Biochanin A

Biochanin A
Names
	Preferred IUPAC name 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
	Other names Biochanin; 4′-Methylgenistein; olmelin; Biochanine A; Biochanin-A; Genistein 4-methyl ether; 5,7-Dihydroxy-4′-methoxyisoflavone
Identifiers
CAS Number	491-80-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17574 ;
ChEMBL	ChEMBL131921 ;
ChemSpider	4444068 ;
ECHA InfoCard	100.007.041
IUPHAR/BPS	2829;
KEGG	C00814 ;
PubChem CID	5280373;
UNII	U13J6U390T ;
CompTox Dashboard (EPA)	DTXSID1022394 ;
	show InChI
	show SMILES
Properties
Chemical formula	C16H12O5
Molar mass	284.267 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	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]

Biochanin A can block the vasoconstriction in a dose-dependent manner due to the inhibition of L-type calcium channels. Such vasodilatory effect, in micromolar concentrations, is of potential clinical interest for the management of cardiovascular pathologies.^[3]

Metabolism[]

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).

References[]

^ 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.
^ Migkos, T., Pourová, J., Vopršalová, M., Auger, C., Schini-Kerth, V., & Mladěnka, P. (2020). "Biochanin A, the Most Potent of 16 Isoflavones, Induces Relaxation of the Coronary Artery Through the Calcium Channel and cGMP-dependent Pathway". Planta medica, 86(10), 708-716. PMID 32408360 doi:10.1055/a-1158-9422

[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.

[2] 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.

[3] Migkos, T., Pourová, J., Vopršalová, M., Auger, C., Schini-Kerth, V., & Mladěnka, P. (2020). "Biochanin A, the Most Potent of 16 Isoflavones, Induces Relaxation of the Coronary Artery Through the Calcium Channel and cGMP-dependent Pathway". Planta medica, 86(10), 708-716. PMID 32408360 doi:10.1055/a-1158-9422

[1]

[2]

[3]

show v t Isoflavones and their glycosides
Isoflavones	Daidzein Genistein Orobol
O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin
Glycosides	Daidzin Genistin Iridin Mirificin Ononin Puerarin Sophoricoside Tectoridin
Prenylated isoflavones	Derrubone Luteone 7-O-Methylluteone Wighteone
Pyranoisoflavones	Alpinumisoflavone Barbigerone
Derivatives	and Irilone Pseudobaptigenin Rotenoids
Synthetic	Ipriflavone

show v t Estrogen-related receptor modulators
ERRα	Agonists: Biochanin A Bisphenol AF Cholesterol Daidzein Genistein Antagonists: Diethylstilbestrol XCT-790
ERRβ	Agonists: Antagonists: 4-Hydroxytamoxifen (afimoxifene) Bisphenol AF Diethylstilbestrol
ERRγ	Agonists: Bisphenol A Antagonists: 4-Hydroxytamoxifen (afimoxifene) Diethylstilbestrol
See also Receptor/signaling modulators

Names


Preferred IUPAC name 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Other names Biochanin 4′-Methylgenistein olmelin Biochanine A Biochanin-A Genistein 4-methyl ether 5,7-Dihydroxy-4′-methoxyisoflavone
Identifiers
CAS Number	491-80-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17574^Y
ChEMBL	ChEMBL131921^Y
ChemSpider	4444068^Y
ECHA InfoCard	100.007.041
IUPHAR/BPS	2829
KEGG	C00814^Y
PubChem CID	5280373
UNII	U13J6U390T^Y
CompTox Dashboard (EPA)	DTXSID1022394
show InChI InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3^Y Key: WUADCCWRTIWANL-UHFFFAOYSA-N^Y InChI=1/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3 Key: WUADCCWRTIWANL-UHFFFAOYAM
show SMILES O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O
Properties
Chemical formula	C₁₆H₁₂O₅
Molar mass	284.267 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Biochanin A

Metabolism[]

See also[]

References[]