Skip to Content
Merck
CN
All Photos(4)

Documents

G6649

Sigma-Aldrich

Genistein

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

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(4)

About This Item

Empirical Formula (Hill Notation):
C15H10O5
CAS Number:
446-72-0
Molecular Weight:
270.24
Beilstein:
263823
EC Number:
207-174-9
MDL number:
MFCD00016952
UNSPSC Code:
12352200
PubChem Substance ID:
24278036
NACRES:
NA.77

product name

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

biological source

synthetic

Quality Level

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)

Looking for similar products? Visit Product Comparison Guide

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Cloning of oestrogen receptor beta from Old and New World primates: identification of splice variants and functional analysis
Sierens JE, et al.
Journal of Molecular Endocrinology, 32(3), 703-718 (2004)
Genistein
Dixon RA and Ferreira D
Phytochemistry, 60(3), 205-211 (2002)
Autophagy-lysosome pathway in renal tubular epithelial cells is disrupted by advanced glycation end products in diabetic nephropathy
Liu WJ, et al.
Test, jbc-M115 (2015)
Assaying estrogenicity by quantitating the expression levels of endogenous estrogen-regulated genes.
Jorgensen M, et al.
Environmental Health Perspectives, 108(5), 403-403 (2000)
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
View All Related Papers

Articles

NF-κB and Inflammation

Chronic inflammation is an underlying factor in the development and progression of many of the chronic diseases of aging, such as arthritis, atherosclerosis, diabetes, and cancer.

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service