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| Names | |
|---|---|
| IUPAC name 4′,7-Dihydroxy-6-methoxyisoflavone | |
| Systematic IUPAC name 7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| KEGG |
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| UNII | |
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| Properties | |
| C16H12O5 | |
| Molar mass | 284.267 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Glycitein is anO-methylated isoflavone which accounts for 5-10% of the total isoflavones insoy food products. Glycitein is aphytoestrogen with weak estrogenic activity, comparable to that of the other soy isoflavones.[1] Like other isoflavonoids, glycitein is synthesized as aglycoside conjugate to a monosaccharide (typicallyglucose). The glycoside is hydrolyzed during digestion to the biologically-active free isoflavonoid.[2]
Glycitein is synthesized fromphenylalanine, similarly to other isoflavonoids. The biosynthesis involves 8 steps, resulting in free glycitein; a subsequentglucosyltransferase-catalyzed reaction results in the corresponding glucoside,glycitin. This product may be further malonylated tomalonylglycitin.[3]
Glycitein has been investigated for its benefits to human health. It binds to the humanestrogen receptor (as do other isoflavonoids), and while it does so with lower affinity than other isoflavonoids, it is thought to be overall more potent as an estrogen receptor agonist due to its highbioavailability and its breakdown into further estrogenic products. The estrogenic activity of glycitein is thought to underlie its suppression ofoxidative stress and its promotion of decreasedblood pressure, though other mechanisms are likely also involved.[4]
Isoflavones and theirglycosides | |
|---|---|
| Isoflavones | |
| O-methylated isoflavones | |
| Glycosides | |
| Prenylated isoflavones | |
| Pyranoisoflavones | |
| Derivatives | |
| Synthetic | |
