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G2785

Sigma-Aldrich

Glycitein

≥97% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H12O5
CAS Number:
40957-83-3
Molecular Weight:
284.26
MDL number:
MFCD00016679
UNSPSC Code:
41106305
PubChem Substance ID:
329799906
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

100

assay

≥97% (HPLC)

form

powder

solubility

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

storage temp.

−20°C

SMILES string

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

InChI key

DXYUAIFZCFRPTH-UHFFFAOYSA-N

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Application

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.

Biochem/physiol Actions

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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)
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