EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

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

Sponsors

Name:4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol
CAS Number: 59870-68-7Picture of molecule3D/inchi
FDA UNII:HOC5567T41
Nikkaji Web:J649.087E
Beilstein Number:7141956
MDL:MFCD03427694
XlogP3-AA:3.90 (est)
Molecular Weight:324.37620000
Formula:C20 H20 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: bleaching agents
 
Suppliers:
BOC Sciences
For experimental / research use only.
Glabridin >98%
Odor: characteristic
Use: Glabridin is a bio-available isoflavan isolated from licorice (Glycyrrhiza glabra L.) root extract. It has been reported to posses varies biological activities including strong antioxidant activity,
ExtraSynthese
For experimental / research use only.
Glabridin (HPLC) ≥95 %
Jiangyin Healthway
Glabridin - 40 & 90
New functional food ingredients
Jiangyin Healthway
Glabridin
M.C.Biotec
Glabridin - 40 & 90
Odor: characteristic
Use: Tyrosinase Inhibitor: The inhibitory effect on the activity of tyrosinase is stronger than that of Arbutin, Kojic acid, vitamin C and hydroquinone. It can further inhibit the activity of tyrosinase retative protein ( TRP-2)-dopachrome tautomerase. It possesses a quick and highly effective whitening function.
Matrix Scientific
For experimental / research use only.
Glabridin, 95+%
Santa Cruz Biotechnology
For experimental / research use only.
Glabridin
Sigma-Aldrich: Sigma
For experimental / research use only.
Glabridin ≥98% (HPLC), powder
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: natural substances and extractives
Recommendation for glabridin usage levels up to:
 not for fragrance use.
 
Recommendation for glabridin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :124052
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol
Chemidplus:0059870687
 
References:
 4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):124052
Pubchem (sid):135079703
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10421
HMDB (The Human Metabolome Database):HMDB34188
FooDB:FDB012481
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 licorice
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
a polyphenol from licorice extract. Isol. from Glycyrrhiza glabra (licorice)
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