Genistein

Genistein
Names
	IUPAC name 4′,5,7-Trihydroxyisoflavone
	Systematic IUPAC name 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Identifiers
CAS Number	446-72-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	263823
ChEBI	CHEBI:28088 ;
ChEMBL	ChEMBL44 ;
ChemSpider	4444448 ;
DrugBank	DB01645 ;
ECHA InfoCard	100.006.524
EC Number	207-174-9;
IUPHAR/BPS	2826;
KEGG	D11680 ; C06563;
PubChem CID	5280961;
UNII	DH2M523P0H ;
CompTox Dashboard (EPA)	DTXSID5022308 ;
	InChI InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H Key: TZBJGXHYKVUXJN-UHFFFAOYSA-N ; InChI=1/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H Key: TZBJGXHYKVUXJN-UHFFFAOYAH;
	SMILES Oc1ccc(cc1)C\3=C\Oc2cc(O)cc(O)c2C/3=O;
Properties
Chemical formula	C15H10O5
Molar mass	270.240 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Genistein (C₁₅H₁₀O₅) is a plant-derived, aglycone isoflavone.^[1] Genistein has the highest content of all isoflavones in soybeans and soy products, such as tempeh. As a type of phytoestrogen, genistein has estrogenic activity in vitro; consequently, its long-term intake by consuming soy products may affect reproductive organs, such as the uterus and breast.^[1]

It was first isolated in 1899 from the dyer's broom, Genista tinctoria; hence, the chemical name. The compound structure was established in 1926, when it was found to be identical with that of prunetol. It was chemically synthesized in 1928.^[2] Genistein is a primary secondary metabolite of the Trifolium species and Glycine max (soy).

^ ^a ^b "Soy isoflavones". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2025. Retrieved 9 April 2025.
^ Walter ED (1941). "Genistin (an Isoflavone Glucoside) and its Aglucone, Genistein, from Soybeans". Journal of the American Chemical Society. 63 (12): 3273–76. Bibcode:1941JAChS..63.3273W. doi:10.1021/ja01857a013.

[lpi-1] "Soy isoflavones". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2025. Retrieved 9 April 2025.

[2] Walter ED (1941). "Genistin (an Isoflavone Glucoside) and its Aglucone, Genistein, from Soybeans". Journal of the American Chemical Society. 63 (12): 3273–76. Bibcode:1941JAChS..63.3273W. doi:10.1021/ja01857a013.

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