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Glabridin

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Glabridin
Names
IUPAC name (3R)-6′′,6′′-Dimethyl-6′′H-pyranoisoflavan-2′,4′-diol
Systematic IUPAC name 4-dipyran)-3-yl]benzene-1,3-diol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.126.141 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1Key: LBQIJVLKGVZRIW-ZDUSSCGKSA-N
  • InChI=1/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1Key: LBQIJVLKGVZRIW-ZDUSSCGKBA
SMILES
  • O4c2c1\C=C/C(Oc1ccc2C(c3ccc(O)cc3O)C4)(C)C
Properties
Chemical formula C20H20O4
Molar mass 324.376 g·mol
Appearance Yellowish-brown powder
Melting point 238–240 °C (460–464 °F; 511–513 K)
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

Glabridin is a chemical compound that is found in the root extract of licorice (Glycyrrhiza glabra). Glabridin is an isoflavane, a type of isoflavonoid. This product is part of a larger family of plant-derived molecules, the natural phenols. Glabridin effectively inhibits platelet activation, so it might become therapeutic agent for thromboembolic disorders.

It is used as an ingredient in cosmetics and is listed in International Nomenclature of Cosmetic Ingredients (INCI).

Glabridin is yellowish-brown powder. It is insoluble in water, but soluble in organic solvents such as propylene glycol.

See also

References

  1. SciFinder Record for CAS#59870-68-7
  2. Kinoshita T, Kajiyama K, Hiraga Y, Takahashi K, Tamura Y, Mizutani K (1996). "Isoflavan derivatives from Glycyrrhiza glabra (licorice)". Heterocycles. 43 (3): 581–588.
  3. Chung CL, Chen JH, Huang WC, Sheu JR, Hsia CW, Jayakumar T, Hsia CH, Chiou KR, Hou SM (September 2022). "Glabridin, a Bioactive Flavonoid from Licorice, Effectively Inhibits Platelet Activation in Humans and Mice". International Journal of Molecular Sciences. 23 (19): 11372. doi:10.3390/ijms231911372. PMC 9570097. PMID 36232674. This article incorporates text from this source, which is available under the CC BY 4.0 license.
Isoflavanes
Isoflavanes:
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