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Merck

G6776

Genistein

From Glycine max (soybean), ~98% (HPLC), tyrosine protein kinase inhibitor, powder

Synonym(s):

4′,5,7-Trihydroxyisoflavone, 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

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About This Item

Empirical Formula (Hill Notation):
C15H10O5
CAS Number:
446-72-0
Molecular Weight:
270.24
NACRES:
NA.77
PubChem Substance ID:
24895273
UNSPSC Code:
12352200
EC Number:
207-174-9
MDL number:
MFCD00016952
Beilstein/REAXYS Number:
263823

Product Name

Genistein, from Glycine max (soybean), ~98% (HPLC)

InChI key

TZBJGXHYKVUXJN-UHFFFAOYSA-N

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

SMILES string

Oc1ccc(cc1)C2=COc3cc(O)cc(O)c3C2=O

biological source

Glycine max (soybean)

assay

~98% (HPLC)

form

powder

mp

>280 °C

solubility

DMSO: soluble
ethanol: soluble

storage temp.

−20°C

Quality Level

200

Gene Information

human ... AKT1(207), CYP19A1(1588), EGFR(1956), ESR1(2099), ESR2(2100)
mouse ... Esr1(13982), Hexa(15211)
rat ... Adora1(29290), Adora2a(25369), Ar(24208)

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Application

Genistein has been used:
  • as an anticancer agent to test its cytotoxicity in cervix adenocarcinoma cells
  • as a polyphenol to test its effect on reactive oxygen species in mitochondria from sperm
  • to test its radical scavenging effect on the UV irradiated in dermal and keloid fibroblasts

Biochem/physiol Actions

Genistein has antioxidant functionality and is effective in quenching reactive oxygen species. It is beneficial to human health.
Inhibitor of tyrosine protein kinase; competitive inhibitor of ATP in other protein kinase reactions. Antiangiogenic agent, down-regulates the transcription of genes involved in controlling angiogenesis.

Features and Benefits

This compound is featured on the Met page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

General description

Genistein is a nutraceutical isoflavnoid from soybean and is a phytoestrogen. It is derived from genistin.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000486021
0000486021
0000458669
0000458669
0000404420

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Lin Yang et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 25(3), 928-936 (2010-12-04)
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Ravindranadh Palika et al.
Journal of agricultural and food chemistry, 61(46), 11151-11157 (2013-10-29)
Previously, we have demonstrated increased iron absorption from low molecular weight (LMW) human milk whey fractions. In the present study, we investigated the effect of heat denaturation, zinc (a competitor of iron), duodenal cytochrome b (DcytB) antibody neutralization and citrate
Vivek Barve et al.
Journal of medicinal chemistry, 49(13), 3800-3808 (2006-06-23)
The synthesis and characterization of Schiff base derivatives of 3-formylchromone 3-6 (FPA-120 to FPA-123), the minimal biologically active structural motif of soy isoflavone, genistein, and their copper(II) complexes 7-10 (FPA-124 to FPA-127) are reported here. These copper complexes possess distorted
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