glabridin

4-(3,4-dihydro-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-3-yl)-1,3-benzenediol

CAS: 59870-68-7 C20 H20 O4 MW: 324.37620000

Identification

Nameglabridin
IUPAC4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol
CAS Number59870-68-7
FDA UNIIHOC5567T41
Molecular FormulaC20 H20 O4
Molecular Weight324.37620000
MDL NumberMFCD03427694
Nikkaji NumberJ649.087E
Beilstein7141956

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 518.60 °C. @ 760.00 mm Hg (est)
Flash Point 513.00 °F. TCC ( 267.40 °C. ) (est)
logP (o/w) 4.260 (est)
Soluble in water, 0.9288 mg/L @ 25 °C (est)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesbleaching agents

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for glabridin usage levels up tonot for fragrance use.
Recommendation for glabridin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

licorice

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 4-[(3R)-8,8- dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol PubMed: The use of enzyme-coupled magnetic nanoparticles for studying the spectra of unusual substrates of mushroom tyrosinase by direct surface-assisted laser desorption/ionisation and high-resolution electrospray ionisation quadrupole-quadrupole-time-of-flight mass spectrometry. PubMed: Synergistic antifungal effect of glabridin and fluconazole. PubMed: Effectively designed molecularly imprinted polymers for selective extraction of glabridin from Glycyrrhiza glabra L. residues by screening the library of non-imprinted polymers. PubMed: Glabridin induces glucose uptake via the AMP-activated protein kinase pathway in muscle cells. PubMed: Glabridin mediate caspases activation and induces apoptosis through JNK1/2 and p38 MAPK pathway in human promyelocytic leukemia cells. PubMed: The repressive effect of miR-148a on TGF beta-SMADs signal pathway is involved in the glabridin-induced inhibition of the cancer stem cells-like properties in hepatocellular carcinoma cells. PubMed: Glabridin attenuates the migratory and invasive capacity of breast cancer cells by activating microRNA-200c. PubMed: 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. PubMed: Enzyme-coupled nanoparticles-assisted laser desorption ionization mass spectrometry for searching for low-mass inhibitors of enzymes in complex mixtures. PubMed: Crystal structures of human transthyretin complexed with glabridin. PubMed: Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species. PubMed: Glabridin induces oxidative stress mediated apoptosis like cell death of malaria parasite Plasmodium falciparum. PubMed: Absolute configuration of naturally occurring glabridin. PubMed: Potentiating effect of glabridin on GABAA receptor-mediated responses in dorsal raphe neurons. PubMed: Phytochemistry and biological properties of glabridin. PubMed: The effects and mechanism of flavonoid-rePON1 interactions. Structure-activity relationship study. PubMed: Glabridin. PubMed: Hypoglycemic effects of glabridin, a polyphenolic flavonoid from licorice, in an animal model of diabetes mellitus. PubMed: In vitro anti-Helicobacter pylori activity of a flavonoid rich extract of Glycyrrhiza glabra and its probable mechanisms of action. PubMed: The flavonoid glabridin attenuates 2-deoxy-D-ribose-induced oxidative damage and cellular dysfunction in MC3T3-E1 osteoblastic cells. PubMed: Preparing glabridin-in-water nanoemulsions by high pressure homogenization with response surface methodology. PubMed: Anti-obesity effects of glabridin-rich supercritical carbon dioxide extract of licorice in high-fat-fed obese mice. PubMed: Rapid RP-HPLC method for the quantification of glabridin in crude drug and in polyherbal formulation. PubMed: AMPK activation with glabridin ameliorates adiposity and lipid dysregulation in obesity. PubMed: Novel phytonutrient contributors to antioxidant protection against cardiovascular disease. PubMed: Tyrosinase inhibitor-loaded microsponge drug delivery system: new approach for hyperpigmentation disorders. PubMed: Glabridin protects paraoxonase 1 from linoleic acid hydroperoxide inhibition via specific interaction: a fluorescence-quenching study. PubMed: The inhibitory effect and the molecular mechanism of glabridin on RANKL-induced osteoclastogenesis in RAW264.7 cells. PubMed: Licorice and its potential beneficial effects in common oro-dental diseases. PubMed: Mutual interaction of special phytoestrogenic compounds, their synthetic carboxy-derivatives and the