8-Prenylnaringenin

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-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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • 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
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-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.

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