Glycitein

Glycitein Basic information
Product Name:Glycitein
Synonyms:GLYCETEIN;GLYCITEIN;4',7-DIHYDROXY-6-METHOXYISOFLAVONE;4,7-DIHYDROXY-6-METHOXYISOFLAVONE;7,4'-DIHYDROXY-6-METHOXYISOFLAVONE; Glicetein;7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one;4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-
CAS:40957-83-3
MF:C16H12O5
MW:284.26
EINECS:
Product Categories:Intermediates & Fine Chemicals;Pharmaceuticals;The group of Daidzin;chemical reagent;pharmaceutical intermediate;inhibitor;Iso-Flavones;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
Mol File:40957-83-3.mol
Glycitein Structure
Glycitein Chemical Properties
Melting point >300°C
Boiling point 547.4±50.0 °C(Predicted)
density 1.420±0.06 g/cm3(Predicted)
storage temp. -20°C
solubility Aqueous Base (Slightly), DMSO (Slightly)
form Solid
pka7.03±0.20(Predicted)
color Light Brown
InChIKeyDXYUAIFZCFRPTH-UHFFFAOYSA-N
LogP2.570 (est)
CAS DataBase Reference40957-83-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Safety Statements 24/25
WGK Germany 3
HS Code 29329990
MSDS Information
ProviderLanguage
SigmaAldrich English
Glycitein Usage And Synthesis
DescriptionGlycitein is an O-methylated isoflavone that comprises 5-10% of the total isoflavones in soy food products. This phytoestrogen is reported to have weak estrogenic activity, displacing estradiol binding at the estrogen receptor in vitro with an IC50 value of 3.94 μM. It suppresses the proliferation of osteoblasts and promotes differentiation from its progenitor. It has also been used to attenuate proliferation (10 μM) of aortic smooth muscle cells related to atherosclerotic vascular change in stroke-prone hypertensive rats and to protect against beta amyloid (Aβ)-induced toxicity and oxidative stress (100 μg/ml) in C. elegans expressing human Aβ.
Chemical PropertiesPale Orange Solid
UsesGlycitein may be used as a reference standard in the determination of glycitein in hydrolyzed dry soya extracts using reversed-phase high-performance liquid chromatography (RP-HPLC).
UsesGlycitein 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.
UsesThe compund shows an anti-cancer activity, plasma cholesterol reduction, reduction in postmenopausal bone loss
DefinitionChEBI: A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis.
General DescriptionGlycitein is an isoflavone found in soy food products.
Biochem/physiol ActionsGlycitein 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-7-O-METHYL ETHER Solvent Red 43 Emodin ICHTHYNONE Curcumin Riboflavin Riboflavin 5'-Monophosphate Sodium Salt 1-Hydroxyethylidene-1,1-diphosphonic acid Methoxydiethylborane Anisole (Trifluoromethoxy)benzene Theaflavin Triclosan p-Anisidine Glycitein Chrysin GLYCITEIN 7,4'-DIMETHYL ETHER Glycitin

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