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Merck

G6776

Genistein

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :
C15H10O5
Numéro CAS:
446-72-0
Poids moléculaire :
270.24
NACRES:
NA.77
PubChem Substance ID:
24895273
UNSPSC Code:
12352200
EC Number:
207-174-9
MDL number:
MFCD00016952
Beilstein/REAXYS Number:
263823

Nom du produit

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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Catégories apparentées

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

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
0000486021
0000486021
0000458669
0000458669
0000404420

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Kazuki Kusuyama et al.
The spine journal : official journal of the North American Spine Society, 18(6), 1062-1069 (2018-01-23)
Spinal cord injury (SCI) commonly results not only in motor paralysis but also in the emergence of neuropathic pain (NeuP), both of which can impair the quality of life for patients with SCI. In the clinical field, it is well
Jessica N Peoples et al.
Biochemical and biophysical research communications, 495(4), 2547-2552 (2017-12-31)
Mouse embryos that lack the ability to produce the adrenergic hormones, norepinephrine (NE) and epinephrine (EPI), due to disruption of the dopamine beta-hydroxylase (Dbh-/-) gene inevitably perish from heart failure during mid-gestation. Since adrenergic stimulation is well-known to enhance calcium
Lin Yang et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 25(3), 928-936 (2010-12-04)
The cardiac voltage-gated Ca(2+) channel, Ca(v)1.2, mediates excitation-contraction coupling in the heart. The molecular composition of the channel includes the pore-forming α1 subunit and auxiliary α2/δ-1 and β subunits. Ca(2+) channel γ subunits, of which there are 8 isoforms, consist
Haolong Li et al.
Oncotarget, 6(24), 20474-20484 (2015-05-27)
Although the new generation of androgen receptor (AR) antagonists like enzalutamide (ENZ) prolong survival of metastatic castration-resistant prostate cancer (CRPC), AR-driven tumors eventually recur indicating that additional therapies are required to fully block AR function. Since DNA topoisomerase II (Topo
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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