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Enoxolon

18β-Glycyrrhetinic Acid

HCID 18526330
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Grundinformationen

CAS
471-53-4
Standard-SMILES
CC1(C)C2CC[C@]3(C)C(C(=O)C=C4C5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O
Summenformel
C30H46O4
Durchschnittliche Molmasse
470,68 g/mol

Namen und Bezeichner

Bevorzugter Name
18β-Glycyrrhetinic Acid
Lokaler Name
Enoxolon
Englischer Name
18β-Glycyrrhetinic Acid
Summenformel
C30H46O4
Molmasse
470.68

Namen und Synonyme

GLYCYRRHETINIC ACIDENOXOLONEGLYCYRRHETIC ACID18B-GLYCYRRHETINIC ACIDGlycyrrhetinateGlycyrrhetinicbiosone18β-Glycyrrhetic acidRhetinic acidglycyrrhetin

Datenbank-Bezeichner

CAS
471-53-4
PubChem CID
18526330

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt
292 · 292-295 °C(lit.)
Siedepunkt
492.11 °C · 492.11°C (rough estimate)
Dichte
0.9967 · 0.9967 (rough estimate)
Dampfdruck
10 · 10-220Pa at 20-50℃
Brechungsindex
162 ° · 162 ° (C=1, MeOH)
storage temp.
2 · 2-8°C
Löslichkeit
Practically insoluble in water, soluble in ethanol, sparingly soluble in methylene chloride.
pka
5.56 · pKa 5.56±0.1 (Uncertain)
Aggregatzustand
Crystalline Powder
Farbe
White to off-white
Wasserlöslichkeit
SOLUBLE IN ACETIC ACID
Merck
14 · 14,3590
BRN
2229654 · 2229654
Kosmetik-Inhaltsstoffe Funktionen
SKIN CONDITIONING
InChIKey
MPDGHEJMBKOTSU-YKLVYJNSSA-N
SMILES
CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]3(C)[C@@H]2C(=O)C=C4[C@@H]5C[C@](C)(CC[C@]5(C)CC[C@@]34C)C(O)=O
LogP
4.5 at · 4.5 at 20℃
CAS Datenbank
471 · 471-53-4(CAS DataBase Reference)
EPA chemische Informationen
Enoxolone (471-53-4)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
29189900
RTECS-Nr.
RK0180000
risk_code
22-36
Toxizität
mouse,LD50,intraperitoneal,308mg/kg (308mg/kg),Drugs in Japan Vol. -, Pg. 319, 1990.
hazard_code
Xn
safety_code
22-24/25
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Anwendungen · 3 Einträge

BeschreibungExtracting from liquorice (Glycyrrhiza uralensis Fisch, Gan Cao), glycyrrhetic acid also can be detected in other plants, such as Abrus cantoniensis Hance and Herba Abri fruticulosi. As one of traditional Chinese medicines, liquorice has been applied clinically for a long period. Due to its extensive usage, it plays an extremely important role in traditional Chinese medicine formula mainly as “guide” drug. As is recorded in Shen Nong’s Herbal Classic and later in pharmaceutical monographs, liquorice is able to strengthen bones and muscles and enhance metabolism and detoxification. Also, abnormal symptoms of the body and wound can be improved. Glycyrrhetic acid, the most important and potent ingredient of liquorice, has been recorded in Pharmacopoeia of the People’s Republic of China.

HistoryGlycyrrhetic acid originates from hydrolysis of glycyrrhizin, which has a therapeutic effect on disease. Dating back to the 1930s, the chemical structure of glycyrrhetic acid was demonstrated . Subsequently, the discovery of antiulcer activity promotes following research . The ramification of glycyrrhetic acid, carbenoxolone sodium, has a therapeutic effect on ulcer. In 2010, followed by the approval of raw materials, batches of tablets and capsules were approved in 2009, respectively. In foreign countries, 18β-glycyrrhetic acid was studied for anti-inflammatory effect on arthritis, rheumatoid disease, and periodontitis in BioNetWorks. The company applied for the patent of 18β-glycyrrhetic acid in 1999. Also, after joining the leading worldwide market in 2006, phase III clinical trials would be carried out in 2007. However, the progress was hindered in 2008. To detecting more indications, its carbenoxolone sodium was studied by other three companies: after conducting phase III clinical trials in the UK, the project of RB intending to improve nonspecific inflammatory bowel disease was given up in 1992. York Pharma expected to make progress in psoriasis with gel or cream; however, the project has been in a standstill after phase II clinical trials was conducted from 2005 to 2009. Canada pharmaceutical company, Oxalys Pharmaceuticals, research it for treating Huntington’s disease, and it was included in the orphan drug list by the USA in 2014. Till now, phase I clinical trials are still continuing.

VerwendenThe product may be used as a starting material to prepare 18β-glycyrrhetinic acid derivatives, which show anti-inflammatory and antioxidant properties.

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Vorgelagerte Rohstoffe

GlycyrrhizinsureSISEthanolTriammonium glycyrrhizinateSaccharoseDGLEthanol solution18α-GlycylrrhizinWasserHydrogenchlorid

Nachgelagerte Produkte

Stearyl glycyrrhetinate

Ergänzende Hinweise

DefinitionChEBI: A pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30.