LITHOCHOLIC ACID Chemical Properties

Melting point:

183-188 °C (lit.)

alpha 

D20 +33.7° (c = 1.5 in abs ethanol); D19 +23.3° (Wieland); D20 +32.1° (Fischer)

Boiling point:

445.09°C (rough estimate)

Density 

1.0454 (rough estimate)

refractive index 

35.5 ° (C=1, EtOH)

Flash point:

9℃

storage temp. 

room temp

solubility 

Chloroform (Slightly), Dichloromethane (Slightly, Heated), DMSO (Slightly, Heated)

pka

4.76±0.10(Predicted)

form 

Powder

color 

White to off-white

optical activity

+3220 (c 1.5, ethanol)

Water Solubility 

18.83ug/L(25 ºC)

Merck 

5545

BRN 

3217757

InChIKey

SMEROWZSTRWXGI-HVATVPOCSA-N

LogP

6.700 (est)

CAS DataBase Reference

434-13-9(CAS DataBase Reference)

EPA Substance Registry System

Lithocholic acid (434-13-9)

Safety Information

Safety Statements 

22-24/25

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

2

RTECS 

FZ2275000

HS Code 

29181998

Hazardous Substances Data

434-13-9(Hazardous Substances Data)

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

LITHOCHOLIC ACID Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

LD50(mouse) 3900 mg/kg po

Uses

Cholagogue;Anticholelithogenic

Uses

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.

Uses

A cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.

Definition

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.

General Description

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

Air & Water Reactions

Insoluble in water.

Health Hazard

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

Fire Hazard

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

Biological Activity

lithocholic acid (lca) is a toxic secondary bile acid, causing intrahepatic cholestasis, which has tumor-promoting activity.

in vitro

among 17 kinds of bile acids with respect to inhibition of mammalian dna polymerases, only lca and its derivatives inhibited dna polymerases, while other bile acids did not show inhibitory effect [1].

in vivo

administration of lca and its conjugates to rodents causes intrahepatic cholestasis, which is a pathogenic state characterized by decreased bile flow and the accumulation of bile constituents in the liver and blood [2].

Purification Methods

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.]

References

[1] ogawa a, murate t, suzuki m, nimura y, yoshida s. lithocholic acid, a putative tumor promoter, inhibits mammalian dna polymerase beta. jpn j cancer res. 1998 nov;89(11):1154-9.
[2] staudinger jl, goodwin b, jones sa, hawkins-brown d, mackenzie ki, latour a, liu y, klaassen cd, brown kk, reinhard j, willson tm, koller bh, kliewer sa. the nuclear receptor pxr is a lithocholic acid sensor that protects against liver toxicity. proc natl acad sci u s a. 2001 mar 13;98(6):3369-74.

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