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G6649

Sigma-Aldrich

Genistein

≥98% (HPLC), powder, tyrosine protein kinase inhibitor

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C15H10O5
Numéro CAS:
Poids moléculaire :
270.24
Numéro Beilstein :
263823
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

product name

Genistein, synthetic, ≥98% (HPLC), powder

Source biologique

synthetic

Niveau de qualité

Pureté

≥98% (HPLC)

Forme

powder

Couleur

off-white to yellow

Pf

297.0-298.0 °C

Solubilité

DMSO: soluble
ethanol: soluble

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

TZBJGXHYKVUXJN-UHFFFAOYSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Notes préparatoires

Genistein is soluble in DMSO and ethanol. It is also soluble in chlorform:methanol (1:1 (v:v), 10 mg/ml).

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type N95 (US)


Certificats d'analyse (COA)

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Les clients ont également consulté

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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)
Assaying estrogenicity by quantitating the expression levels of endogenous estrogen-regulated genes.
Jorgensen M, et al.
Environmental Health Perspectives, 108(5), 403-403 (2000)
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Oncotarget, 6(24), 20474-20484 (2015-05-27)
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