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G6776

Sigma-Aldrich

Genistein

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

Synonym(e):

4′,5,7-Trihydroxy-isoflavon, 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-on

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About This Item

Empirische Formel (Hill-System):
C15H10O5
CAS-Nummer:
446-72-0
Molekulargewicht:
270.24
Beilstein:
263823
EG-Nummer:
207-174-9
MDL-Nummer:
MFCD00016952
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24895273
NACRES:
NA.77

Biologische Quelle

Glycine max (soybean)

Qualitätsniveau

200

Assay

~98% (HPLC)

Form

powder

mp (Schmelzpunkt)

>280 °C

Löslichkeit

DMSO: soluble
ethanol: soluble

Lagertemp.

−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

InChIKey

TZBJGXHYKVUXJN-UHFFFAOYSA-N

Angaben zum Gen

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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Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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.

Leistungsmerkmale und Vorteile

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

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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16587

Daidzein

Glycitin ≥98% (HPLC)

Sigma-Aldrich

G1296

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Glycitein ≥97% (HPLC)

Sigma-Aldrich

G2785

Glycitein

Glycitein analytical standard

Supelco

43534

Glycitein

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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