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Dehydrocholic acid

CAS No.
81-23-2
Chemical Name:
Dehydrocholic acid
Synonyms
DHC;dehydrocholic;Acolen;Atrocholin;Dehydrocholate;3,7,12-trioxo-5β-cholanic acid;5β-CHOLANIC acid-3, 7, 12-TRIONE;Dee-Co;Biochol;Dehycol
CBNumber:
CB0704485
Molecular Formula:
C24H34O5
Molecular Weight:
402.53
MDL Number:
MFCD00066410
MOL File:
81-23-2.mol
MSDS File:
SDS
Last updated:2024-05-20 18:13:44

Dehydrocholic acid 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
form Solid
pka pKa 5.12(H2O t = 20 c > CMC) (Uncertain)
color White to Off-White
Water Solubility 65mg/L(30 ºC)
Merck 14,2868
BRN 3226734
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)
FDA 21 CFR 310.545
FDA UNII NH5000009I
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

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H303
Precautionary statements  P270-P301+P312-P403-P501c
Safety Statements  24/25
WGK Germany  2
RTECS  FZ2300000
TSCA  Yes
HS Code  2918300000
NFPA 704
0
0 0

Dehydrocholic acid price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1166502 Dehydrocholic acid United States Pharmacopeia (USP) Reference Standard 81-23-2 200mg $164.8 2024-03-01 Buy
Cayman Chemical 29176 Dehydrocholic Acid 81-23-2 1g $32 2024-03-01 Buy
Cayman Chemical 29176 Dehydrocholic Acid 81-23-2 5g $93 2024-03-01 Buy
TRC D229340 Dehydrocholic acid 81-23-2 50g $100 2021-12-16 Buy
Biosynth Carbosynth FD11044 Dehydrocholic acid 81-23-2 50g $135.5 2021-12-16 Buy
Product number Packaging Price Buy
1166502 200mg $164.8 Buy
29176 1g $32 Buy
29176 5g $93 Buy
D229340 50g $100 Buy
FD11044 50g $135.5 Buy

Dehydrocholic acid Chemical Properties,Uses,Production

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 Zealand Pharmaceuticals Limited (NZP)

Uses

antibacterial

Uses

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

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 anhydrous sodium acetate in a solvent mixture of 20 ml of ethyl acetate, 30 ml of glacial acetic acid, and 30 ml of water, was prepared. This solution was cooled to 20°C. Chlorine gas was bubbled into the solution with vigorous stirring while the reaction temperature was maintained at 20°C. The chlorine was delivered at a constant rate of about 2.5 g per hour over a 4-hour period. The total amount of chlorine gas was 9.80 g which corresponds to about 3.68 moles per mole of cholic acid, or approximately a 23% excess. The solution temperature was maintained in the range of 16° to 20°C during the entire addition of chlorine. Initially the cholic acid solution was very dark-colored. As the reaction progressed, the solution became pale yellow and a precipitate of sodium chloride deposited. A considerable amount of product and sodium chloride precipitated during the latter stages of the reaction so that the final reaction mixture was a heavy slurry which was difficult to stir. After the addition of chlorine was complete, the slurry was aged one hour with stirring at 20°C. The excess chlorine was then discharged by dropwise addition of 10% aqueous sodium sulfite until the solution gave a negative test to starchiodide paper. The semi-crystalline slurry was then diluted with water to raise the total volume to 225 ml. The water was added dropwise with stirring over a 1-hour period. The ethyl acetate was then distilled off at 65-88°C. The resulting crystalline slurry was cooled to below 70°C and filtered through a sintered-glass funnel of medium porosity. The filter cake was washed until the filtrate gave a negative halide test with silver nitrate solution and then was sucked partially dry on the funnel. Drying was completed in a drier at 110°C for 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 the carbon. The column was heated to 40°C, and 25 ml of acetone was drained off. A solution of 20 g of dry crude dehydrocholic acid in 500 ml of acetone was poured into a reservoir atop the column and maintained in this reservoir at 40°C. This solution was then allowed to drop through the column at a constant rate over a 3-hour period. The column was then washed with 250 ml of acetone flowing through the column at a constant rate over a 1-hour-period at 40°C. The column effluent and wash acetone were combined and concentrated to a residual volume of about 100 ml which resulted in the formation of a thick slurry. The slurry was cooled with stirring at 0° to 5°C and aged for 30 min at this temperature. The slurry was filtered and the filter cake washed with cold acetone. The filter cake of U.S.P. dehydrocholic acid was 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 wash liquid from the first crop filtration. This mixture, which initially had a volume of about 100 ml, was concentrated to 20 ml. 10 ml of water was added to the solution 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 was washed with acetone at 0°C, partially dried by suction on the filter, and then dried 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.

81-25-4
81-23-2
Synthesis of Dehydrocholic acid from Cholic acid
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View Lastest Price from Dehydrocholic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Dehydrocholic Acid pictures 2024-05-27 Dehydrocholic Acid
81-23-2
US $0.00-0.00 / kg 1kg 99% 20tons Sinoway Industrial co., ltd.
Dehydrocholic acid pictures 2024-04-25 Dehydrocholic acid
81-23-2
US $100.00 / kg 1kg 99.80% 20tons Hong Kong Excellence Biotechnology Co., Ltd.
Dehydrocholic acid pictures 2024-04-12 Dehydrocholic acid
81-23-2
US $3.00-1.00 / kg 1kg 99.9% 10 tons Shanghai Aosiris new Material Technology Co., LTD
  • Dehydrocholic acid pictures
  • Dehydrocholic acid
    81-23-2
  • US $100.00 / kg
  • 99.80%
  • Hong Kong Excellence Biotechnology Co., Ltd.
  • Dehydrocholic acid pictures
  • Dehydrocholic acid
    81-23-2
  • US $3.00-1.00 / kg
  • 99.9%
  • Shanghai Aosiris new Material Technology Co., LTD
7,12-trioxo-(5-beta)-cholan-24-oicaci 7,12-trioxo-(5beta)-cholan-24-oicaci Acide dehydrocholique acidedehydrocholique Bilidren Bilostat Biochol Cholagon Cholan DH Cholan-24-oic acid, 3,7,12-trioxo-, (5beta)- Cholepatin Cholic acid, dehydro- Cholimed Chologon Chololin Decholin Dee-Co Dehychol Dehycol Dehycon Dehydrocholsaeure Dehystolin Deidrocolico Vita 5β-Cholanic acid-3,5,12-trione 3,7,12-Triketocholanic acid~3,7,12-Trioxo-5-beta-cholan-24-oic acid dehydrocholic acid free acid*crystalline kehydrocholic acid Dehydrocholicacid,99% 3,7,12-trioxo-5-á-cholan-24-oic acid DEHYDROCHOLICACID,USP DEHYDROCHOLIC ACID(RG) deidrocolicovita Didocol Didrocolo Dilabil Dilahil Doxycholpotassium Drenobyl Erebile Felacrinos Hykolex Ketochol Khologon Novocolin Oxycholin Procholon Sanocholen Triketocholanic acid triketocholanicacid TRIKETOCHOLANIC KETOCHOLANIC ACID DEHYDROCHOLIC ACID 3,7,12-Triketo-5beta-cholanic acid 3,7,12-Triketo-5beta-cholanoic acid 3,7,12-Triketocholanic acid 3,7,12-triketocholanicacid 3,7,12-Triketocholic acid 3,7,12-Trioxo-24-cholanic acid