Glabridin

Glabridin
Names
IUPAC name
(3R)-6′′,6′′-Dimethyl-6′′H-pyrano[2′′,3′′:7,8]isoflavan-2′,4′-diol
Systematic IUPAC name
4-[(3R)-8,8-Dimethyl-3,4-dihydro-2H,8H-(benzo[1,2-b:3,4-b′]dipyran)-3-yl]benzene-1,3-diol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.126.141 Edit this at Wikidata
UNII
  • 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/s1 checkY
    Key: LBQIJVLKGVZRIW-ZDUSSCGKSA-N checkY
  • 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/s1
    Key: LBQIJVLKGVZRIW-ZDUSSCGKBA
  • O4c2c1\C=C/C(Oc1ccc2C[C@H](c3ccc(O)cc3O)C4)(C)C
Properties
C20H20O4
Molar mass 324.376 g·mol−1
Appearance Yellowish-brown powder
Melting point 238–240 °C (460–464 °F; 511–513 K)[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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Glabridin is a chemical compound that is found in the root extract of licorice (Glycyrrhiza glabra).[2] 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.[3]

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

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References

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  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.
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