Glycitein - Misplaced Pages

Not to be confused with glycitin.

Glycitein
Names


IUPAC name 4′,7-Dihydroxy-6-methoxyisoflavone
Systematic IUPAC name 7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one
Identifiers
CAS Number	40957-83-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34778
ChEMBL	ChEMBL513024
ChemSpider	4476508
KEGG	C14536
PubChem CID	5317750
UNII	92M5F28TVF
CompTox Dashboard (EPA)	DTXSID40193960
InChI 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,1H3Key: DXYUAIFZCFRPTH-UHFFFAOYSA-N InChI=1/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,1H3Key: DXYUAIFZCFRPTH-UHFFFAOYAM
SMILES COC1=C(C=C2C(=C1)C(=O)C(=CO2)C3=CC=C(C=C3)O)O
Properties
Chemical formula	C₁₆H₁₂O₅
Molar mass	284.267 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Glycitein is an O-methylated isoflavone which accounts for 5-10% of the total isoflavones in soy food products. Glycitein is a phytoestrogen with weak estrogenic activity, comparable to that of the other soy isoflavones.

Glycitin (glycitein 7-O-glucoside) can be transformed to glycetein by human intestinal flora.

References

Song TT, Hendrich S, Murphy PA (1999). "Estrogenic activity of glycitein, a soy isoflavone". J. Agric. Food Chem. 47 (4): 1607–1610. Bibcode:1999JAFC...47.1607S. doi:10.1021/jf981054j. PMID 10564025. S2CID 22293253.

v t e Isoflavones and their glycosides
Isoflavones	Daidzein Genistein Orobol
O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin
Glycosides	Daidzin Genistin Iridin Mirificin Ononin Puerarin Sophoricoside Tectoridin
Prenylated isoflavones	Bidwillol A Derrubone Luteone 7-O-Methylluteone Wighteone
Pyranoisoflavones	Alpinumisoflavone Barbigerone Di-O-methylalpinumisoflavone 4'-methyl-alpinumisoflavone
Derivatives	Anagyroidisoflavone A and B Irilone Pseudobaptigenin Rotenoids
Synthetic	Ipriflavone

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