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18-alpha-glycyrrhetinic acid
(3beta,18alpha,20beta)-3-hydroxy-11-oxoolean-12-en-29-oic acid

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Name:(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
CAS Number: 1449-05-4Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:215-907-9
FDA UNII: Search
Nikkaji Web:J298.634E
Beilstein Number:2956366
MDL:MFCD00064897
XlogP3-AA:6.40 (est)
Molecular Weight:470.69342000
Formula:C30 H46 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
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: 588.30 °C. @ 760.00 mm Hg (est)
Flash Point: 615.00 °F. TCC ( 323.70 °C. ) (est)
logP (o/w): 6.570 (est)
Soluble in:
 water, 0.01138 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
18-a-Glycyrrhetinic acid >98%
Carbosynth
For experimental / research use only.
18-alpha-Glycyrrhetinic acid
ExtraSynthese
For experimental / research use only.
18-alpha-Glycyrrhetinic Acid (HPLC) ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
18a-Glycyrrhetinic Acid ≥95%
Sigma-Aldrich: Aldrich
For experimental / research use only.
18a-Glycyrrhetinic Acid ≥95%
sds
 
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:
intraperitoneal-mouse LD50 455 mg/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) GASTROINTESTINAL: OTHER CHANGES
Chemical and Pharmaceutical Bulletin. Vol. 28, Pg. 3449, 1980.

intravenous-mouse LD50 100 mg/kg
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02068

oral-mouse LD50 560 mg/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) GASTROINTESTINAL: OTHER CHANGES
Chemical and Pharmaceutical Bulletin. Vol. 28, Pg. 3449, 1980.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for 18-alpha-glycyrrhetinic acid usage levels up to:
 not for fragrance use.
 
Recommendation for 18-alpha-glycyrrhetinic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :73398
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
Chemidplus:0001449054
RTECS:RK0190000 for cas# 1449-05-4
 
References:
 (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):73398
Pubchem (sid):135032829
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB34517
FooDB:FDB013018
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 licorice root
Search Trop Picture
 
Synonyms:
18alpha-glycyrrhetinic acid
3-beta-hydroxy-11-oxo-18-alpha-olean-12-en-30-oic acid
(3beta,18alpha,20beta)-3-hydroxy-11-oxoolean-12-en-29-oic acid
(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
18-alpha-olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo-
 

Articles:

