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G6649

Sigma-Aldrich

Genistein

synthetic, ≥98% (HPLC), powder

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Synonym(s):
4′,5,7-Trihydroxyisoflavone, 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Empirical Formula (Hill Notation):
C15H10O5
CAS Number:
Molecular Weight:
270.24
Beilstein/REAXYS Number:
263823
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

Quality Level

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

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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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)


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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)
Cloning of oestrogen receptor beta from Old and New World primates: identification of splice variants and functional analysis
Sierens JE, et al.
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Assaying estrogenicity by quantitating the expression levels of endogenous estrogen-regulated genes.
Jorgensen M, et al.
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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

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