Glabridin

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Glabridin
Glabridin.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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 Yes check.svgY
    Key: LBQIJVLKGVZRIW-ZDUSSCGKSA-N Yes check.svgY
  • 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
AppearanceYellowish-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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Related Research Articles

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<span class="mw-page-title-main">Liquorice (confectionery)</span> Type of confection or sweet food

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<span class="mw-page-title-main">Licochalcone A</span> Chemical compound

Licochalcone A is a chalconoid, a type of natural phenol. It can be isolated from the root of Glycyrrhiza glabra (liquorice) or Glycyrrhiza inflata. It shows antimalarial, anticancer, antibacterial and antiviral properties in vitro.

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<span class="mw-page-title-main">Glabrene</span> Chemical compound

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.

Antiandrogens in the environment have become a topic of concern. Many industrial chemicals, including phthalates and pesticides, exhibit antiandrogen activity in animal experiments. Certain plant species have also been found to produce antiandrogens. In animal studies, environmental antiandrogens can harm reproductive organ development in fetuses exposed in utero as well as their offspring.

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.