4-[(3R)-8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol

• ChemBase ID: 127561
• Molecular Formular: C20H20O4
• Molecular Mass: 324.3704
• Monoisotopic Mass: 324.13615912
• SMILES: O1c2c3C=CC(Oc3ccc2C[C@H](c2ccc(O)cc2O)C1)(C)C
• Canonical SMILES: Oc1ccc(c(c1)O)[C@@H]1COc2c(C1)ccc1c2C=CC(O1)(C)C
• 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: LBQIJVLKGVZRIW-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(3R)-8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol; 4-[(5R)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^2,^7]tetradeca-1,7,9,13-tetraen-5-yl]benzene-1,3-diol
• IUPAC Traditional name: glabridin; 4-[(5R)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^2,^7]tetradeca-1,7,9,13-tetraen-5-yl]benzene-1,3-diol
• Synonyms: 4-[3,4-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl]-1,3-benzenediol; 4-[(3R)-3,4-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-3-yl]-1,3-benzenediol; (R)-4-(3,4-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-3-yl)-1,3-benzenediol; Glabridin; Glabridin; Glabridin

Database IDs

• CAS Number: 59870-68-7
• MDL Number: MFCD03427694
• Beilstein Number: 7141956
• PubChem SID: 162221880
• PubChem CID: 124052
• CHEMBL: 480477
• Chemspider ID: 110560
• Wikipedia Title: Glabridin

CALCULATED PROPERTIES

• Acid pKa: 9.516527
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.09226
• LogD (pH = 7.4): 4.0890117
• Log P: 4.0923014
• Molar Refractivity: 93.3536 cm^3
• Polarizability: 35.4321 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥14 mg/mL
• Apperance: white to tan powder; Yellowish-brown powder
• Melting Point: 156 - 158°C
• Flash Point: 267 °C; 512.6 °F

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413
• Storage Temperature: room temp

Pharmacology Properties

• Mechanism of Action: Human cytochrome P450S 3A4, 2B6, 2C9 inhibitor; Melanogenesis inhibitor; Tyrosinase inhibitor

Product Information

• Purity: ≥98% (HPLC); ≥98.0% (HPLC)
• Grade: analytical standard
• Biological Source: Isol. from Glycyrrhiza glabra
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Anti-inflammatory; Antimicrobial; Anti-proliferative; Cytotoxic; Estrogenic
• Empirical Formula (Hill Notation): C20H20O4

DETAILS

Sigma Aldrich - G9548

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.

REFERENCES

• 1. T. Fukai, H. Sakagami, M. Toguchi, F. Takayama, I. Iwakura and T. Atsumi, Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines,
• Anticancer Res 20 (2000), pp. 2525?536.
• 2. T. Fukai, A. Marumo, K. Kaitou, T. Kanda, S. Terada and T. Nomura, Anti-Helicobacter pylori flavonoids from licorice extract, Life Sci 71 (2002), pp. 1449?463
• 3. S. Tamir, M. Eizenberg, D. Somjen, S. Izrael and J. Vaya, Estrogen-like activity of glabrene and other constituents isolated from licorice root, J Steroid Biochem Mol Biol 78 (2001), pp. 291?98.
• 4. T. Yokota, H. Nishio, Y. Kubota and M. Mizoguchi, The inhibitory effect of glabridin from licorice extracts on melanogenesis and inflammation, Pigment Cell Res 11 (1998), pp. 355?61.
• 5. O. Nerya, J. Vaya, R. Musa, S. Izrael, R. Ben-Arie and S. Tamir, Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots, J Agric Food Chem 51 (2003), pp. 1201?207.
• 6. U.M. Kent, M. Aviram, M. Rosenblat and P.F. Hollenberg, The licorice root derived isoflavan glabridin inhibits the activities of human cytochrome P450S 3A4, 2B6, and 2C9,
• Drug Metab Dispos 30 (2002), pp. 709?15.
• 7. Choi, E. The licorice root derived isoflavan glabridin increases the function of osteoblastic
• MC3T3-E1 cells. Biochem. Pharm. 2005, 70, 363-368.