Isoxanthohumol

Isoxanthohumol is a prenylflavonoid, and it is a phytoestrogen. It is abbreviated as IX or IXN.

Isoxanthohumol

Names
IUPAC name 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Identifiers
CAS Number	70872-29-6 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL492828
ChemSpider	8104156
KEGG	C22606
PubChem CID	513197
InChI InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3/t18-/m0/s1 Key: YKGCBLWILMDSAV-SFHVURJKSA-N InChI=1/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3/t18-/m0/s1 Key: YKGCBLWILMDSAV-SFHVURJKBQ
SMILES O=C2c3c(O[C@H](c1ccc(O)cc1)C2)c(c(O)cc3OC)C\C=C(/C)C
Properties
Chemical formula	C21H22O5
Molar mass	354.402 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 can be produced from isoxanthohumol by flora in the human intestine,^[1] and by fungi in cell cultures.^[2]

This prenylflavonoid is found in hops and beer. It has limited estrogenic activity. At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.^[3]

Derivatives of isoxanthohumol are: 7,4′-Di-O-methylisoxanthohumol; 7-O-methylisoxanthohumol; 7-O-n-pentylisoxanthohumol; 7,4′-di-O-n-pentyl-8-isoxanthohumol; 7,4′-Di-O-allylisoxanthohumol; 7,4′-Di-O-acetylisoxanthohumol; and 7,4′-Di-O-palmitoylisoxanthohumol.^[4]

See also

• Xanthohumol, the corresponding prenylated chalcone