Литоксолевая кислота

Химические свойства

white to off-white powder

Использование

Lithocholic acid has been used in a study to assess cholestasis and its action on several organs and tissues in rats. It has also been used in a study to investigate the regulation of hepatic phospholipid and bile acid homeostasis through SMAD3 activation by TGFβ.

Определение

ChEBI: A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.

Общее описание

Hexagonal leaflets (from alcohols) or prisms (from acetic acid) or white powder.

Реакции воздуха и воды

Insoluble in water.

Угроза здоровью

ACUTE/CHRONIC HAZARDS: When heated to decomposition LITHOCHOLIC ACID emits acrid smoke and fumes.

Пожароопасность

Flash point data for LITHOCHOLIC ACID are not available. LITHOCHOLIC ACID is probably combustible.

Методы очистки

Lithocholic acid can be purified by conversion to the rather insoluble Na or K salt by addition of the equivalent amount of aqueous NaOH or KOH, filtering off the alkali salt, washing it with ice cold H2O, dissolving it in the least volume of boiling H2O, acidifying with the dilute HCl (slight excess), filtering off the acid, washing with cold H2O and drying it thoroughly in a vacuum. Recrystallise it from Me2CO, EtOH or acetic acid. The methyl ester crystallises from MeOH, with 0.5 mol of MeOH, and has m 92-93o, [] D 25 +34o (MeOH). It has also been purified by recrystallisation from pet ether (b 40-60o) and, after chromatography on Al2O3 in pet ether, gave a labile form m 92-93o which is transformed to the stable form m 125-126o after standing for 2days in a vacuum desiccator. [Hoelm & Mason J Am Chem Soc 62 569 1940, Sarel & Yanuka J Org Chem 24 2018 1959, Beilstein 10 IV 785.]