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G6776

Sigma-Aldrich

Genistein

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

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C15H10O5
Número CAS:
446-72-0
Peso molecular:
270.24
Beilstein:
263823
Número CE:
207-174-9
Número MDL:
MFCD00016952
Código UNSPSC:
12352200
ID de substância PubChem:
24895273
NACRES:
NA.77

fonte biológica

Glycine max (soybean)

Nível de qualidade

200

Ensaio

~98% (HPLC)

Formulário

powder

pf

>280 °C

solubilidade

DMSO: soluble
ethanol: soluble

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

TZBJGXHYKVUXJN-UHFFFAOYSA-N

Informações sobre genes

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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Descrição geral

Genistein is a nutraceutical isoflavnoid from soybean and is a phytoestrogen. It is derived from genistin.

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Características e benefícios

This compound is featured on the Met page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302

Declarações de precaução

P264 - P270 - P301 + P312 - P501

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificados de análise (COA)

Lot/Batch Number
128M4027V
12180763
058M4105V
058M4015V
067M4165V

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Supelco

43534

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Calycosin ≥98% (HPLC)

Sigma-Aldrich

B9938

Calycosin

Haolong Li et al.
Oncotarget, 6(24), 20474-20484 (2015-05-27)
Although the new generation of androgen receptor (AR) antagonists like enzalutamide (ENZ) prolong survival of metastatic castration-resistant prostate cancer (CRPC), AR-driven tumors eventually recur indicating that additional therapies are required to fully block AR function. Since DNA topoisomerase II (Topo
Vivek Barve et al.
Journal of medicinal chemistry, 49(13), 3800-3808 (2006-06-23)
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
Darren M Hutt et al.
Nature chemical biology, 6(1), 25-33 (2009-12-08)
Chemical modulation of histone deacetylase (HDAC) activity by HDAC inhibitors (HDACi) is an increasingly important approach for modifying the etiology of human disease. Loss-of-function diseases arise as a consequence of protein misfolding and degradation, which lead to system failures. The
J W Lampe et al.
The American journal of clinical nutrition, 60(1), 122-128 (1994-07-01)
Lignans and isoflavonoid phytoestrogens, produced from plant precursors by colonic bacteria, may protect against certain cancers. We examined the effects of flaxseed consumption on urinary lignans and isoflavonoids. Eighteen women consumed their usual omnivorous diets for three menstrual cycles and
Selin Bolca et al.
The American journal of clinical nutrition, 91(4), 976-984 (2010-02-19)
Despite decades of research on the relation between soy and breast cancer, questions regarding the absorption, metabolism, and distribution of isoflavones in breast tissue largely remain unanswered. We evaluated the potential health effects of isoflavone consumption on normal breast tissue;
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