HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Glycyrrhizinsure
GLYCYRRHIZIN · Deglycyrrhizinated Licorice · GLYCYRRHIZINATE · liquorice · 18β-Glycyrrhizic acid · Glycyrrhizic · Glycyrrhizic acid 1405-86-3 · Glycyrrhizine
Identifikatoren & physikalische Daten
| CAS No. | 1405-86-3 |
|---|---|
| Summenformel | C42H62O16 |
| Durchschnittliche Molmasse | 822,9 g/mol |
| Monoisotopische Masse | 822,40378589 g/mol |
| SMILES | CC1(C)[C@@H](O[C@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]12 |
| InChIKey | LPLVUJXQOOQHMX-QWBHMCJMSA-N |
| PubChem CID | 14982 |
| ChEMBL | CHEMBL1927953 |
| ChEBI | CHEBI:15939 |
| EC No. | 215-785-7 |
| DTXSID | DTXSID8047006 |
| Lokaler Name | Glycyrrhizinsure |
Chemische & physikalische Eigenschaften
| XLogP | 3,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 267 |
| H-Brücken-Donoren | 8 |
| H-Brücken-Akzeptoren | 16 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 58 |
| Formalladung | 0 |
| Komplexität | 1.730 |
| LogP (Verteilungskoeffizient) | 2.8log Kow = 2.80 |
| Geschmack | Intensely sweet tasteThe sweetness potency of glycyrrhizin is about 33X (10% sucrose solution sweetness equivalence). |
| Color/Form | Crystals from glacial acetic acidPLATES OR PRISMS FROM ACETIC ACID |
| Löslichkeit | Easily soluble in hot waterFreely sol in hot water, alcoholpractically insol in etherSLIGHTLY SOL IN ETHERDMSO (Slightly), Ethanol (Slightly), Methanol (Sparingly), Pyridine (Slightly) |
| Siedepunkt | Decomposes at 200 ºC681.01°C (rough estimate) |
| Schmelzpunkt | 220220 °C decomposes220°C (rough estimate) |
| Optical Rotation | Specific optical rotation: +46.2 deg @ 17 °C/D (alcohol, 1.5%) |
| Physical Description | Solid with intensely sweet taste[Merck Index] Crystalline plates or prisms[MSDSonline] |
| Collision Cross Section | 288.9 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID8047006]286.8 Ų [M+H]+ [CCS Type: DTSource Identifier: DTXSID5047243]294.4 Ų [M+Na]+ [CCS Type: DT282.6 Ų [M-H]- [CCS Type: DTIonization: ESI-296.2 Ų [M+Na]+ [CCS Type: DT281.7 Ų [M-H]- [CCS Type: DT |
| Other Experimental Properties | ON HYDROLYSIS IT YIELDS GLYCYRRHETIC ACID & 2 MOLES OF GLUCURONIC ACIDSTRUCTURALLY & CHEMICALLY SIMILAR TO ALDOSTERONE & DESOXYCORTICOSTERONESTRUCTURALLY SIMILAR TO MANY CYCLOPENTANOPHENANTHRENE STEROIDSNeedles from 75% aqueous ethanol, decomp 212-217 °C. Specific optical rotation: +46.9 deg @ 20 °C/D (c= 1.5 in 40% ethanol). UV max: 248 nm (e= 11400). Sol in ammonia water, glacial acetic acid. /Ammonium glycycrrhizinate pentahydrate/ |
| Dichte | 1.1442 (rough estimate) |
| Brechungsindex | 61 ° (C=1.5, EtOH) |
| Lagerbedingungen | under inert gas (nitrogen or Argon) at 2-8°C |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 2.76±0.70(Predicted) |
| Farbe | White to Light Yellow |
| Geruch | at 100.00 %. mild spicy |
| Geruchsart | spicy |
| Merck | 14,4505 |
| Stabilität | Hygroscopic |
| Hauptanwendungen | pharmaceutical (small molecule) |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONINGHUMECTANT |
| InChIKey | BXFBITNYMHAJGT-KYXJNIQISA-N |
| LogP (Verteilungskoeffizient) | 4.64 |
| CAS Datenbank | 1405-86-3 |
| EPA chemische Informationen | Glycyrrhizin (1405-86-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 100% (93 of 93) of all reports.Not ClassifiedReported as not meeting GHS hazard criteria by 93 of 93 companies. For more detailed information, please visit ECHA C&L website.Aggregated GHS information provided per 93 reports by companies from 1 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 93 of 93 reports by companies.There are 0 notifications provided by 0 of 93 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: .alpha.-D-Glucopyranosiduronic acid, (3.beta.,20.beta.)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-.beta.-D-glucopyranuronosyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012).alpha.-D-Glucopyranosiduronic acid, (3.beta.,20.beta.)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-.beta.-D-glucopyranuronosyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Emergency treatment: LiquoriceHypokalemia, hypernatremia, and water retention are primary problems associated with chronic liquorice ingestion. Glycyrrhizin is the major active compound (triterpene glycoside) in licorice root. It has been used as an herbal remedy for ulcers, inflammation, and viral infections. After ingestion and hydrolysis, the compound inhibits an enzyme that results in increased serum cortisol levels. [Haddad, p. 485] No adverse effects in the majority of adults expected at doses <100 mg/dayA high intake of liquorice confectionery or herbal tea may exceed 100 mg/day[JECFA] |
