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Merck
CN

G2785

Glycitein

≥97% (HPLC), synthetic (organic), powder

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
UNSPSC Code:
41106305
PubChem Substance ID:
329799906
NACRES:
NA.51
MDL number:
MFCD00016679
Assay:
≥97% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
DMF: 1 mg/mL, clear, colorless to faintly yellow
Storage temp.:
−20°C

Key Documents

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Product Name

Glycitein, ≥97% (HPLC)

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 possesses weak estrogenic activity than other soy isoflavones.
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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV1065
MKCS1029
MKCQ1733
MKCM1405
MKCH0417

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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
Jin-Sun Park et al.
Journal of neurochemistry, 119(5), 909-919 (2011-07-26)
The brain is highly vulnerable to oxidative stress, thus controlling oxidative stress is considered to be an important therapeutic target for neurodegenerative diseases. In this study, we found that two isoflavone metabolites (tectorigenin and glycitein) inhibited hydrogen peroxide-induced reactive oxygen
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)
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
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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Articles

Dietary Antioxidants

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.

膳食抗氧化剂

抗氧化剂可保护生物系统免受含氧自由基和氧化还原过渡金属离子（如铁、铜和镉）引起的氧化损伤。

Global Trade Item Number

SKUGTIN
G2785-10MG04061833629444

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