5697-56-3

Basic information

• Product Name: Carbenoxolone
• Synonyms: CARBENOXOLONE;glycyrrhetinic acid hydrogen succinate;3beta-Hydroxy-11-oxoolean-12-en-30-oic acid hydrogen succinate;Olean-12-en-29-oic acid,3-(3-carboxy-1-oxopropoxy)-11-oxo-,(3b,20b)-;3β-[(β-Carboxypropionyl)oxy]-11-oxoolean-12-en-30-oic acid;CARBENOXOLONE(RG);2-Methylidene-2,3-dihydrofuran-3-one;CARBENOXOLONE [U
• CAS NO: 5697-56-3
• Molecular Formula: C₃₄H₅₀O₇
• Molecular Weight: 570.76
• EINECS: 227-174-2
• Product Categories: Pentacyclic Triterpenes
• Mol File: 5697-56-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 291-294 °C
• Boiling Point: 553.75°C (rough estimate)
• Flash Point: 211.6 °C
• Appearance: /
• Density: 1.20
• Vapor Pressure: 1.06E-20mmHg at 25°C
• Refractive Index: 1.5820 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: pKa 6.7 (Uncertain)
• Water Solubility: 6.621mg/L(24 oC)
• CAS DataBase Reference: Carbenoxolone(CAS DataBase Reference)
• NIST Chemistry Reference: Carbenoxolone(5697-56-3)
• EPA Substance Registry System: Carbenoxolone(5697-56-3)

Safety Data

• Hazardous Substances Data: 5697-56-3(Hazardous Substances Data)

Usage

Originator

Biogastrone,Winthrop,UK,1963

Uses

Glucocorticoid.

Manufacturing Process

23.5 g of glycyrrhetinic acid were dissolved in 50 cc of dry pyridine. A solution of 6.0 g of succinic anhydride in 30 cc of dry pyridine was added, followed by 30 cc of dry triethylamine and then, for washing purposes, 5 cc of dry pyridine. The solution was heated on a boiling water bath for ten hours and then poured into excess of dilute hydrochloric acid and ice. The fine gray precipitate formed was filtered off, washed with water, dissolved in chloroform, and the solution repeatedly extracted with dilute hydrochloric acid and later with water. It was dried over sodium sulfate and evaporated to dryness. Crystallization from methanol, using charcoal to effect decolorization, gave the hydrogen succinate as cream-colored crystals, MP 291° to 294°C, with previous softening.One molecular proportion of glycyrrhetinic acid hydrogen succinate was ground with a dilute (5%) aqueous solution containing two molecular proportions of sodium hydroxide. The solution was filtered and evaporated in vacuum over concentrated sulfuric acid. The sodium salt is then obtained as a creamy white water-soluble solid. Glycyrrhetinic acid is obtainable from licorice root.

Therapeutic Function

Antiinflammatory (gastric)

Safety Profile

Poison by intravenous andintraperitoneal routes. Moderately toxic by ingestion andsubcutaneous routes. Human systemic effects byingestion: muscle weakness and flaccid paralysis. Whenheated to decomposition it emits acrid smoke and fumes.

InChI:InChI=1/C34H50O7.2Na/c1-29(2)23-10-13-34(7)27(32(23,5)12-11-24(29)41-26(38)9-8-25(36)37)22(35)18-20-21-19-31(4,28(39)40)15-14-30(21,3)16-17-33(20,34)6;;/h18,21,23-24,27H,8-17,19H2,1-7H3,(H,36,37)(H,39,40);;/q;2*+1/p-2/t21-,23?,24-,27?,30+,31-,32-,33+,34+;;/m0../s1

Upstream product

• 471-53-4 enoxolone 
• 45160-42-7 succinic anhydride 
• 108-30-5 succinic acid anhydride 

Relevant articles and documents

Glycyrrhetinic acid derivative ASBT as well as preparation method and application thereof

The invention discloses a glycyrrhetinic acid derivative ASBT as well as a preparation method and application thereof, and the glycyrrhetinic acid derivative ASBT disclosed by the invention has a structure shown as a general formula I. The preparation method has the beneficial effects that the synthesis is simple, the reaction conditions are mild, and the like.

Glycyrrhetinic acid derivative BGU as well as preparation method and application thereof

The invention discloses a glycyrrhetinic acid derivative BGU as well as a preparation method and application thereof, and the glycyrrhetinic acid derivative BGU has a structure as shown in a general formula I. The preparation method has the beneficial effects that the synthesis is simple, the reaction conditions are mild, and the like.

Glycyrrhetinic acid-modified PEG-PCL copolymeric micelles for the delivery of curcumin

In this study, glycyrrhetinic acid (GA) was conjugated with mono amino poly (ethylene glycol)-b-poly (ε-caprolactone) (H2N-PEG-PCL) with succinate linker to obtain the GA-modified PEG-PCL (GA-PEG-PCL). By way of thin film hydration method, curcumin was encapsulated into GA-PEG-PCL copolymer to form stable micelles with 93.76% of encapsulation efficiency and 11.93% of drug loading capacity. The micelles enhanced curcumin's water-solubility to 1.87 mg/ml, being 1.70 × 105 times higher than free curcumin. X-ray diffraction and FT-IR analysis confirmed the encapsulation of CUR into copolymeic micelles with an amorphous state. Hemolysis datum of blank micelles showed its biocompatibility. Compared with GA-unconjugated micelles, curcumin-loaded GA-PEG-PCL micelles showed slower in vitro release of drug, but they displayed better in vitro cytotoxicity against HepG2 at about 40 μM because of its selective accumulation in HepG2 cells induced by GA. The results showed that GA-PEG-PCL copolymer could be a promising drug carrier for liver targeted drug delivery.