less-calcemic vitamin D analog activities in human derived female cultured osteoblasts. PubMed: Traditional chinese medicine for senile dementia. PubMed: 18beta-glycyrrhetinic acid and glabridin prevent oxidative DNA fragmentation in UVB-irradiated human keratinocyte cultures. PubMed: Glabridin protects osteoblastic MC3T3-E1 cells against antimycin A induced cytotoxicity. PubMed: Glabridin as a major active isoflavan from Glycyrrhiza glabra (licorice) reverses learning and memory deficits in diabetic rats. PubMed: Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans. PubMed: Agonistic and antagonistic estrogens in licorice root (Glycyrrhiza glabra). PubMed: Modulation of lipopolysaccharide-induced pro-inflammatory mediators by an extract of Glycyrrhiza glabra and its phytoconstituents. PubMed: Factors influencing glabridin stability. PubMed: Natural products and body weight control. PubMed: Glabridin inhibits migration, invasion, and angiogenesis of human non-small cell lung cancer A549 cells by inhibiting the FAK/rho signaling pathway. PubMed: Glabridin, a phytoestrogen from licorice root, up-regulates manganese superoxide dismutase, catalase and paraoxonase 2 under glucose stress. PubMed: Dual inhibitory effect of Glycyrrhiza glabra (GutGard™) on COX and LOX products. PubMed: Inhibition of bone marrow-derived dendritic cell maturation by glabridin. PubMed: Glabridin, an isoflavan from licorice root, inhibits migration, invasion and angiogenesis of MDA-MB-231 human breast adenocarcinoma cells by inhibiting focal adhesion kinase/Rho signaling pathway. PubMed: Antidyslipidaemic activity of Glycyrrhiza glabra in high fructose diet induced dsyslipidaemic Syrian golden hamsters. PubMed: Antioxidant effect of polyphenolic glabridin on LDL oxidation. PubMed: A validated stability-indicating HPLC method for analysis of glabridin prodrugs in hydrolysis studies. PubMed: Synthesis of glabridin derivatives as tyrosinase inhibitors. PubMed: Glabridin inhibits lipopolysaccharide-induced activation of a microglial cell line, BV-2, by blocking NF-kappaB and AP-1. PubMed: Extraction of glycyrrhizic acid and glabridin from licorice. PubMed: Antifungal activity of Glycyrrhiza glabra extracts and its active constituent glabridin. PubMed: Glabridin from Chinese herb licorice inhibits fatigue in mice. PubMed: The effect of an endogenous antioxidant glabridin on oxidized LDL. PubMed: Effect of glabridin from Glycyrrhiza glabra on learning and memory in mice. PubMed: 90-Day repeated-dose toxicity study of licorice flavonoid oil (LFO) in rats. PubMed: Inhibition of P-glycoprotein and multidrug resistance protein 1 by dietary phytochemicals. PubMed: Antimicrobial potential of Glycyrrhiza glabra roots. PubMed: In vitro and in vivo neuroprotective effect and mechanisms of glabridin, a major active isoflavan from Glycyrrhiza glabra (licorice). PubMed: Glabridin, a functional compound of liquorice, attenuates colonic inflammation in mice with dextran sulphate sodium-induced colitis. PubMed: Absorption of dietary licorice isoflavan glabridin to blood circulation in rats. PubMed: Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update. PubMed: Clinical safety of licorice flavonoid oil (LFO) and pharmacokinetics of glabridin in healthy humans. PubMed: Constituent properties of licorices derived from Glycyrrhiza uralensis, G. glabra, or G. inflata identified by genetic information. PubMed: Role of P-glycoprotein in limiting the brain penetration of glabridin, an active isoflavan from the root of Glycyrrhiza glabra. PubMed: Anti-oxidant constituents of the roots and stolons of licorice (Glycyrrhiza glabra). PubMed: Role of P-glycoprotein in the intestinal absorption of glabridin, an active flavonoid from the root of Glycyrrhiza glabra. PubMed: Suppression by licorice flavonoids of abdominal fat accumulation and body weight gain in high-fat diet-induced obese C57BL/6J mice. PubMed: Post TLC developing technique for tyrosinase inhibitor detection. PubMed: Glabridin suppresses intercellular adhesion molecule-1 expression in tumor necrosis factor-alpha-stimulated human umbilical vein endothelial cells by blocking sphingosine kinase pathway: implications of Akt, extracellular signal-regulated kinase, and nuclear factor-kappaB/Rel signaling pathways. PubMed: Determination of glabridin in human plasma by solid-phase extraction and LC-MS/MS. PubMed: Identification of tyrosinase inhibitors from Glycyrrhiza uralensis. PubMed: Analysis and