| FDA-Anforderungen | Essential oils, oleoresins (solvent-free), and natural extractives (including distillates) that are generally recognized as safe for their intended use within the meaning of section 409 of the act. Licorice is included on this list. /Licorice/Substance added directly to human food affirmed as generally recognized as safe (GRAS). /Licorice and licorice derivatives/ |
| Hazard Classes and Categories | Not Classified |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Wechselwirkungen | ADDITION OF 10-6 M GLYCYRRHETINIC ACID IN PRESENCE OF 10-8 M ALDOSTERONE STIMULATED SHORT-CIRCUIT SIGNIFICANTLY AS COMPARED WITH CONTROL SKIN TREATED WITH ALDOSTERONE ALONE.ADMIN OF GLYCYRRHIZIN DEPRESSED EFFECT OF INJECTED CORTISONE ON GLYCOGEN STORAGE AND ENHANCED IMMUNOSUPPRESSIVE ACTION OF CORTISONE.The pharmacokinetics of total and free prednisolone (PSL) in six healthy men, with or without pretreatment with oral glycyrrhizin (GL), was investigated to confirm whether oral administration of GL influences the metabolism of prednisolone in man. Each subject received an intravenous administration of 0.096 mg/kg of prednisolone hemisuccinate (PSL-HS) with or without pretreatment with 50 mg of oral glycyrrhizin four times. Blood samples were taken from a peripheral vein at 5, 10, 15, 30, 45 min and 1, 1.5, 2, 3, 4, 6, 8, 10, 12 and 24 hr after the start of prednisolone-HS infusion. The concentrations of total prednisolone in plasma were analyzed by high-performance liquid chromatography, and the free prednisolone was measured by an isocolloidosmolar equilibrium dialysis method. The pharmacokinetic parameters of prednisolone were determined by non-compartment analysis. Oral administration of glycyrrhizin was found to significantly increase the concentrations of total prednisolone at 6, 8 hr, and of free prednisolone at 4, 6 and 8 hr after prednisolone-hemisuccinate infusion. Moreover, oral administration of glycyrrhizin was also found to modify the pharmacokinetics of both total and free prednisolone. After oral administration of glycyrrhizin, the area under the curve (AUC) was significantly increased, the total plasma clearance (CL) was significantly decreased, and the mean residence time (MRT) was significantly prolonged. However, the volume of distribution (Vdss) showed no evident change. This suggests that oral administration of glycyrrhizin increases the plasma prednisolone concentrations and influences its pharmacokinetics by inhibiting its metabolism, but not by affecting its distribution.To clarify whether glycyrrhizin, the aqueous extract of licorice root and a drug for treatment of chronic active hepatitis, prevents the development of hepatic injury induced by carbon tetrachloride, allyl formate, and endotoxin, the present study was undertaken in rats. The treatment with glycyrrhizin 20 hr before carbon tetrachloride administration protected the development of the pericentral hepatocellular necrosis. Glycyrrhizin treatment 2 hr prior to the administration of allyl formate also inhibited the development of the periportal hepatocellular necrosis. However, glycyrrhizin did not protect the development of endotoxin-induced focal and random hepatocellular necrosis. These experimental results suggest that glycyrrhizin has no protective effect on hepatic injury following sinusoidal circulatory disturbance as seen in the case of endotoxin and that glycyrrhizin can protect against hepatotoxicity induced by the direct action on the hepatocytes due to hepatotoxins, such as carbon tetrachloride and allyl formate.To investigate the effects of Potenlini on nuclear factor-kappa B (NF-kappa B) binding activity in the livers of animals models with liver cirrhosis, and to delineate the molecular mechanism of the bioactivities of Potenlini. METHODS: Male SD rats were randomly allocated into a normal control group, a model control group, and a Potenlini group. Rats in the latter two groups were treated with CCl4 and