G6776

Genistein

Name: Genistein
Brand: SIGMA

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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All Photos(2)

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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

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

0000458669

0000404420

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Intact calcium signaling in adrenergic-deficient embryonic mouse hearts.

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

Upregulation of calcium channel alpha-2-delta-1 subunit in dorsal horn contributes to spinal cord injury-induced tactile allodynia.

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

Citric acid mediates the iron absorption from low molecular weight human milk fractions.

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

Synthesis, molecular characterization, and biological activity of novel synthetic derivatives of chromen-4-one in human cancer cells.

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

Cardiac L-type calcium channel (Cav1.2) associates with gamma subunits.

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

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