CAS 59870-68-7|Glabridin
| Common Name | Glabridin | ||
|---|---|---|---|
| CAS Number | 59870-68-7 | Molecular Weight | 324.37 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 518.6±50.0 °C at 760 mmHg |
| Molecular Formula | C20H20O4 | Melting Point | 154-155ºC |
| MSDS | ChineseUSA | Flash Point | 267.4±30.1 °C |
Names
| Name | glabridin |
|---|---|
| Synonym | More Synonyms |
Glabridin BiologicalActivity
| Description | Glabridin is a natural isoflavan from Glycyrrhiza glabra, binds to and activates PPARγ, with an EC50 of 6115 nM. Glabridin exhibits antioxidant, anti-bacterial, anti-nephritic, anti-diabetic, anti-fungal, antitumor, anti-inflammatory, antiosteoporotic, cardiovascular protective, neuroprotective and radical scavenging activities[1][2]. |
|---|---|
| Related Catalog | Research Areas >>CancerSignaling Pathways >>Cell Cycle/DNA Damage >>PPARResearch Areas >>Inflammation/Immunology |
| Target | PPARγ:6.1 μM (EC50) |
| In Vitro | Glabridin binds to and activates PPARγ, with an EC50 of 6115 nM[1]. Glabridin (40, 80 μM) inhibits the proliferation of SCC-9 and SAS cell lines in a dose- and time-dependent manner after treatment for 24 and 48 h[2]. Glabridin (0-80 μM) also induces apoptosis, causes Sub-G1 cell cycle arrest in SCC-9 and SAS cell lines[2]. Glabridin (0, 20, 40, and 80 μM) dose-dependently activates caspase-3, −8, and −9 and increases PARP cleavage, significantly phosphorylates ERK1/2, JNK1/2, and p-38 MAPK in SCC-9 cells[2]. |
| In Vivo | Glabridin (50 mg/kg, p.o. once daily) shows potent anti-inflammatory activity, ameliorates the inflammatory alterations induced by Dextran sodium sulphate (DSS) in rats[3]. |
| References | [1]. Rebhun JF, et al. Identification of glabridin as a bioactive compound in licorice (Glycyrrhiza glabra L.) extract that activates human peroxisome proliferator-activated receptor gamma (PPARγ). Fitoterapia. 2015 Oct;106:55-61. [2]. Chen CT, et al. Glabridin induces apoptosis and cell cycle arrest in oral cancer cells through the JNK1/2 signaling pathway. Environ Toxicol. 2018 Jun;33(6):679-685. [3]. El-Ashmawy NE, et al. Downregulation of iNOS and elevation of cAMP mediate the anti-inflammatory effect of glabridin in rats with ulcerative colitis. Inflammopharmacology. 2018 Apr;26(2):551-559. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 518.6±50.0 °C at 760 mmHg |
| Melting Point | 154-155ºC |
| Molecular Formula | C20H20O4 |
| Molecular Weight | 324.37 |
| Flash Point | 267.4±30.1 °C |
| Exact Mass | 324.136169 |
| PSA | 58.92000 |
| LogP | 4.26 |
| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
| Index of Refraction | 1.623 |
| InChIKey | LBQIJVLKGVZRIW-ZDUSSCGKSA-N |
| SMILES | CC1(C)C=Cc2c(ccc3c2OCC(c2ccc(O)cc2O)C3)O1 |
| Storage condition | room temp |
Safety Information
| Hazard Statements | H413 |
|---|---|
| Hazard Codes | Xi |
| RIDADR | NONH for all modes of transport |
| HS Code | 2942000000 |
Customs
| HS Code | 2942000000 |
|---|
Articles31
More Articles| Glabridin inhibits migration and invasion by transcriptional inhibition of matrix metalloproteinase 9 through modulation of NF-κB and AP-1 activity in human liver cancer cells. Br. J. Pharmacol. 171(12) , 3037-50, (2014) High mortality and morbidity rates for hepatocellular carcinoma in Taiwan primarily result from uncontrolled tumour metastasis. Glabridin, a prenylated isoflavonoid of licorice (Glycyrrhiza glabra) ro... | |
| Novel phytonutrient contributors to antioxidant protection against cardiovascular disease Nutrition 28(6) , 605-10, (2012) The associations linking endothelial inflammation, endothelial oxidative stress, and atherogenesis and the potential for dietary phytonutrients to decrease the impact of these associations were assess... | |
| Glabridin inhibits migration, invasion, and angiogenesis of human non-small cell lung cancer A549 cells by inhibiting the FAK/rho signaling pathway. Integr. Cancer Ther. 10(4) , 341-9, (2011) This study reports the antimigration, anti-invasive effect of glabridin, a flavonoid obtained from licorice, in human non-small cell lung cancer A549 cells. Glabridin exhibited effective inhibition of... |
Synonyms
| 1,3-Benzenediol,4-(3,4-dihydro-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-3-yl)-,(R) |
| 4-(3,4-Dihydro-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-3-yl)-1,3-benzenediol |
| Glabridin |
| Bio-0904 |
| 4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol |
| 4-[(3R)-8,8-Dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol |
| BIDD:ER0172 |
| 4-[(3R)-8,8-Dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl]-1,3-benzenediol |
| 1,3-Benzenediol, 4-[(3R)-3,4-dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl]- |
| MFCD03427694 |
