glabrene

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| ImageFile = Glabrene.svg

| ImageSize = 250

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| IUPACName = 6′′,6′′-Dimethyl-6′′H-pyrano[2′′,3′′:2′,3′]isoflav-3-ene-4′,7-diol

| SystematicName = 2′,2′-Dimethyl-2H,2′H-[3,8′-bi-1-benzopyran]-5′,7-diol

| OtherNames = 2',2'-dimethyl-2H,2'H-3,8'-bichromene-5',7-diol

| Section1 = {{Chembox Identifiers

| CASNo = 60008-03-9

| ChEMBL = 462722

| ChemSpiderID = 421858

| PubChem = 480774

| StdInChI = 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

| StdInChIKey = NGGYSPUAKQMTNP-UHFFFAOYSA-N

| SMILES = CC1(C=CC2=C(C=CC(=C2O1)C3=CC4=C(C=C(C=C4)O)OC3)O)C

| UNII = C6Y321Q75O

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| Section2 = {{Chembox Properties

| C=20 | H=18 | O=4

| MolarMass = 322.36 g/mol

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| Section3 = {{Chembox Hazards

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Glabrene is an isoflavonoid that is found in Glycyrrhiza glabra (licorice).{{cite journal | vauthors = Tamir S, Eizenberg M, Somjen D, Izrael S, Vaya J | title = Estrogen-like activity of glabrene and other constituents isolated from licorice root | journal = J. Steroid Biochem. Mol. Biol. | volume = 78 | issue = 3 | pages = 291–8 | year = 2001 | pmid = 11595510 | doi = 10.1016/s0960-0760(01)00093-0| s2cid = 40171833 }} 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).{{cite journal | vauthors = Somjen D, Knoll E, Vaya J, Stern N, Tamir S | title = Estrogen-like activity of licorice root constituents: glabridin and glabrene, in vascular tissues in vitro and in vivo | journal = J. Steroid Biochem. Mol. Biol. | volume = 91 | issue = 3 | pages = 147–55 | year = 2004 | pmid = 15276622 | doi = 10.1016/j.jsbmb.2004.04.003 | s2cid = 41966251 }}{{cite journal | vauthors = Somjen D, Katzburg S, Vaya J, Kaye AM, Hendel D, Posner GH, Tamir S | title = Estrogenic activity of glabridin and glabrene from licorice roots on human osteoblasts and prepubertal rat skeletal tissues | journal = J. Steroid Biochem. Mol. Biol. | volume = 91 | issue = 4–5 | pages = 241–6 | year = 2004 | pmid = 15336701 | doi = 10.1016/j.jsbmb.2004.04.008 | s2cid = 16238533 }} 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.{{cite journal | vauthors = Nerya O, Vaya J, Musa R, Izrael S, Ben-Arie R, Tamir S | title = Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots | journal = J. Agric. Food Chem. | volume = 51 | issue = 5 | pages = 1201–7 | year = 2003 | pmid = 12590456 | doi = 10.1021/jf020935u }}