PubMed:Role of gap junction intercellular communication in testicular leydig cell apoptosis induced by oxaliplatin via the mitochondrial pathway.
PubMed:Mutual enhancement of differentiation of osteoblasts and osteocytes occurs through direct cell-cell contact.
PubMed:Age-related impairment of conducted dilation in human coronary arterioles.
PubMed:High-throughput measurement of gap junctional intercellular communication.
PubMed:Basal CD38/cyclic ADP-ribose-dependent signaling mediates ATP release and survival of microglia by modulating connexin 43 hemichannels.
PubMed:Nonsteroidal anti-inflammatory drug activated gene-1 (NAG-1) modulators from natural products as anti-cancer agents.
PubMed:Role of gap junctions modulating hepatic vascular tone in cirrhosis.
PubMed:Inhibitors of ATP release inhibit vesicular nucleotide transporter.
PubMed:Gap junction communication and the propagation of bystander effects induced by microbeam irradiation in human fibroblast cultures: the impact of radiation quality.
PubMed:Dual-energy precursor and nuclear erythroid-related factor 2 activator treatment additively improve redox glutathione levels and neuron survival in aging and Alzheimer mouse neurons upstream of reactive oxygen species.
PubMed:Gap junction expression and the effects of gap junction inhibitors in overactive bladder models: does ovariectomy have a role?
PubMed:Osteoclastogenesis is influenced by modulation of gap junctional communication with antiarrhythmic peptides.
PubMed:Epithelial cell rests of Malassez modulate cell proliferation, differentiation and apoptosis via gap junctional communication under mechanical stretching in vitro.
PubMed:Inhibition of osteoblastic differentiation by warfarin and 18-α-glycyrrhetinic acid.
PubMed:The role of gap junction communication and oxidative stress in the propagation of toxic effects among high-dose α-particle-irradiated human cells.
PubMed:Enhanced connexin 43 expression delays intra-mitotic duration and cell cycle traverse independently of gap junction channel function.
PubMed:Gap junctions and memory: an investigation using a single trial discrimination avoidance task for the neonate chick.
PubMed:Does endothelium-derived hyperpolarizing factor play a role in endothelium-dependent component of electrical field stimulation-induced vasorelaxation of rat mesenteric arterial rings?
PubMed:Possible participation of chloride ion channels in ATP release from cancer cells in suspension.
PubMed:Role of connexin-43 hemichannels in the pathogenesis of Yersinia enterocolitica.
PubMed:ATP release from vascular endothelia occurs across Cx43 hemichannels and is attenuated during hypoxia.
PubMed:Functional role of gap junctions in cytokine-induced leukocyte adhesion to endothelium in vivo.
PubMed:Infusion of gliotoxins or a gap junction blocker in the prelimbic cortex increases alcohol preference in Wistar rats.
PubMed:Selective solid-phase extraction of a triterpene acid from a plant extract by molecularly imprinted polymer.
PubMed:KSHV-transformed primary effusion lymphoma cells induce a VEGF-dependent angiogenesis and establish functional gap junctions with endothelial cells.
PubMed:Endothelium-derived hyperpolarizing factor in preeclampsia: heterogeneous contribution, mechanisms, and morphological prerequisites.
PubMed:Screening of gap junction antagonists on dye coupling in the rabbit retina.
PubMed:Gap-junctional communication is required for mitotic clonal expansion during adipogenesis.
PubMed:Oxidative metabolism of pyruvate is required for meiotic maturation of murine oocytes in vivo.
PubMed:The function of connexin 43 on the differentiation of rat bone marrow cells in culture.
PubMed:ATP release from activated neutrophils occurs via connexin 43 and modulates adenosine-dependent endothelial cell function.
PubMed:Gap junctions and connexon hemichannels in human embryonic stem cells.
PubMed:Carbenoxolone inhibits junctional transfer and upregulates Connexin43 expression by a protein kinase A-dependent pathway.
PubMed:Functional contribution of specific brain areas to absence seizures: role of thalamic gap-junctional coupling.
PubMed:K+ potentiates hyperosmolarity-induced vasorelaxations in rat skeletal muscle arterioles.
PubMed:Staphylococcus aureus-derived peptidoglycan induces Cx43 expression and functional gap junction intercellular communication in microglia.
PubMed:Influence of p53 status on the HSV-Tk/GCV-induced bystander effect in a panel of human ovarian carcinoma cell lines.
PubMed:Consequences of chemoresistance for the herpes simplex virus thymidine kinase/ganciclovir-induced bystander effect in a human small cell lung cancer cell line model.
PubMed:The mechanism of EDHF-mediated responses in subcutaneous small arteries from healthy pregnant women.
PubMed:Selectivity of action of glycyrrhizin derivatives on the growth of MCF-7 and HEP-2 cells.
PubMed:[A simple method for preparation of 18alpha-glycyrretinic acid ant its derivatives].
PubMed:ECM-induced gap junctional communication enhances mammary epithelial cell differentiation.
PubMed:TNF-alpha plus IFN-gamma induce connexin43 expression and formation of gap junctions between human monocytes/macrophages that enhance physiological responses.
PubMed:Uptake of locally applied deoxyglucose, glucose and lactate by axons and Schwann cells of rat vagus nerve.
PubMed:[Bystander effect mediated by herpes simplex virus-thymidine kinase/ganciclovir approach on prostatic cancer cells and its regulation].
