Formononetin

Formononetin
Names


IUPAC name 7-hydroxy-3-(4-methoxyphenyl)chromen-4-one
Other names Biochanin B Formononetol 7-Hydroxy-4'-methoxyisoflavone 4'-O-methyldaidzein
Identifiers
CAS Number	485-72-3^Y
3D model (Jmol)	Interactive image
Beilstein Reference	237979
ChEBI	CHEBI:18088^Y
ChEMBL	ChEMBL242341^Y
ChemSpider	4444070^Y
ECHA InfoCard	100.006.931
KEGG	C00858^Y
PubChem	5280378
InChI InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3^Y Key: HKQYGTCOTHHOMP-UHFFFAOYSA-N^Y InChI=1/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3 Key: HKQYGTCOTHHOMP-UHFFFAOYAJ
SMILES O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3
Properties
Chemical formula	C₁₆H₁₂O₄
Molar mass	268.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Formononetin is an O-methylated isoflavone.

Natural occurrences

Formononetin is found in a number of plants and herbs like the red clover.^[1] Along with other phytoestrogens, it predominantly occurs in leguminous plants and Fabaceae, particularly in beans, such as green beans, lima beans, soy and many others, as the free aglycone or in form of its glucoside ononin.^[2]

It can also be found in Maackia amurensis cell cultures.^[3]

The enzyme 4'-methoxyisoflavone 2'-hydroxylase uses formononetin, NADPH, H⁺, and O₂ to produce 2'-hydroxyformononetin, NADP⁺ and H₂O.

The enzyme Isoflavone 3'-hydroxylase uses formononetin, NADPH, H⁺, and O₂ to produce calycosin (3'-hydroxyformononetin), NADP⁺ and H₂O.

Ononin is the 7-O-glucoside of formononetin.

↑ Medjakovic, S.; Jungbauer, A. (2008). "Red Clover Isoflavones Biochanin A and Formononetin are Potent Ligands of the Human Aryl Hydrocarbon Receptor". The Journal of Steroid Biochemistry and Molecular Biology. 108 (1–2): 171–177. doi:10.1016/j.jsbmb.2007.10.001. PMID 18060767.
↑ "Iowa State University Database on the Isoflavone Content of Foods, Release 1.3". USDA. 2002.
↑ Isoflavonoid production by callus cultures of Maackia amurensis. S.A Fedoreyev, T.V Pokushalov, M.V Veselova, L.I Glebko, N.I Kulesh, T.I Muzarok, L.D Seletskaya, V.P Bulgakov and Yu.N Zhuravlev, Fitoterapia, 1 August 2000, Volume 71, Issue 4, Pages 365–372, doi:10.1016/S0367-326X(00)00129-5

Isoflavones and their glycosides

Isoflavones	Daidzein Genistein Irilone Orobol Pseudobaptigenin Anagyroidisoflavone A and B

O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin

Glycosides	Daidzin Genistin Iridin Ononin Puerarin Sophoricoside Tectoridin

Prenylated isoflavones	Bidwillol A Derrubone Luteone 7-O-Methylluteone Wighteone

Pyranoisoflavones	Alpinumisoflavone Barbigerone Di-O-methylalpinumisoflavone 4'-methyl-alpinumisoflavone

Misc	Rotenoids

Synthetic	Ipriflavone

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