Dehydrocholic acid CAS 81-23-2

Introduction：Basic information about Dehydrocholic acid CAS 81-23-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Dehydrocholic acid Basic information

• Product Name: Dehydrocholic acid
• Synonyms: 7,12-trioxo-(5-beta)-cholan-24-oicaci;7,12-trioxo-(5beta)-cholan-24-oicaci;Acide dehydrocholique;acidedehydrocholique;Acolen;Atrocholin;Bilidren;Bilostat
• CAS: 81-23-2
• MF: C24H34O5
• MW: 402.53
• EINECS: 201-335-7
• Product Categories: API;APURONE;Inhibitors;Bile Acids;Biochemistry;Steroids;81-23-2
• Mol File: 81-23-2.mol

Dehydrocholic acid Chemical Properties

• Melting point: 238-240 °C
• alpha: 29 º (c=2, dioxane)
• Boiling point: 444.65°C (rough estimate)
• density: 1.0687 (rough estimate)
• vapor pressure: 0.013Pa at 20℃
• refractive index: 30.5 ° (C=2, Dioxane)
• storage temp.: Sealed in dry,Room Temperature
• solubility: ethanol: 10 mg/mL
• pka: pKa 5.12(H2Ot = 20c > CMC) (Uncertain)
• form: Solid
• color: White to Off-White
• biological source: bovine bile synthetic
• Optical Rotation: [α]20/D +26±1°, c =1% in ethanol
• Water Solubility: 65mg/L(30 ºC)
• Merck: 14,2868
• BRN: 3226734
• Major Application: pharmaceutical (small molecule)
• InChIKey: OHXPGWPVLFPUSM-KLRNGDHRSA-N
• SMILES: [H][C@@]12CC(=O)CC[C@]1(C)[C@@]3([H])CC(=O)[C@]4(C)[C@H](CC[C@@]4([H])[C@]3([H])C(=O)C2)[C@H](C)CCC(O)=O
• LogP: 1.64 at 22℃ and pH5.7
• Surface tension: 56.9mN/m at 63mg/L and 20℃
• CAS DataBase Reference: 81-23-2(CAS DataBase Reference)
• NIST Chemistry Reference: Dehydrocholic acid(81-23-2)
• EPA Substance Registry System: Cholan-24-oic acid, 3,7,12-trioxo-, (5.beta.)- (81-23-2)

Safety Information

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: FZ2300000
• TSCA: TSCA listed
• HS Code: 2918300000
• Storage Class: 11 - Combustible Solids

Dehydrocholic acid Usage And Synthesis

Description

Dehydrocholic acid is a semisynthetic bile acid, which is made by the oxidation of cholic acid by chromic acid. It can increase the output of bile by the liver and the filling of the gallbladder. Dehydrocholic acid aids the digestion of fats and increases absorption of fat soluble vitamins.
It is used as a gastrointestinal agent that stimulates the flow of bile into the duodenum (cholagogue) or stimulate the production of bile by the liver (choleretic). It is also used as laxative to relief constipation, diuretic, and a diagnostic aid.

References

[1] Giancarlo Cravotto, Arianna Binello, Luisa Boffa, Ornelio Rosati, Marco Boccalini, Stefano Chimichi (2006) Regio- and stereoselective reductions of dehydrocholic acid, Steroids, 469-475
[2] https://pubchem.ncbi.nlm.nih.gov/compound/dehydrocholic_acid

Chemical Properties

white to off-white amorphous powder

Originator

Dehydrocholic Acid,New ZealandPharmaceuticalsLimited (NZP)

Uses

Dehydrocholic Acid is a derivative of Cholic Acid (C432600). a choleretic produced by, and isolated from liver cells.

Uses

antibacterial

Definition

ChEBI: 3,7,12-trioxo-5beta-cholanic acid is an oxo-5beta-cholanic acid in which three oxo substituents are located at positions 3, 7 and 12 on the cholanic acid skeleton. It has a role as a gastrointestinal drug. It is an oxo-5beta-cholanic acid, a 7-oxo steroid, a 12-oxo steroid and a 3-oxo-5beta-steroid. It is a conjugate acid of a 3,7,12-trioxo-5beta-cholan-24-oate.

