Formononetin

Formononetin

Names
IUPAC name 7-Hydroxy-4′-methoxyisoflavone
Systematic IUPAC name 7-Hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Other names Biochanin B Formononetol 4'-O-methyldaidzein
Identifiers
CAS Number	485-72-3^Y
3D model (JSmol)	Interactive image
Beilstein Reference	237979
ChEBI	CHEBI:18088^Y
ChEMBL	ChEMBL242341^Y
ChemSpider	4444070^Y
ECHA InfoCard	100.006.931
KEGG	C00858^Y
PubChem CID	5280378
UNII	295DQC67BJ^Y
CompTox Dashboard (EPA)	DTXSID4022311
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 such as 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]

Pharmacodynamics

Formononetin promotes angiogenesis.^[4] It is also involved in expressing the gene and proteins that are needed to make IgE.^[5]

Derivatives

Ononin is the 7-O-β-D-glucopyranoside of formononetin.^[6]

References

1. 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. S2CID 206495959.
2. "Iowa State University Database on the Isoflavone Content of Foods, Release 1.3". USDA. 2002. Archived from the original on 2012-11-02. Retrieved 2011-02-13.
3. Fedoreyev, S.A; Pokushalova, T.V; Veselova, M.V; Glebko, L.I; Kulesh, N.I; Muzarok, T.I; Seletskaya, L.D; Bulgakov, V.P; Zhuravlev, Yu.N (2000). "Isoflavonoid production by callus cultures of Maackia amurensis". Fitoterapia. 71 (4): 365–72. doi:10.1016/S0367-326X(00)00129-5. PMID 10925005.
4. Li, Shang; Dang, Yuanye; Zhou, Xuelin; Huang, Bin; Huang, Xiaohui; Zhang, Zherui; Kwan, Yiu Wa; Chan, Shun Wan; Leung, George Pak Heng; Lee, Simon Ming Yuen; Hoi, Maggie Pui Man (2015). "Formononetin promotes angiogenesis through the estrogen receptor alpha-enhanced ROCK pathway". Scientific Reports. 5: 16815. Bibcode:2015NatSR...516815L. doi:10.1038/srep16815. PMC 4645220. PMID 26568398.
5. "This plant-based compound could finally cure food allergies". ZME Science. 2022-04-01. Retrieved 2022-04-04.
6. You-Ping Zhu (1998-05-28). Chinese Materia Medica: Chemistry, Pharmacology and Applications. CRC Press. p. 622. ISBN 9057022850.