1/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1 Key: LPEPZZAVFJPLNZ-SFHVURJKBX;
	SMILES CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C;
Properties
Chemical formula	C20H20O5
Molar mass	340.375 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

8-Prenylnaringenin (8-PN; also known as flavaprenin, (S)-8-dimethylallylnaringenin, hopein, or sophoraflavanone B) is a prenylflavonoid phytoestrogen. It is reported to be the most estrogenic phytoestrogen known. The compound is equipotent at the two forms of estrogen receptors, ERα and ERβ, and it acts as a full agonist of ERα. Its effects are similar to those of estradiol, but it is considerably less potent in comparison.

8-PN is found in hops (Humulus lupulus) and in beer, and is responsible for the estrogenic effects of the former. It can be produced from isoxanthohumol in fungal cells cultures, and by flora in the human intestine.