リトコール酸 化学特性,用途語,生産方法
外観
白色の結晶又は結晶性の粉末(JP法)
溶解性
エタノールに溶けやすく、水にほとんど溶けない。
解説
リトコール酸，“litho”は石を意味する無色の板状晶．融点184～186 ℃．[α]D20"＋33.7°(エタノール)．熱エタノールに易溶，酢酸エチルに可溶，石油エーテル，リグロイン，水に不溶．経口投与すると胆石形成，肝硬変症を引き起こすほど毒性があるが，硫酸抱合されると尿中に排泄される．
森北出版「化学辞典（第2版）
用途
ステロイドの骨格構造研究。
製法
リトコール酸，ウシ，ヒト，ウサギの胆汁およびウシ，ブタの胆石のなかに存在する．コール酸，デオキシコール酸の類縁化合物で，それらから合成され，多くは糞便中に排泄される．
効能
胆汁酸の一種
化学的特性
white to off-white powder
使用
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.
定義
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.
一般的な説明
Hexagonal leaflets (from alcohols) or prisms (from acetic acid) or white powder.
空気と水の反応
Insoluble in water.
健康ハザード
ACUTE/CHRONIC HAZARDS: When heated to decomposition LITHOCHOLIC ACID emits acrid smoke and fumes.
火災危険
Flash point data for LITHOCHOLIC ACID are not available. LITHOCHOLIC ACID is probably combustible.
純化方法
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.]
参考文献
S. Sarel, Y. Yanuka, J. Org. Chem., 24, 2018 (1959), DOI: 10.1021/jo01094a602.
リトコール酸 上流と下流の製品情報
原材料
準備製品