Glabrene

Glabrene is an isoflavonoid that is found in Glycyrrhiza glabra (licorice).^[1] 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).^[1]^[2]^[3] It has also been found to act as a tyrosinase inhibitor (IC₅₀ = 3.5 μM) and to inhibit the formation of melanininmelanocytes, and for these reasons, has been suggested as a potential skin-lightening agent.^[4]

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
CAS Number	60008-03-9
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL462722
ChemSpider	421858
PubChem CID	480774
UNII	C6Y321Q75O
CompTox Dashboard (EPA)	DTXSID90208715
InChI 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
SMILES CC1(C=CC2=C(C=CC(=C2O1)C3=CC4=C(C=C(C=C4)O)OC3)O)C
Properties
Chemical formula	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

References

^ ^a ^b Tamir S, Eizenberg M, Somjen D, Izrael S, Vaya J (2001). "Estrogen-like activity of glabrene and other constituents isolated from licorice root". J. Steroid Biochem. Mol. Biol. 78 (3): 291–8. doi:10.1016/s0960-0760(01)00093-0. PMID 11595510. S2CID 40171833.

^ Somjen D, Knoll E, Vaya J, Stern N, Tamir S (2004). "Estrogen-like activity of licorice root constituents: glabridin and glabrene, in vascular tissues in vitro and in vivo". J. Steroid Biochem. Mol. Biol. 91 (3): 147–55. doi:10.1016/j.jsbmb.2004.04.003. PMID 15276622. S2CID 41966251.

^ Somjen D, Katzburg S, Vaya J, Kaye AM, Hendel D, Posner GH, Tamir S (2004). "Estrogenic activity of glabridin and glabrene from licorice roots on human osteoblasts and prepubertal rat skeletal tissues". J. Steroid Biochem. Mol. Biol. 91 (4–5): 241–6. doi:10.1016/j.jsbmb.2004.04.008. PMID 15336701. S2CID 16238533.

^ Nerya O, Vaya J, Musa R, Izrael S, Ben-Arie R, Tamir S (2003). "Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots". J. Agric. Food Chem. 51 (5): 1201–7. doi:10.1021/jf020935u. PMID 12590456.

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Glabrene

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