comparison of Radix Glycyrrhizae (licorice) from Europe and China by capillary-zone electrophoresis (CZE). PubMed: The licorice root derived isoflavan glabridin increases the function of osteoblastic MC3T3-E1 cells. PubMed: Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs. PubMed: Therapeutic drugs that behave as mechanism-based inhibitors of cytochrome P450 3A4. PubMed: Glabridin, an isoflavan from licorice root, inhibits inducible nitric-oxide synthase expression and improves survival of mice in experimental model of septic shock. PubMed: Licorice flavonoids suppress abdominal fat accumulation and increase in blood glucose level in obese diabetic KK-A(y) mice. PubMed: Estrogenic activity of glabridin and glabrene from licorice roots on human osteoblasts and prepubertal rat skeletal tissues. PubMed: Estrogen-like activity of licorice root constituents: glabridin and glabrene, in vascular tissues in vitro and in vivo. PubMed: Herbal bioactivation: the good, the bad and the ugly. PubMed: Antinephritis and radical scavenging activity of prenylflavonoids. PubMed: Preliminary evaluation of antinephritis and radical scavenging activities of glabridin from Glycyrrhiza glabra. PubMed: Field survey of Glycyrrhiza plants in Central Asia (3). Chemical characterization of G. glabra collected in Uzbekistan. PubMed: Evaluation of the antioxidant activity of different flavonoids by the chemiluminescence method. PubMed: Field survey of Glycyrrhiza plants in Central Asia (1). Characterization of G. uralensis, G. glabra and the putative intermediate collected in Kazakhstan. PubMed: Inhibition of serotonin re-uptake by licorice constituents. PubMed: Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots. PubMed: Anti-Helicobacter pylori flavonoids from licorice extract. PubMed: Increased macrophage glutathione content reduces cell-mediated oxidation of LDL and atherosclerosis in apolipoprotein E-deficient mice. PubMed: The licorice root derived isoflavan glabridin inhibits the activities of human cytochrome P450S 3A4, 2B6, and 2C9. PubMed: Oxidative stress increases the expression of the CD36 scavenger receptor and the cellular uptake of oxidized low-density lipoprotein in macrophages from atherosclerotic mice: protective role of antioxidants and of paraoxonase. PubMed: Estrogen-like activity of glabrene and other constituents isolated from licorice root. PubMed: Lycopene synergistically inhibits LDL oxidation in combination with vitamin E, glabridin, rosmarinic acid, carnosic acid, or garlic. PubMed: Estrogenic and antiproliferative properties of glabridin from licorice in human breast cancer cells. PubMed: Phenolic constituents of licorice. VIII. Structures of glicophenone and glicoisoflavanone, and effects of licorice phenolics on methicillin-resistant Staphylococcus aureus. PubMed: Protection of mitochondrial functions against oxidative stresses by isoflavans from Glycyrrhiza glabra. PubMed: Macrophage enrichment with the isoflavan glabridin inhibits NADPH oxidase-induced cell-mediated oxidation of low density lipoprotein. A possible role for protein kinase C. PubMed: Human serum paraoxonase (PON 1) is inactivated by oxidized low density lipoprotein and preserved by antioxidants. PubMed: The inhibitory effect of glabridin from licorice extracts on melanogenesis and inflammation. PubMed: Structural aspects of the inhibitory effect of glabridin on LDL oxidation. PubMed: The antioxidative effects of the isoflavan glabridin on endogenous constituents of LDL during its oxidation. PubMed: Licorice extract and its major polyphenol glabridin protect low-density lipoprotein against lipid peroxidation: in vitro and ex vivo studies in humans and in atherosclerotic apolipoprotein E-deficient mice. PubMed: Antioxidant constituents from licorice roots: isolation, structure elucidation and antioxidative capacity toward LDL oxidation. PubMed: [Phenolic constituents of licorice. IV. Correlation of phenolic constituents and licorice specimens from various sources, and inhibitory effects of licorice extracts on xanthine oxidase and monoamine oxidase]. PubMed: Inhibition of adenosine 3',5'-cyclic monophosphate phosphodiesterase by flavonoids from licorice roots and 4-arylcoumarins. PubMed: Identification of antimicrobial and antioxidant constituents from licorice of Russian and Xinjiang origin. PubMed: Antimicrobial agents from higher plants. Antimicrobial isoflavanoids and related substances from Glycyrrhiza glabra L. var. typica.