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81-25-4

81-25-4 Structure

81-25-4 Structure
IdentificationMore
[Name]

Cholic acid
[CAS]

81-25-4
[Synonyms]

3,7,12-TRIHYDROXYCHOLANIC ACID
3A,7A,12A-TRIHYDROXY-5B-CHOLAN-24-OIC ACID
3ALPHA,7ALPHA,12ALPHA-TRIHYDROXY-5BETA-CHOLAN-24-IC ACID
3ALPHA,7ALPHA,12ALPHA-TRIHYDROXY-5BETA-CHOLAN-24-OIC ACID
3ALPHA, 7ALPHA, 12ALPHA-TRIHYDROXY-5BETA-CHOLANIC ACID
5-BETA-CHOLANIC ACID-3-ALPHA, 7-ALPHA, 12-ALPHA-TRIOL
7-ALPHA,8-ALPHA,12-ALPHA-TRIHYDROXY-5-BETA-CHOLAN-24-OIC ACID
CA
CHOLALIC ACID
CHOLALIN
cholan-24-oic acid
CHOLAN-24-OIC ACID, 3,7,12-TRIHYDROXY-, (3,5,7,12)-
CHOLIC ACID
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)-
12α-Trihydroxy-5β-cholan-24-oic acid.
3α,7α,12α-Trihydroxy-5α-cholanic acid,
Cholic acd
Cyclosphorine
[EINECS(EC#)]

201-337-8
[Molecular Formula]

C24H40O5
[MDL Number]

MFCD00003672
[Molecular Weight]

408.57
[MOL File]

81-25-4.mol
Chemical PropertiesBack Directory
[Appearance]

white to light beige crystalline powder
[mp ]

200-201 °C(lit.)
[alpha ]

36 º (c=0.6, 95% EtOH)
[storage temp. ]

Store at RT.
[solubility ]

methanol: 0.1 g/mL, clear
[Water Solubility ]

0.28 g/L (15 ºC)
[Merck ]

14,2203
[Detection Methods]

Chromatography, colorimetry
[BRN ]

2822009
[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.
[CAS DataBase Reference]

81-25-4(CAS DataBase Reference)
[NIST Chemistry Reference]

Cholic acid(81-25-4)
[EPA Substance Registry System]

81-25-4(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

2
[RTECS ]

FZ9350000
[HS Code ]

29181990
[Hazardous Substances Data]

81-25-4(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Etanol-->Ethyl acetate-->Sulfuric acid -->Taurine-->HYOCHOLIC ACID
[Preparation Products]

Atificial Cow-bezoar-->Glycocholic acid
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid(81-25-4).msds
Questions And AnswerBack Directory
[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.
[Uses]

(1) Emulsifiers.
(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).
[Toxicity]

ADI O~1.25mg/kg(FAO/WH0,2001)。
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.
Spectrum DetailBack Directory
[Spectrum Detail]

Cholic acid(81-25-4)IR1
Cholic acid(81-25-4)IR2
Cholic acid(81-25-4)Raman
Cholic acid(81-25-4)13CNMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Cholic acid, 97%(81-25-4)
[Alfa Aesar]

Cholic acid, 98+%(81-25-4)
[Sigma Aldrich]

81-25-4(sigmaaldrich)
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