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G6776 Sigma-Aldrich

Genistein

from Glycine max (soybean), ~98% (HPLC)

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

  • CAS Number 446-72-0

  • Empirical Formula (Hill Notation) C15H10O5

  • Molecular Weight 270.24

  •  Beilstein/REAXYS Number 263823

  •  EC Number 207-174-9

  •  MDL number MFCD00016952

  •  PubChem Substance ID 24895273

  •  NACRES NA.77

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Properties

Related Categories Angiogenesis, Angiogenesis Inhibitors, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
Quality Level   200
biological source   Glycine max (soybean)
assay   ~98% (HPLC)
form   powder
mp   > 280  °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 a nutraceutical isoflavnoid from soybean and is a phytoestrogen. It is derived from genistin.

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

Packaging

5, 10 mg in glass bottle

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
NR2392000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

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.1 During the oxi...
Biofiles Volume 2 Article 2
Keywords: Adhesion, Anti-inflammatory agents, Applications, Cancer, Cardiovascular, Catalysis, Diabetes, Diseases, Gene expression, Metabolism, Neurodegenerative Diseases, Peroxidations, Phosphorylations, Prebiotics, Probiotics, Reductions, Transcription, Transduction, Vitamins

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. Oxidative cellular ...
BioFiles 2007, 2.4, 14.
Keywords: Acetylations, Adhesion, Angiogenesis, Apoptosis, Cancer, Carcinogens, Catalysis, Cell culture, Cell proliferation, Cell signaling, Cellular processes, Degradations, Diabetes, Diseases, Environmental, Gene expression, Glycosylations, High performance liquid chromatography, Inflammation, PAGE, Phosphorylations, Thin layer chromatography, Transcription, transformation

Peer-Reviewed Papers
15

References

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