Carbenoxolone Chemical Properties

Melting point:

291-294 °C

alpha 

D20 +128° (chloroform)

Boiling point:

553.75°C (rough estimate)

Density 

1.20

refractive index 

1.5820 (estimate)

storage temp. 

-20°C Freezer

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

pKa 6.7 (Uncertain)

color 

Cream crystals

Water Solubility 

6.621mg/L(24 ºC)

CAS DataBase Reference

5697-56-3(CAS DataBase Reference)

EPA Substance Registry System

Olean-12-en-29-oic acid, 3-(3-carboxy-1-oxopropoxy)-11-oxo-, (3.beta.,20.beta.)- (5697-56-3)

Safety Information

Toxicity

LD50 orl-rat: 2450 mg/kg OYYAA2 19,323,80

Carbenoxolone Usage And Synthesis

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.

Carbenoxolone(5697-56-3)Related Product Information

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