biochanin A

{{chembox

| Watchedfields = changed

| verifiedrevid = 443423335

| Name = Biochanin A

| ImageFile = Biochanin A.svg

| ImageSize = 220px

| ImageFile1 = Biochanin-A-3D-balls.png

| ImageSize1 = 220

| ImageAlt1 = Biochanin A molecule

| IUPACName = 5,7-Dihydroxy-4′-methoxyisoflavone

| SystematicName = 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one

| OtherNames = Biochanin
4′-Methylgenistein
olmelin
Biochanine A
Biochanin-A
Genistein 4-methyl ether

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 2829

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4444068

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C00814

| 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

| InChIKey = WUADCCWRTIWANL-UHFFFAOYAM

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 131921

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WUADCCWRTIWANL-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 491-80-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = U13J6U390T

| PubChem = 5280373

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 17574

| SMILES = O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O

}}

|Section2={{Chembox Properties

| C=16 | H=12 | O=5

| Appearance =

| Density =

| MeltingPt =

| BoilingPt=

| Solubility=

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|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt=

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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{{ cite journal |author1=Medjakovic, S. |author2=Jungbauer, A. | title = Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor | journal = The Journal of Steroid Biochemistry and Molecular Biology | year = 2008 | volume = 108 | issue = 1–2 | pages = 171–177 | pmid = 18060767 | doi = 10.1016/j.jsbmb.2007.10.001 |s2cid=206495959 }} 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.{{medcn|date=November 2015}} It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro.{{cite journal | vauthors=Thors L, Burston JJ, Alter BJ, McKinney MK, Cravatt BF, Ross RA, Pertwee RG, Gereau RW, Wiley JL, Fowler CJ | title = Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase | journal = British Journal of Pharmacology | year = 2010 | volume = 160 | issue = 3 | pages = 549–560 | doi = 10.1111/j.1476-5381.2010.00716.x | pmid = 20590565 | pmc = 2931556 }}