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Key Documents

G2785

Sigma-Aldrich

Glycitein

≥97% (HPLC)

Sinônimo(s):

4′,7-Dihydroxy-6-methoxyisoflavone, Glycetein

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About This Item

Fórmula empírica (Notação de Hill):
C16H12O5
Número CAS:
Peso molecular:
284.26
Número MDL:
Código UNSPSC:
41106305
ID de substância PubChem:
NACRES:
NA.51

fonte biológica

synthetic (organic)

Ensaio

≥97% (HPLC)

forma

powder

solubilidade

DMF: 1 mg/mL, clear, colorless to faintly yellow

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

COc1cc2C(=O)C(=COc2cc1O)c3ccc(O)cc3

InChI

1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

chave InChI

DXYUAIFZCFRPTH-UHFFFAOYSA-N

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Aplicação

Glycitein has been used as standard for the analysis of soy isoflavones and metabolites in urine. It has also been used to bind to recombinant estrogen and progesterone receptors to know the relative binding affinity (RBA) for detection of potential endocrine disruptors.

Ações bioquímicas/fisiológicas

Glycitein is a soybean (yellow cultivar) isoflavonoid; its natural glycosides are synergistic with genistein in inducing specific gene expression. Glycitein may be used to study anti-oxidation processes at the level of gene transcription where it increases the binding of transcription factors [nuclear factor-E2-related factor 2 (Nrf2) and c-Jun] to the antioxidant response element (ARE) on HO-1 and NQO1 promoters. Glycitein may be used in combination with other isoflavonoids such as genistein and daidzein to study apoptosis.
Glycitein possesses weak estrogenic activity than other soy isoflavones.

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, Gloves, type N95 (US)


Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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

Sigma-Aldrich

G6776

Genistein

Calycosin ≥98% (HPLC)

Sigma-Aldrich

B9938

Calycosin

Daidzin analytical standard

Supelco

42926

Daidzin

Biochanin A

Sigma-Aldrich

D2016

Biochanin A

Glicerol ACS reagent, ≥99.5%

Sigma-Aldrich

G7893

Glicerol

Andrean L Simons et al.
Journal of agricultural and food chemistry, 53(22), 8519-8525 (2005-10-27)
Gut microbial disappearance and metabolism of the soy isoflavone glycitein, 7,4'-dihydroxy-6-methoxyisoflavone, were investigated by incubating glycitein anaerobically with feces from 12 human subjects. The subjects' ages ranged from 24 to 53 years with a body mass index (BMI) of 20.9-25.8
Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors
Scippo M L, et al.
Analytical and Bioanalytical Chemistry, 378(3), 664-669 (2004)
G Smit et al.
The Journal of biological chemistry, 267(1), 310-318 (1992-01-05)
Besides genistein and daidzein, which are active inducers of the nodYABCSUIJ operon in Bradyrhizobium japonicum, soybean seeds also excrete compounds that are not inducers of the nodYABCSUIJ genes but enhance induction of this operon in the presence of a suboptimal
Soy isoflavone metabolism in cats compared with other species: urinary metabolite concentrations and glucuronidation by liver microsomes
Redmon J M, et al.
Xenobiotica, 46(5), 406-415 (2016)
Estrogenic activity of glycitein, a soy isoflavone
Song T T, et al.
Journal of Agricultural and Food Chemistry, 47(4), 1607-1610 (1999)

Artigos

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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