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G6649

Genistein

Name: Genistein
Brand: SIGMA

≥98% (HPLC), powder, tyrosine protein kinase inhibitor

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:

24278036

UNSPSC Code:

12352200

EC Number:

207-174-9

MDL number:

MFCD00016952

Beilstein/REAXYS Number:

263823

Assay:

≥98% (HPLC)

Form:

powder

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Properties

Product Name

Genistein, synthetic, ≥98% (HPLC), powder

biological source

synthetic

Quality Segment

200

assay

≥98% (HPLC)

form

powder

color

off-white to yellow

mp

297.0-298.0 °C

solubility

DMSO: soluble, ethanol: soluble

storage temp.

−20°C

SMILES string

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

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

InChI key

TZBJGXHYKVUXJN-UHFFFAOYSA-N

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)

Description

General description

Genistein is an isoflavonoid present among Leguminosae family of plants. It is structurally similar to estrogen (estradiol-17β).

Application

Genistein has been used:

as a test compound to access its estrogeniic acivity
as an oestrogenic ligand to carry out identical reporter gene activation assays and also used to examine the binding of genistein to hERβ
as an endocytosis inhibitor to test the possible effect of endocytosed advanced glycation end - bovine serum albumin (AGE-BSA) on lysosomes

Biochem/physiol Actions

Genistein is essential for plant-microbe interaction. It acts as a natural chemoprotectant and helps in preventing tumor progression and heart disorders. Genistein functionally shares estrogen′s action. It is useful in evaluating nutraceuticals and functional foods. Genistein exhibits antimicrobial action and can serve as a phytoalexin and phytoanticipin.

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 a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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

Preparation Note

Genistein is soluble in DMSO and ethanol. It is also soluble in chlorform:methanol (1:1 (v:v), 10 mg/ml).

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Pictograms

GHS07

Signal Word

Warning

Hazard Codes

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

Flash Point (°F)

Not applicable

Flash Point (°C)