18-beta-glycyrrhetinic acid

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

CAS: 471-53-4 C30 H46 O4 MW: 470.69342000

Identification

Name18-beta-glycyrrhetinic acid
IUPAC(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 Number471-53-4
EINECS207-444-6
FDA UNIIP540XA09DR
Molecular FormulaC30 H46 O4
Molecular Weight470.69342000
MDL NumberMFCD00003706
Nikkaji NumberJ5.943I
Beilstein2229654

Regulatory

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)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesskin conditioning

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 308 mg/kg
Dermal Toxicitysubcutaneous-mouse LD50 518 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02067']

Safety in Use

Categorycosmetic ingredient for skin conditioning
Recommendation for 18-beta-glycyrrhetinic acid usage levels up tonot for fragrance use.
Recommendation for 18-beta-glycyrrhetinic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

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 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)].