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

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

Supplier Sponsors

Name:(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-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: 471-53-4Picture of molecule3D/inchi
Other(deleted CASRN):107420-91-7
ECHA EINECS - REACH Pre-Reg:207-444-6
FDA UNII: P540XA09DR
Nikkaji Web:J5.943I
Beilstein Number:2229654
MDL:MFCD00003706
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:cosmetic ingredient for skin conditioning
 
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
Melting Point: 296.00 °C. @ 760.00 mm Hg
Boiling Point: 588.34 °C. @ 760.00 mm Hg (est)
Flash Point: 615.00 °F. TCC ( 323.70 °C. ) (est)
logP (o/w): 5.498 (est)
Soluble in:
 water, 0.01138 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Glycyrrhetinic acid 98%
BOC Sciences
For experimental / research use only.
18-beta-Glycyrrhetintic Acid >98%
Odor: characteristic
Use: Enoxolone is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice.
Coompo
For experimental / research use only.
18-beta-Glycyrrhetinic acid from Plants ≥98%
Odor: characteristic
Use: Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid. It is used in flavoring and it masks the bitter taste of drugs like aloe and quinine. It is effective in the treatment of peptic ulcer and also has expectorant (antitussive) properties. It has some additional pharmacological properties including antiviral, antifungal, antiprotozoal, and antibacterial activities. Antibacterial, antitussive agent. Used in treatment of noninfective inflammatory disorders (skin, mouth, etc.)
ExtraSynthese
For experimental / research use only.
18-beta-Glycyrrhetinic Acid (HPLC) ≥99%
Glentham Life Sciences
Enoxolone
Jiangyin Healthway
18b-Glycyrrhetinic Acid (Enoxolone)
New functional food ingredients
Jiangyin Healthway
18b-glycyrrhetinic Acid
Nacalai USA
For experimental / research use only.
18b-Glycyrrhetinic Acid
Penta International
18-BETA-GLYCYRRHETINIC ACID
Santa Cruz Biotechnology
For experimental / research use only.
18 β-Glycyrrhetinic Acid
Sigma-Aldrich: Aldrich
For experimental / research use only.
18β-Glycyrrhetinic acid 97%
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 308 mg/kg
Drugs in Japan Vol. -, Pg. 319, 1990.

intravenous-mouse LD50 56 mg/kg
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02067

Dermal Toxicity:
subcutaneous-mouse LD50 518 mg/kg
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 5, Pg. 98, 1963.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
cosmetic ingredient for skin conditioning
Recommendation for 18-beta-glycyrrhetinic acid usage levels up to:
 not for fragrance use.
 
Recommendation for 18-beta-glycyrrhetinic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):471-53-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10114
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-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:0000471534
RTECS:RK0180000 for cas# 471-53-4
 
References:
 (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-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):10114
Pubchem (sid):134975336
 
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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C02283
HMDB (The Human Metabolome Database):HMDB11628
FooDB:FDB020713
Export Tariff Code:2918.90.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 arthrodont
 biosone
 BX-1
 enoloxone
 enoxolone
 enoxolonum
18b-glycyrrhetinic acid
18beta-glycyrrhetinic acid
 hidermart
(3b,20b)-3-hydroxy-11-oxoolean-12-en-29-oic acid
3b-hydroxy-11-oxoolean-12-en-30-oic acid
(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-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
 rhetinic acid
 uralenic acid
 

Articles:

PubMed:18β-glycyrrhetinic acid attenuates anandamide-induced adiposity and high-fat diet induced obesity.
PubMed:Glycyrrhetinic Acid Suppressed NF-κB Activation in TNF-α-Induced Hepatocytes.
PubMed:Anti-inflammatory effects of 27 selected terpenoid compounds tested through modulating Th1/Th2 cytokine secretion profiles using murine primary splenocytes.
PubMed:Water extract of licorice had anti-viral activity against human respiratory syncytial virus in human respiratory tract cell lines.
PubMed:Metabolism of ginger component [6]-shogaol in liver microsomes from mouse, rat, dog, monkey, and human.
PubMed:Glycyrrhizic acid and 18β-glycyrrhetinic acid recover glucocorticoid resistance via PI3K-induced AP1, CRE and NFAT activation.
PubMed:Glycyrrhizic acid and 18β-glycyrrhetinic acid modulate lipopolysaccharide-induced inflammatory response by suppression of NF-κB through PI3K p110δ and p110γ inhibitions.
PubMed:In vitro and in vivo pharmacokinetics of two novel 1,3-cyclic propanyl phosphate ester prodrugs of 18β-glycyrrhetic acid in rats.
PubMed:Glycyrrhizic acid and 18beta-glycyrrhetinic acid inhibit inflammation via PI3K/Akt/GSK3beta signaling and glucocorticoid receptor activation.
PubMed:Inhibition of human renin activity by saponins.
PubMed:Determination of glycyrrhetic acid after consumption of liquorice and application to a fatality.
PubMed:Licorice: a sweet alternative to prevent hyperkalemia in dialysis patients?
PubMed:Glycyrrhetinic acid food supplementation lowers serum potassium concentration in chronic hemodialysis patients.
PubMed:Glycyrrhizin and licorice significantly affect the pharmacokinetics of methotrexate in rats.
PubMed:Neuroprotective effects of glycyrrhizic acid and 18beta-glycyrrhetinic acid in PC12 cells via modulation of the PI3K/Akt pathway.
PubMed:Effect of the extracts from Glycyrrhiza uralensis Fisch on the growth characteristics of human cell lines: Anti-tumor and immune activation activities.
PubMed:[Hypertension due to liquorice and liquorice tea consumption].
PubMed:Effects of 11beta-hydroxysteroid dehydrogenase inhibitor on body weight and glucose tolerance in Sprague-Dawley rats fed with a high-fat diet.
PubMed:Blockade of cytokine-induced endothelial cell adhesion molecule expression by licorice isoliquiritigenin through NF-kappaB signal disruption.
PubMed:Simultaneous quantification of flavonoids and triterpenoids in licorice using HPLC.
PubMed:Simultaneous HPLC analysis, with isocratic elution, of glycyrrhizin and glycyrrhetic acid in liquorice roots and confectionery products.
PubMed:The old lady who liked liquorice: hypertension due to chronic intoxication in a memory-impaired patient.
PubMed:Severe hypokalaemic paralysis and rhabdomyolysis due to ingestion of liquorice.
PubMed:Different responsiveness in body weight and hepatic 11beta-hydroxysteroid dehydrogenase (11beta-HSD) type 1 mrna to 11beta-HSD inhibition by glycyrrhetinic acid treatment in obese and lean zucker rats.
PubMed:Effects of Sho-saiko-to extract and its components, Baicalin, baicalein, glycyrrhizin and glycyrrhetic acid, on pharmacokinetic behavior of salicylamide in carbon tetrachloride intoxicated rats.
PubMed:Anti-allergic activity of 18beta-glycyrrhetinic acid-3-O-beta-D-glucuronide.
PubMed:Biological activity of some naturally occurring resins, gums and pigments against in vitro LDL oxidation.
PubMed:[Immunological study on the antitumor effects of fungus polysaccharides compounds].
PubMed:Efficient method for determining the glycyrrhizin content of fresh and dried roots, and root extracts, of Glycyrrhiza species.
PubMed:The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling.
PubMed:Isolation and identification of main constituents in an enzymatically hydrolysed licorice extract sweetener.
PubMed:A population physiologically based pharmacokinetic/pharmacodynamic model for the inhibition of 11-beta-hydroxysteroid dehydrogenase activity by glycyrrhetic acid.
PubMed:Physiologically based pharmacokinetic modeling of glycyrrhizic acid, a compound subject to presystemic metabolism and enterohepatic cycling.
PubMed:Localization of enzymes involved in metabolism of glycyrrhizin in contents of rat gastrointestinal tract.
PubMed:Glycyrrhizic acid in liquorice--evaluation of health hazard.
PubMed:Inhibition of mutagenicity in Salmonella typhimurium and skin tumor initiating and tumor promoting activities in SENCAR mice by glycyrrhetinic acid: comparison of 18 alpha- and 18 beta-stereoisomers.
PubMed:The determination of glycyrrhizin in selected UK liquorice products.
PubMed:Teratogenicity study of ammonium glycyrrhizinate in the Sprague-Dawley rat.
PubMed:[Estimation of daily intake of glycyrrhizic acid according to the market basket studies in Japan (I)].
PubMed:[Glycyrrhizin levels in various food stuffs].
PubMed:Tests for mutagenic effects of ammoniated glycyrrhizin, butylated hydroxytoluene, and gum Arabic in rodent germ cells.
PubMed:Tumorigenicity study of disodium glycyrrhizinate administered orally to mice.
PubMed:Effects of carbenoxolone on gastric release of prostaglandin (PG)E2 in patients with peptic ulcer disease.
PubMed:Effect of carbenoxolone on gastric prostaglandin E2 levels in patients with peptic ulcer disease following vagal and pentagastrin stimulation.
PubMed:[STudies on the likelihood of growth of Streptococcus faecium following thermal treatment in meat suspensions (author's transl)].
 
Notes:
an oleanolic acid from glycyrrhiza that has some antiallergic, antibacterial, and antiviral properties. it is used topically for allergic or infectious skin inflammation and orally for its aldosterone effects in electrolyte regulation. Aglycone from licorice (Glycyrrhiza glabra) Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice. It is used in flavoring and it masks the bitter taste of drugs like aloe and quinine. (Wikipedia)
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