PubMed:Ovariectomy attenuates hyperpolarization and relaxation mediated by endothelium-derived hyperpolarizing factor in female rat mesenteric artery: a concomitant decrease in connexin-43 expression.
PubMed:Vascular adaptations to pregnancy in mice: effects on myogenic tone.
PubMed:Bone morphogenetic protein-2 modulation of chondrogenic differentiation in vitro involves gap junction-mediated intercellular communication.
PubMed:The role of gap junctions in mediating endothelium-dependent responses to bradykinin in myometrial small arteries isolated from pregnant women.
PubMed:Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries.
PubMed:Connexin 43-mediated bystander effect in two rat glioma cell models.
PubMed:Retrovirus-mediated transfer of the herpes simplex virus thymidine kinase and connexin26 genes in pancreatic cells results in variable efficiency on the bystander killing: implications for gene therapy.
PubMed:Gap-junctional communication is required for the maturation process of osteoblastic cells in culture.
PubMed:Gap junctions and inhibitory synapses modulate inspiratory motoneuron synchronization.
PubMed:Inhibition of gap-junctional communication induces the trans-differentiation of osteoblasts to an adipocytic phenotype in vitro.
PubMed:Microglia at brain stab wounds express connexin 43 and in vitro form functional gap junctions after treatment with interferon-gamma and tumor necrosis factor-alpha.
PubMed:Immunoglobulin and cytokine expression in mixed lymphocyte cultures is reduced by disruption of gap junction intercellular communication.
PubMed:Gap-junctional communication mediates parathyroid hormone stimulation of mineralization in osteoblastic cultures.
PubMed:Blockade of chloride channels reveals relaxations of rat small mesenteric arteries to raised potassium.
PubMed:Role of gap junctions in endothelium-derived hyperpolarizing factor responses and mechanisms of K(+)-relaxation.
PubMed:Intercellular Ca2+ waves in mechanically stimulated articular chondrocytes.
PubMed:Potassium does not mimic EDHF in rat mesenteric arteries.
PubMed:Role of gap junctions in acetylcholine-induced vasodilation of proximal and distal arteries of the rat mesentery.
PubMed:Synchronization of Ca(2+)-signals within insulin-secreting pseudoislets: effects of gap-junctional uncouplers.
PubMed:A cell type-specific and gap junction-independent mechanism for the herpes simplex virus-1 thymidine kinase gene/ganciclovir-mediated bystander effect.
PubMed:Characterization of nitric oxide- and prostaglandin-independent relaxation in response to acetylcholine in rabbit renal artery.
PubMed:Gap junction intercellular communication mediates the competitive cell proliferation disadvantage of irradiated mouse preimplantation embryos in aggregation chimeras.
PubMed:Mechanisms of coordination of Ca2+ signals in pancreatic islet cells.
PubMed:Determination of urinary 18 beta-glycyrrhetinic acid by gas chromatography and its clinical application in man.
PubMed:The involvement of K+ channels and the possible pathway of EDHF in the rabbit femoral artery.
PubMed:The effects of gap junction blockage on neuronal differentiation of human NTera2/clone D1 cells.
PubMed:Inhibition of the gap junctional component of endothelium-dependent relaxations in rabbit iliac artery by 18-alpha glycyrrhetinic acid.
PubMed:Gap junctional communication and pharmacological heterogeneity in astrocytes cultured from the rat striatum.
PubMed:Functional gap junctions in corneal fibroblasts and myofibroblasts.
PubMed:Astrocytic gap junctional communication decreases neuronal vulnerability to oxidative stress-induced disruption of Ca2+ homeostasis and cell death.
PubMed:Evidence for enhancement of gap junctional coupling between rat island of Calleja granule cells in vitro by the activation of dopamine D3 receptors.
PubMed:Coordinated intercellular calcium waves induced by noradrenaline in rat hepatocytes: dual control by gap junction permeability and agonist.
PubMed:A tumor suppressor gene, Cx26, also mediates the bystander effect in HeLa cells.
PubMed:Gap junctions mediate intercellular calcium signalling in cultured articular chondrocytes.
PubMed:Influence of glycyrrhizin on the evolution and respiration of Ehrlich ascites tumour cells.
PubMed:Gap junction-mediated cell-to-cell communication in bovine and human adrenal cells. A process whereby cells increase their responsiveness to physiological corticotropin concentrations.
PubMed:The effects of 10 triterpenoid compounds on experimental liver injury in mice.
PubMed:Gap junctions in rabbit corneal epithelium: limited permeability and inhibition by cAMP.
PubMed:Growth inhibition of oncogene-transformed rat fibroblasts by cocultured normal cells: relevance of metabolic cooperation mediated by gap junctions.
PubMed:High-performance liquid chromatographic determination of 18 alpha-glycyrrhetinic acid and 18 beta-glycyrrhetinic acid in rat plasma: application to pharmacokinetic study.
PubMed:Developmental change in follicular cell-enhanced amino acid uptake into mouse oocytes that depends on intact gap junctions and transport system Gly.
PubMed:Reversible inhibition of intercellular junctional communication by glycyrrhetinic acid.
 
Notes:
a gap junction inhibitor. Constit. of licorice (Glycyrrhiza glabra) root
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