Cholic acid CAS: 81-25-4 Basic information
|Product Name:||Cholic acid|
|Synonyms:||3,7,12-Trihydroxy-cholan-24-oic acid;5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy-;Cholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7alpha,12alpha)-;3,7,12-TRIHYDROXYCHOLANIC ACID;3A,7A,12A-TRIHYDROXY-5B-CHOLAN-24-OIC ACID;3ALPHA, 7ALPH|
|Product Categories:||Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;|
Cholic acid CAS: 81-25-4 Chemical Properties
|density:||1.0310 (rough estimate)|
|Melting point:||200-201 °C(lit.)|
|Boiling point:||449.08°C (rough estimate)|
|storage temp.:||Store at RT.|
|Water Solubility:||0.28 g/L (15 ºC)|
|refractive index:||1.5800 (estimate)|
|solubility:||methanol: 0.1 g/mL, clear|
|NIST Chemistry Reference:||Cholic acid(81-25-4)|
|alpha:||36 º (c=0.6, 95% EtOH)|
|CAS DataBase Reference:||81-25-4(CAS DataBase Reference)|
|EPA Substance Registry System:||Cholan-24-oic acid, 3,7,12-trihydroxy-, (3.alpha.,5.beta.,7.alpha.,12.alpha.)- (81-25-4)|
White powder,Odorless, slightly bitter
Add acetic acid solution and strain. Add a freshly prepared furfural solution and heat it in a water bath. The solution should be blue-purple
Take 0.5g of this product, add ethanol to heat the ultrasonic treatment for dissolution, static, the solution should be clarified without obvious precipitation
Loss on drying
Residue on ignition
|Cholic acid Usage And Synthesis|
|Chemical properties||This agent exist in the bile cattle, sheep, pig. It is a colorless sheet or white crystalline powder. Some have a bitter to sweet taste. Its melting point is 198℃, specific rotation is (c = 0.6, ethanol) +37°. 1g cholic acid dissolved in about 300ml ethanol or acetone, 7ml glacial acetic acid. A small amount of cholic acid is soluble in water. The monohydrate was a white flake crystal. In 1927, H.Wieland (Germany) research accomplished bile acid composition, and won the Nobel Prize in chemistry.|
(2) Used for biochemical research, as pharmaceutical intermediates. Sodium cholate is a cholagogue, for the treatment of cholecystitis, bile deficiency, intestinal indigestion embolism.
(3) As organic acids with steroid structure, cholic acid can emulsify fat, promote its digestion.
(4) Non-denaturing ionic detergents for the extraction of membrane proteins.
|Identification test||Solubility: hardly insoluble in water; soluble in ethanol. According to OT-42 method.|
The melting range : 197~202 ℃. As determined by conventional methods.
Add 50% acetic acid solution to prepare 0.02% of the sample solution; take 1ml, 1% furfural solution, 6ml of water and concentrated sulfuric acid 5ml. This mixture should be converted into rosiness in 5min and then turn purple.
Take about 10mg sample, add 2 drops of benzaldehyde and 3: 1 sulfuric acid 3 drops, heating at 50 ℃ for 5min. Plus glacial acetic acid about 10ml, then it should be brown.
|Analysis of the content||Weigh about 400mg of the sample accurately; dried at 140 ℃ for 4h; put it into a 250ml flask; add 20ml of water and 40ml of ethanol; cover the surface dish, and gently heat to dissolve and cool in the steam bath. Add 5 drops of phenolphthalein test solution (TS-167), titrate with 0.1mol/L sodium hydroxide solution to pink and keep 15s, and make the necessary correction with the same time blank test. Each 1ml of 0.1 mol/L sodium hydroxide corresponds to 40.86 mg of cholic acid (C24 H40O5).|
ADI O~1.25 mg/kg (FAO/WH0, 2001)。
|Production methods||(1) Extracting from livestock (pigs, cattle, sheep, rabbits) the bile.|
1.Ethanol crystallization method
Preparation of crude cholic acid of cattle, sheep: take bovine or sheep bile; add 100 g/L sodium hydroxide; heat to boil for 12-18h to get saponification solution. Cooling. Adding acid to pH 1, precipitating cholic acid, removing bile acid, undergoing boiling and rinsing, drying at 75℃, milling can obtain bovine cholic acid.
sodium cholate[NaOH] → [100 ℃, 12-18h] saponified solution[H2SO4] → [pH1, 75 ℃] crude cholic acid of cattle, sheep.
Preparation of sodium cholate: add 0.5-1 times of crude cholic acid to 95% ethanol, and dissolve the solids by heating reflux method; cool. Broke the crystallization; filter; add 95% washing ethanol to make the filtrate colorless. Crystallize by adding 4 times the amount of ethanol; add 100-150g/L of activated carbon; dissolve the solids by heating reflux method; filter the liquid when it is hot. The filtrate concentrated to the original volume of 1/4. Through cooling, crystallization, filtration, adding ethanol to wash the crystallization can obtain the sodium cholate products.
Crude cholic acid cattle, sheep [ethanol, activated carbon] → refined liquid [90 ℃ below] → sodium cholate products
2. Ethyl acetate separation method
Preparation of crude hyocholic acid: Add 3-3.5 times of saturated lime supernatant into fresh pig bile under stirring, then continue to stir it for 5-10min. heating to boiling for 2min, cooling, through filtration, adding hydrochloric acid to PH3.5 to get precipitation, standing for more than 12h can obtain crude acid. Removing, washing, adding 1.5 times the sodium hydroxide, plus 9 times the water, heating and boiling 12-18h, cooling, standing overnight obtain paste. Add water and sulfuric acid to pH 1 to precipitate pig cholic acid. Removing, crushing, rinsing to no acidity, through filtration gains crude pig cholic acid.
[pig bile] [saturated limewater] →[100℃, pH 11-12] Basic filtrate [HCl] → [pH3.5] Crude cholic acid [water, NaOH] → paste [H2SO4] → [pH1] crude pig cholic acid
Preparation of pig cholic acid products: add 4 times the amount of ethyl acetate to the crude pig cholic acid. Add 150-200g/L activated carbon; heat and flux for 0.5h; cool; filter; add 1.5-2.5 times ethyl acetate to filter cake; combine the filtrates twice. Adding 200g/L anhydrous sodium sulfate, standing overnight, concentrated to the original volume of 1/3, releasing, cooling crystallization, through filtration, washing with ethyl acetate crystallization, drying can obtain pig cholic acid products.
Crude pig cholic acid [ethyl acetate, activated carbon] → filtrate [anhydrous sodium sulfate] → filtrate [concentration] → pig cholic acid products.
|Chemical Properties||white to light beige crystalline powder|
|Uses||Choleretic produced by, and isolated from liver cells.|
|Uses||Cholic Acid is an emulsifier that exists as colorless plates or a white crystalline powder which has a bitter taste with a sweetish aftertaste. it is slightly soluble in water. it functions as an emulsifying agent in egg white.|
|Definition||ChEBI: A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.|
|Purification Methods||This bile acid crystallises from H2O or wet Et2O (as hydrate) or EtOH (as alcoholate). Dry it under vacuum at 94o. When an alcoholic solution of cholic acid + I2 is added to aqueous KI, it forms a molecular compound (C24H40O5I)4 KI. H2O. The methyl ester is dimorphic with m 155o and 162o and  D 20 +25o (EtOH). [Anderson et al. Biochem J 67 323 1957, 85 236 1962, Beilstein 10 III 2162, IV 2071.]|