| Identification | More | [Name]
Glabridin | [CAS]
59870-68-7 | [Synonyms]
GLABRIDIN
4-[(3R)-8,8-Dimethyl-3,4-dihydro-2H-pyrano[6,5-f]chromen-3-yl]benzene-1,3-diol
GLABRIDIN (GLYCYRRHIZA GLABRA ROOT EXTRACT) | [EINECS(EC#)]
611-908-7 | [Molecular Formula]
C20H20O4 | [MDL Number]
MFCD03427694 | [Molecular Weight]
324.37 | [MOL File]
59870-68-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
154～155℃ | [Boiling point ]
518.6±50.0 °C(Predicted) | [density ]
1.257±0.06 g/cm3(Predicted) | [Fp ]
267℃ | [storage temp. ]
room temp | [solubility ]
DMSO: soluble5mg/mL, clear (warmed) | [form ]
powder | [pka]
9.66±0.40(Predicted) | [color ]
white to light brown | [BRN ]
7141956 | [Stability:]
Hygroscopic | [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/s1 | [InChIKey]
PMPYOYXFIHXBJI-ZDUSSCGKSA-N | [SMILES]
C1(O)=CC=C([C@@H]2COC3=C4C=CC(C)(C)OC4=CC=C3C2)C(O)=C1 | [LogP]
4.260 (est) | [CAS DataBase Reference]
59870-68-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White to tan powder | [Uses]
Glabridin is a compound extracted from Licorice (root) shows properties that are cytotoxic, antimicrobial, estrogenic and anti-proliferative. | [Definition]
ChEBI: A member of the class of hydroxyisoflavans that is (R)-isoflavan substituted by hydroxy groups at positions 2' and 4' and a 2,2-dimethyl-2H-pyran group across positions 7 and 8 respectively. | [benefits]
Glabridin has strong antibacterial effects and can prevent inflammation, pigmentation, and rough skin caused by ultraviolet rays. It can also remove superoxide ions and inhibit hemolysis caused by hydrogen peroxide. Moreover, it can inhibit the activity of tyrosinase and the conversion of dopachrome, making it an effective and environmentally-friendly additive for whitening and freckle removal in cosmetics. Additionally, Glabridin possesses similar abilities to scavenge oxygen free radicals as SOD (superoxide dismutase) and vitamin E, making it a powerful antioxidant. | [Biochem/physiol Actions]
Glabridin is a bio-available isoflavan isolated from licorice (Glycyrrhiza glabra L.) root extract. Glabridin has been reported to posses varies biological activities including strong antioxidant activity, antioxidant against LDL oxidation, anti-Helicobacter pylori properties, estrogen-like activity and antinephritic and radical scavenging activities. Also it appears to inhibit serotonin re-uptake, melanogenesis, inflammation and cytochrome P450 3A4, 2B6, and 2C9. | [Mode of action]
Glabridin[59870-68-7] is one of the main flavonoid components in Glycyrrhiza glabra. It shows a strong anti-free radical oxidation effect in the cytochrome P450/NADPH oxidation system, which can significantly inhibit the free radicals produced in the metabolic process of the body, to avoid oxidative damage to oxidation-sensitive biological macromolecules (low-density lipoprotein LDL, DNA) and the cell wall, etc. by free radical oxidation. Thus, it can prevent certain pathological changes related to free radical oxidation, such as atherosclerosis, and cellular aging. In addition, Glabridin has some hypolipidemic and hypotensive effects. | [References]
Glabridin, a functional compound of liquorice, attenuates colonic inflammation in mice with dextran sulphate sodium‐induced colitis DOI:10.1111/j.1365-2249.2007.03539.x
Structural insights into the binding behavior of isoflavonoid glabridin with human serum albumin DOI:10.1016/J.FOODHYD.2019.01.031
A novel ?uorescent recombinant cell-based biosensor for screening NLRP3 inflammasome inhibitors DOI:10.1016/j.snb.2019.126864
Glavonoid, a possible supplement for prevention of ATTR amyloidosis DOI:10.1016/j.heliyon.2021.e08101
Tian, M. et al.: Int. J. Mol. Sci., 9, 571 (2008); Simmler, C. et al.: Fitoterapia, 90, 160 (2013); |
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