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G6776

Sigma-Aldrich

Genistein

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

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
Beilstein:
263823
EC Number:
207-174-9
MDL number:
MFCD00016952
UNSPSC Code:
12352200
PubChem Substance ID:
24895273
NACRES:
NA.77

biological source

Glycine max (soybean)

Quality Level

200

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)

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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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

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’.

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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
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