isoxanthohumol

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| ImageFile = Isoxanthohumol.svg

| ImageSize = 250px

| ImageAlt = Chemical structure of isoxanthohumol.

| IUPACName = 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

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|Section1={{Chembox Identifiers

| CASNo = 70872-29-6

| CASNo_Ref = {{Cascite|changed|CAS}}

| ChEMBL = 492828

| KEGG = C22606

| PubChem = 513197

| ChemSpiderID = 8104156

| SMILES = O=C2c3c(O[C@H](c1ccc(O)cc1)C2)c(c(O)cc3OC)C\C=C(/C)C

| 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

| InChIKey = YKGCBLWILMDSAV-SFHVURJKBQ

| StdInChI = 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

| StdInChIKey = YKGCBLWILMDSAV-SFHVURJKSA-N

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|Section2={{Chembox Properties

| C=21 | H=22 | O=5

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|Section3={{Chembox Hazards

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

8-Prenylnaringenin can be produced from isoxanthohumol by flora in the human intestine,{{cite journal |vauthors=Possemiers S, Bolca S, Grootaert C, Heyerick A, Decroos K, Dhooge W, De Keukeleire D, Rabot S, Verstraete W, Van de Wiele T|display-authors=etal |title=The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine |journal=Journal of Nutrition |volume=136 |issue=7 |pages=1862–7 |year=2006 |pmid=16772450 |doi= 10.1093/jn/136.7.1862|url=http://jn.nutrition.org/content/136/7/1862.long|doi-access=free }} and by fungi in cell cultures.{{Cite journal|doi=10.1021/jf2011722|title=Production of 8-Prenylnaringenin from Isoxanthohumol through Biotransformation by Fungi Cells|year=2011|last1=Fu|first1=Ming-Liang|last2=Wang|first2=Wei|last3=Chen|first3=Feng|last4=Dong|first4=Ya-Chen|last5=Liu|first5=Xiao-jie|last6=Ni|first6=Hui|last7=Chen|first7=Qi-he|journal=Journal of Agricultural and Food Chemistry|volume=59|issue=13|pages=7419–26|pmid=21634799}}

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.{{Cite journal|doi=10.1002/mnfr.200900519|pmid=20486208|title=Disposition of hop prenylflavonoids in human breast tissue|year=2010|last1=Bolca|first1=Selin|last2=Li|first2=Jinghu|last3=Nikolic|first3=Dejan|last4=Roche|first4=Nathalie|last5=Blondeel|first5=Phillip|last6=Possemiers|first6=Sam|last7=De Keukeleire|first7=Denis|last8=Bracke|first8=Marc|last9=Heyerick|first9=Arne|last10=Van Breemen|first10=Richard B.|last11=Depypere|first11=Herman|journal=Molecular Nutrition & Food Research|volume=54|issue=2 |pages=S284–94|pmc=3856213}}

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.{{cite journal |vauthors=Anioł M, Swiderska A, Stompor M, Zołnierczyk AK |title=Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4'-O-substituted isoxanthohumols |journal=Med Chem Res |volume=21 |issue=12 |pages=4230–4238 |year=2012 |pmid=23087590 |pmc=3474914 |doi=10.1007/s00044-011-9967-8}}