Biochanin A
Names | |
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IUPAC name
5,7-Dihydroxy-3-(4-methoxyphenyl)chromen-4-one
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Other names
Biochanin
4'-Methylgenistein olmelin Biochanine A Biochanin-A Genistein 4-methyl ether 5,7-Dihydroxy-4'-methoxyisoflavone |
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Identifiers | |
491-80-5 Y | |
3D model (Jmol) | Interactive image |
ChEBI | CHEBI:17574 Y |
ChEMBL | ChEMBL131921 Y |
ChemSpider | 4444068 Y |
ECHA InfoCard | 100.007.041 |
2829 | |
KEGG | C00814 Y |
PubChem | 5280373 |
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Properties | |
C16H12O5 | |
Molar mass | 284.27 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Y verify (what is YN ?) | |
Infobox references | |
Biochanin A is an O-methylated isoflavone. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A can be found in red clover [1] in soy, in alfalfa sprouts, in peanuts, in chickpea (Cicer arietinum) and in other legumes.
Biochanin A is classified as a phytoestrogen and has putative benefits in dietary cancer prophylaxis.[medical citation needed] It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro.[2]
Metabolism[edit]
The enzyme biochanin-A reductase uses dihydrobiochanin A and NADP+ to produce biochanin A, NADPH, and H+. The enzyme isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase uses malonyl-CoA and biochanin A 7-O-β-D-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-D-glucoside).
See also[edit]
References[edit]
- ^ 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.
- ^ Thors L, Burston JJ, Alter BJ, McKinney MK, Cravatt BF, Ross RA, Pertwee RG, Gereau RW, Wiley JL, Fowler CJ (2010). "Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase". British Journal of Pharmacology. 160 (3): 549–560. doi:10.1111/j.1476-5381.2010.00716.x. PMC 2931556. PMID 20590565.
Isoflavones and their glycosides
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Isoflavones | |
O-methylated isoflavones | |
Glycosides | |
Prenylated isoflavones | |
Pyranoisoflavones | |
Misc | |
Synthetic |
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GPER |
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CAR |
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FXR |
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LXR |
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PPAR |
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PXR |
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RAR |
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RXR |
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SHR |
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TR |
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