Manufacturing Process

A.) Oxidation of cholic acid:
A solution, consisting of 15.40 g of cholic acid and 18.75 g of anhydroussodium acetate in a solvent mixture of 20 ml of ethyl acetate, 30 ml of glacialacetic acid, and 30 ml of water, was prepared. This solution was cooled to20°C. Chlorine gas was bubbled into the solution with vigorous stirring whilethe reaction temperature was maintained at 20°C. The chlorine was deliveredat a constant rate of about 2.5 g per hour over a 4-hour period. The totalamount of chlorine gas was 9.80 g which corresponds to about 3.68 moles permole of cholic acid, or approximately a 23% excess. The solution temperaturewas maintained in the range of 16° to 20°C during the entire addition ofchlorine. Initially the cholic acid solution was very dark-colored. As thereaction progressed, the solution became pale yellow and a precipitate ofsodium chloride deposited. A considerable amount of product and sodiumchloride precipitated during the latter stages of the reaction so that the finalreaction mixture was a heavy slurry which was difficult to stir. After theaddition of chlorine was complete, the slurry was aged one hour with stirringat 20°C. The excess chlorine was then discharged by dropwise addition of10% aqueous sodium sulfite until the solution gave a negative test to starchiodide paper. The semi-crystalline slurry was then diluted with water to raisethe total volume to 225 ml. The water was added dropwise with stirring overa 1-hour period. The ethyl acetate was then distilled off at 65-88°C. Theresulting crystalline slurry was cooled to below 70°C and filtered through asintered-glass funnel of medium porosity. The filter cake was washed until thefiltrate gave a negative halide test with silver nitrate solution and then wassucked partially dry on the funnel. Drying was completed in a drier at 110°Cfor 3 hours. The product was crude pale tan dehydrocholic acid. Yield 14.3(95%); M.P. 225-231°C.
B.) Purification of dehydrocholic acid:
To a chromatographic column, packed with 6.67 g of charcoal ("Nuchar C")with layers of sea sand at either end, 75 ml of acetone was added to wet thecarbon. The column was heated to 40°C, and 25 ml of acetone was drainedoff. A solution of 20 g of dry crude dehydrocholic acid in 500 ml of acetonewas poured into a reservoir atop the column and maintained in this reservoirat 40°C. This solution was then allowed to drop through the column at aconstant rate over a 3-hour period. The column was then washed with 250 mlof acetone flowing through the column at a constant rate over a 1-hour-periodat 40°C. The column effluent and wash acetone were combined andconcentrated to a residual volume of about 100 ml which resulted in theformation of a thick slurry. The slurry was cooled with stirring at 0° to 5°Cand aged for 30 min at this temperature. The slurry was filtered and the filtercake washed with cold acetone. The filter cake of U.S.P. dehydrocholic acidwas sucked partially dry on the filter and then dried at 110°C for 3 hours.Yield 15 g to 17 g (75% to 85%).
A second crop of crystals was obtained from the combined filtrate and washliquid from the first crop filtration. This mixture, which initially had a volumeof about 100 ml, was concentrated to 20 ml. 10 ml of water was added to thesolution and 10 ml of acetone mixed with a small amount of water distilled off.The residual thick slurry of dehydrocholic acid was cooled to 0-5°C, aged at this temperature with stirring for 30 min, and filtered. The filter cake waswashed with acetone at 0°C, partially dried by suction on the filter, and thendried for three hours at 110°C. Yield 1 to 2 g (5% to 10%).

Brand name

Decholin Sodium (Bayer).

Therapeutic Function

Choleretic, Diuretic, Diagnostic aid

Biochem/physiol Actions

Dehydrocholic acid is an oxidation product of cholic acid by chromic acid that is not present in physiological conditions. When used in animal experiments, it stimulates bile secretion.

Dehydrocholic acid Preparation Products And Raw materials

• Raw materials: Ethanol-->Sodium acetate-->Sodium dichromate dihydrate-->bilis extract-->Glycocholic acid-->TAUROCHOLIC ACID-->Cholic acid-->Sodium sulfite-->Tube990-->(5R,7R,8R,9S,10S,13S,14S)-7-hydroxy-10,13-dimethyldodecahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,4H)-dione(WX116145)-->(3R,5S,7R,8R,9S,10S,13S,14S)-3,7-dihydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one(WX116146)-->4,6-ANDROSTADIEN-3,17-DIONE-->Sodium cholate-->(3a,5b,7a,12b)-3,7,12-trihydroxy-Cholan-24-oic acid
• Preparation Products: 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid