Glabrene

Glabrene
Names
IUPAC name
6′′,6′′-Dimethyl-6′′H-pyrano[2′′,3′′:2′,3′]isoflav-3-ene-4′,7-diol
Systematic IUPAC name
2′,2′-Dimethyl-2H,2′H-[3,8′-bi-1-benzopyran]-5′,7-diol
Other names
2',2'-dimethyl-2H,2'H-3,8'-bichromene-5',7-diol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C20H18O4/c1-20(2)8-7-16-17(22)6-5-15(19(16)24-20)13-9-12-3-4-14(21)10-18(12)23-11-13/h3-10,21-22H,11H2,1-2H3
    Key: NGGYSPUAKQMTNP-UHFFFAOYSA-N
  • CC1(C=CC2=C(C=CC(=C2O1)C3=CC4=C(C=C(C=C4)O)OC3)O)C
Properties
C20H18O4
Molar mass 322.36 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Glabrene is an isoflavonoid that is found in Glycyrrhiza glabra (licorice). It has estrogenic activity, showing estrogenic effects on breast, vascular, and bone tissue, and hence is a phytoestrogen (IC50 for estrogen receptor binding = 1 μM). It has also been found to act as a tyrosinase inhibitor (IC50 = 3.5 μM) and to inhibit the formation of melanin in melanocytes, and for these reasons, has been suggested as a potential skin-lightening agent.

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