Ethanol solution in order to induce chronic liver injury. Rats in Potenlini group were given Potenlini treatment at the same time. All rats were killed at the 9th week after CCl4 administration. Serum and liver specimens were collected, serum ALT activities and histological findings were assessed. Nuclear extracts from liver tissues were prepared and gel retardation assays were performed for the evaluation of NF-kappa B activity. RESULTS: (1) Serum ALT levels were significantly reduced in rats treated with Potenlini compared with those in rats of the model control group, which had dramatically increased ALT levels. (2) Histologically, liver steatosis and fibrosis were severe in the rats of the model group, but were significantly improved in rats of the Potenlini group. (3) NF-kappa B binding activity was markedly increased in the liver specimens taken from the rats of the model control group in comparison with the binding of normal livers, but the binding levels were nearly normal in the livers of the Potenlini group. CONCLUSION: Potenlini can inhibit the NF-kappa B binding activity in CCl4 and ethanol induced chronic liver injury, and that may partially be the mechanism by which Potenlini protects liver from hepatotoxin-induced liver injury and cirrhosis. |
| Toxizitätsübersicht | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org |
| Human Toxicity Excerpts | 14 VOLUNTEERS ATE DAILY DOSES OF 100-200 G LIQUORICE, EQUIV TO O.7-1.4 G GLYCYRRHIZINIC ACID FOR 1-4 WK. PLASMA K CONCN FELLPLASMA RENIN & URINARY ALDOSTERONE DEPPRESSED IN ALL SUBJECTS....TOXICITY OF THIS COMPOUND & ITS DERIVATIVES BY MOUTH IS PRESUMED TO BE LOW. /GLYCYRRHIZA AND ITS DERIVATIVES/POTENTIAL SERIOUS METABOLIC EFFECTS MAY OCCUR IN SOME PEOPLE WHO EAT MODEST AMT OF LIQUORICE DAILY FOR LESS THAN A WEEK.GLYCYRRHIZIC ACID COMPLETELY INHIBITED GROWTH & CYTOPATHIC EFFECTS OF VACCINIA, HERPES SIMPLEX TYPE 1, NEWCASTLE DISEASE & VESICULAR STOMATITIS VIRUSES IN CULTURES OF HUMAN ANEUPLOID HEP2 CELLS.For more Human Toxicity Excerpts (Complete) data for GLYCYRRHIZIN (10 total), please visit the HSDB record page. |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)GlycyrrhizinDILI PositiveDOI:10.1016/j.drudis.2019.09.022 |
| Non-Human Toxicity Excerpts | IN 10-WK DIETARY EXPOSURE, BODY WT GAIN OF RATS SHOWED DOSE-RESPONSE EFFECT. SIGNIFICANT INCR IN DEAD IMPLANTS DURING 1ST WK OF BREEDING AFTER 40,000 PPM IN DIET OF RATS.GLYCYRRHIZIN PROMOTED SODIUM RETENTION BY INHIBITING CORTICOIDS IN LIVER AND INHIBITED METABOLISM OF PROGESTERONE AND ALDOSTERONE.GLYCYRRHETINIC ACID & ITS DERIVATIVES INHIBITED 5BETA-REDUCTION OF CORTISOL, ALDOSTERONE, & TESTOSTERONE BY RAT LIVER PREPN IN VITRO TO GREATER EXTENT THAN 5ALPHA-REDUCTION.A single parenteral and oral administration of ammonium glycyrrhizinate in rat and mice experiments showed that the compound is related to practically nontoxic drugs. Its repeated administration (30 times) into the stomach in a maximum daily therapeutic dose (7 mg/kg) and in a four-fold dose (28 mg/kg) did not cause signs of intoxication, essential changes in the hematological and integral parameters, shifts in the activity of serum enzymes, morphological changes in the cell structures of the internal organs. Administration of the drug in a dose of 28 mg/kg for a second time led to changes in the activity of some enzymes in the brain, the development of parenchymatous dystrophy of the liver which changed to acidophilic necrosis attended with signs of regeneration. Under conditions of a subacute experiment the maximum daily therapeutic dose of ammonium glycyrrhizinate may be considered practically nontoxic.For more Non-Human Toxicity Excerpts (Complete) data for GLYCYRRHIZIN (6 total), please visit the HSDB record page. |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29389090 |
| RTECS-Nr. | MD2025000 |
| Toxizität | human,TDLo,oral,5571ug/kg/3D- (5.571mg/kg),KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION,Toxicologist. Vol. 54, Pg. 109, 2000. |
| Sicherheitshinweise (S) | 22-24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 1405-86-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Glycyrrhizic acid is a triterpene saponin used in the traditional Chinese medicinal preparation for its anti-inflammatory , antiulcerous and antiallergic effects.