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 naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen.^[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] It has been shown to be the primary secondary metabolite of the Trifolium species and Glycine max.^[3]

^ Sail, Vibhavari; Hadden, M. Kyle (2012-01-01), "Notch Pathway Modulators as Anticancer Chemotherapeutics", in Desai, Manoj C. (ed.), Chapter Eighteen - Notch Pathway Modulators as Anticancer Chemotherapeutics, Annual Reports in Medicinal Chemistry, vol. 47, Academic Press, pp. 267–280, doi:10.1016/B978-0-12-396492-2.00018-7, ISBN 978-0-12-396492-2, retrieved 2020-09-14
^ Walter, E. D. (1941). "Genistin (an Isoflavone Glucoside) and its Aglucone, Genistein, from Soybeans". Journal of the American Chemical Society. 63 (12): 3273–76. doi:10.1021/ja01857a013.
^ Popiołkiewicz, Joanna; Polkowski, Krzysztof; Skierski, Janusz S.; Mazurek, Aleksander P. (November 2005). "In vitro toxicity evaluation in the development of new anticancer drugs—genistein glycosides". Cancer Letters. 229 (1): 67–75. doi:10.1016/j.canlet.2005.01.014. ISSN 0304-3835. PMID 16157220.

[1] Sail, Vibhavari; Hadden, M. Kyle (2012-01-01), "Notch Pathway Modulators as Anticancer Chemotherapeutics", in Desai, Manoj C. (ed.), Chapter Eighteen - Notch Pathway Modulators as Anticancer Chemotherapeutics, Annual Reports in Medicinal Chemistry, vol. 47, Academic Press, pp. 267–280, doi:10.1016/B978-0-12-396492-2.00018-7, ISBN 978-0-12-396492-2, retrieved 2020-09-14

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

[3] Popiołkiewicz, Joanna; Polkowski, Krzysztof; Skierski, Janusz S.; Mazurek, Aleksander P. (November 2005). "In vitro toxicity evaluation in the development of new anticancer drugs—genistein glycosides". Cancer Letters. 229 (1): 67–75. doi:10.1016/j.canlet.2005.01.014. ISSN 0304-3835. PMID 16157220.

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