G6649 Sigma-Aldrich


synthetic, ≥98% (HPLC), powder

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 24278036

  •  NACRES NA.77



Related Categories Angiogenesis, Angiogenesis Inhibitors, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
Quality Level   200
biological source   synthetic
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
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)


General description

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


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


25, 100 mg in poly bottle

5 mg in glass bottle

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

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G6649.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

GHS07  GHS07
Signal word 
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles


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Keywords: Adhesion, Anti-inflammatory agents, Applications, Cancer, Cardiovascular, Catalysis, Diabetes, Diseases, Gene expression, Metabolism, Neurodegenerative Diseases, Peroxidations, Phosphorylations, Prebiotics, Probiotics, Reductions, Transcription, Transduction, Vitamins

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

Phosphorylation is a ubiquitous cellular regulatory mechanism that mediates signal transduction pathways, which carry signals from the cell surface to the nucleus or cytoplasm, by altering the activi...
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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

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