Glycitein

Glycitein
Glycitein molecule
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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:34778 ☒N
ChEMBL
  • ChEMBL513024 ☒N
ChemSpider
  • 4476508 ☒N
KEGG
  • C14536 checkY
PubChem CID
  • 5317750
UNII
  • 92M5F28TVF checkY
CompTox Dashboard (EPA)
  • DTXSID40193960 Edit this at Wikidata
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,1H3 ☒N
    Key: DXYUAIFZCFRPTH-UHFFFAOYSA-N ☒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,1H3
    Key: DXYUAIFZCFRPTH-UHFFFAOYAM
  • 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−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1]

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

References

  1. ^ Song TT, Hendrich S, Murphy PA (1999). "Estrogenic activity of glycitein, a soy isoflavone". J. Agric. Food Chem. 47 (4): 1607–1610. doi:10.1021/jf981054j. PMID 10564025. S2CID 22293253.
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Isoflavones and their glycosides
IsoflavonesO-methylated isoflavonesGlycosidesPrenylated isoflavones
Pyranoisoflavones
Derivatives
Synthetic


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