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G6649

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

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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
Quality level:
200
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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)

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

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.
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.

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

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD2501V
SLCD2548
SLCB9234
SLBW0900
SLBS6603

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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)
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