LITHOCHOLIC ACID

LITHOCHOLIC ACID Basic information
Product Name:LITHOCHOLIC ACID
Synonyms:17-beta-(1-Methyl-3-carboxypropyl)ethiocholan-3-alpha-ol;17beta-(1-methyl-3-carboxypropyl)etiocholan-3alpha-ol;BETA-CHOLANIC ACID-3-ALPHA-OL;HYDROYCHOLANIC ACID;3-HYDROXYCHOLANIC ACID;3ALPHA-HYDROXYCHOLANIC ACID;3ALPHA-HYDROXY-5BETA-CHOLANIC ACID;3ALPHA-HYDROXY-5BETA-CHOLAN-24-OIC ACID
CAS:434-13-9
MF:C24H40O3
MW:376.57
EINECS:207-099-1
Product Categories:Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Bile Acids;Biochemistry
Mol File:434-13-9.mol
LITHOCHOLIC ACID Structure
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)
Fp 9℃
storage temp. room temp
solubility Chloroform (Slightly), Dichloromethane (Slightly, Heated), DMSO (Slightly, Heated)
pka4.76±0.10(Predicted)
form Powder
color White to off-white
Water Solubility 18.83ug/L(25 ºC)
Merck 5545
BRN 3217757
InChIKeySMEROWZSTRWXGI-HVATVPOCSA-N
LogP6.700 (est)
CAS DataBase Reference434-13-9(CAS DataBase Reference)
EPA Substance Registry SystemLithocholic 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 Data434-13-9(Hazardous Substances Data)
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
LITHOCHOLIC ACID Usage And Synthesis
Chemical Propertieswhite to off-white powder
UsesCholagogue;Anticholelithogenic
UsesLD50(mouse) 3900 mg/kg po
UsesA cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.
UsesLithocholic 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.
DefinitionChEBI: 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 DescriptionHexagonal leaflets (from alcohols) or prisms (from acetic acid) or white powder.
Air & Water ReactionsInsoluble in water.
Health HazardACUTE/CHRONIC HAZARDS: When heated to decomposition LITHOCHOLIC ACID emits acrid smoke and fumes.
Fire HazardFlash point data for LITHOCHOLIC ACID are not available. LITHOCHOLIC ACID is probably combustible.
Biological Activitylithocholic acid (lca) is a toxic secondary bile acid, causing intrahepatic cholestasis, which has tumor-promoting activity.
in vitroamong 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 vivoadministration 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 MethodsLithocholic 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.
LITHOCHOLIC ACID Preparation Products And Raw materials
Raw materialsChola-4,22-dien-24-oic acid, 3-oxo-, ethyl ester, (22E)--->3α-Acetoxy-5β-cholan-24-oic acid methyl ester
METHYL DESOXYCHOLATE Sodium cholate 5BETA-CHOLANIC ACID-3ALPHA,12ALPHA-DIOL 3-ACETATE METHYL ESTER HYOCHOLIC ACID HYODEOXYCHOLIC ACID SODIUM SALT 12-DEHYDROCHOLIC ACID METHYL ESTER 3α,12α-Diacetoxy-5β-cholan-24-oic acid methyl ester DEOXYCHOLIC ACID SODIUM SALT MONOHYDRATE 12-OXOCHENODEOXYCHOLIC ACID HYODEOXYCHOLIC ACID METHYL ESTER 5B-CHOLANIC ACID-3A-OL-12-ONE3-BENZOATE METHYL EST 5BETA-CHOLANIC ACID-3ALPHA,12ALPHA-DIOL 3-CARBETHOXYLATE METHYL ESTER LABOTEST-BB LT00454505 URSODEOXYCHOLIC ACID SODIUM SALT 3ALPHA,7ALPHA-DIACETOXY-5BETA-CHOLAN-24-OIC ACID METHYL ESTER 5-BETA-CHOLANIC ACID-3-ALPHA, 7-ALPHA, 12-ALPHA-TRIOL 3,7-DIACETATE METHYL ESTER SODIUMLITHOCHOLATE CHENODEOXYCHOLIC ACID SODIUM SALT

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