81-23-2 Usage
Uses
Used in Gastrointestinal Applications:
Dehydrocholic acid is used as a gastrointestinal agent for its cholagogue and choleretic properties, facilitating bile flow into the duodenum and stimulating bile production by the liver. This helps in the digestion of fats and absorption of fat-soluble vitamins, which is essential for maintaining proper digestive health.
Used in Laxative Applications:
Dehydrocholic acid is utilized as a laxative to provide relief from constipation. Its action promotes bowel movements and helps alleviate the discomfort associated with constipation.
Used in Diuretic Applications:
As a diuretic, dehydrocholic acid increases urine production and helps the body eliminate excess water and salts, which can be beneficial in managing conditions related to fluid retention.
Used in Diagnostic Applications:
Dehydrocholic acid serves as a diagnostic aid in medical procedures, assisting healthcare professionals in identifying and assessing various gastrointestinal conditions.
Used in Antibacterial Applications:
Dehydrocholic acid exhibits antibacterial properties, making it useful in combating bacterial infections and promoting overall health.
Used in Pharmaceutical Industry:
Dehydrocholic acid is used in the pharmaceutical industry as a key ingredient in the development of medications targeting gastrointestinal disorders, constipation relief, and other related health issues. Its multifunctional properties make it a valuable component in the formulation of various therapeutic agents.
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
Originator
Dehydrocholic Acid,New Zealand
Pharmaceuticals
Limited (NZP)
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%).
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.
Check Digit Verification of cas no
The CAS Registry Mumber 81-23-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 1 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 81-23:
(4*8)+(3*1)+(2*2)+(1*3)=42
42 % 10 = 2
So 81-23-2 is a valid CAS Registry Number.
InChI:InChI=1/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/p-1/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1
81-23-2Relevant articles and documents
DIFFERENCE BETWEEN CHOLIC ACID AND CHENODEOXYCHOLIC ACID IN DEPENDENCE UPON CHOLESTEROL OF HEPATIC AND PLASMATIC SOURCES AS THE PRECURSOR IN RATS
Ayaki, Yoshikazu,Ogura, Yoshio,Kitayama, Sayoko,Endo, Sachiko,Ogura, Michio
, p. 509 - 520 (1983)
Some difference in functional pool of cholesterol acting as the precursor of bile acids is pointed out between cholic acid and chenodeoxycholic acid.In order to elucidate this problem further, some experiments were performed with rats equilibrated cholesterol by subcutaneous implantation.The bile duct was cannulated in one series of experiments and ligated in another.After the operation 14C-specific radioactivity of serum cholesterol fell, but reached practically a new equilibrium within three days. 14C-Specific radioactivity of serum cholesterol as well as of biliary bile acids in bile-fistula rats and urinary bile aci ds in bile duct-ligated rats was determined during a three days-period in the new equilibrated state.The results were as follows: (1) 14C-Specific radioactivity of cholic acid and chenodeoxycholic acid in bile was lower than that of serum cholesterol, and 14C-specific radioactivity of cholic acid was clearly lower than that of chenodeoxycholic acid. (2) 14C-Specific radioactivity of cholic acid and β-muricholic acid in urine was lower than that of serum cholesterol, and 14C-specific radioactivity of cholic acid was lower than that of β-muricholic acid. (3) Biliary as well as urinary β-muricholic acid lost tritium label at 7-position entirely during the course of formation from cholesterol.
METHODS FOR PREPARING BILE ACIDS
-
, (2019/02/15)
The present disclosure provides methods of preparing cholic acid, deoxycholic acid, or chenodeoxycholic acid, an ester thereof, or a pharmaceutically or cosmetically acceptable salt thereof, and novel and useful synthetic intermediates, for example, as described for methods 1, 1A, 1B, 2, 3, 3A, and 4. The method can start with a plant derived steroid as a starting material, such as dehydroepiandrosterone (DHEA) or Acetyl-dehydroepiandrosterone (Ac-DHEA). Also provided are pharmaceutical or cosmetic compositions and uses thereof, which comprise one or more of cholic acid, deoxycholic acid, or chenodeoxycholic acid, an ester thereof, or a pharmaceutically or cosmetically acceptable salt thereof, which is of high purity, for example, free of animal derived impurities.
Synthetic method for cholic acid drug 3,7,12-trioxo-5beta-cholanoic acid
-
Paragraph 0013; 0017-0028, (2018/07/30)
The invention discloses a synthetic method for the cholic acid drug 3,7,12-trioxo-5beta-cholanoic acid. The synthetic method comprises the following steps: adding 3,7,12-trimethoxysteroisovaleric acidand a potassium sulfate solution into a reaction vessel, controlling solution temperature, adding cerium nitrate powder in batches, and continuing a reaction; and then adding an isopropyl myristate solution, controlling a stirring speed, continuing the reaction until a white solid is precipitated, washing the white solid with a potassium chloride solution a plurality of times, washing the white solid with a hexyl ether solution a plurality of times, washing the white solid with a cyclohexanone solution a plurality of times, then carrying out recrystallization in a 1,2-epoxypropane solution, and carrying out dehydration with a dehydrating agent so as to obtain the finished 3,7,12-trioxo-5beta-cholanoic acid.
Platinum complexes containing chemically modified bile acids, having antitumor activity
-
Page/Page column 3-4; 6, (2010/02/11)
The present invention relates to platinum complexes containing bile acid derivatives having antitumor activity
Improved enantioselectivity in the epoxidation of cinnamic acid derivatives with dioxiranes from keto bile acids
Bortolini, Olga,Fantin, Giancarlo,Fogagnolo, Marco,Forlani, Roberto,Maietti, Silvia,Pedrini, Paola
, p. 5802 - 5806 (2007/10/03)
The asymmetric epoxidation of substituted cinnamic acids has been obtained in the presence of different keto bile acid derivatives as optically active carbonyl inducers and Oxone as oxygen source. Predominant or almost exclusive formation of both enantiomeric epoxides is obtained (ee up to 95%) depending on the specific substitution at carbons C(7) and C(12) of the bile acid.
Anodic electrochemical oxidation of cholic acid
Medici, Alessandro,Pedrini, Paola,De Battisti, Achille,Fantin, Giancarlo,Fogagnolo, Marco,Guerrini, Alessandra
, p. 63 - 69 (2007/10/03)
Regioselectivity in the anodic electrochemical oxidation of cholic acid with different anodes is described. The oxidation with PbO2 anode affords the dehydrocholic acid in quantitative yield after 22 h. 3α,12α-Dihydroxy-7-oxo-5β-cholan-24-oic acid (59%) and 3α-hydroxy-7,12-dioxo-5β-cholan-24-oic acid (51%) are obtained stopping the reaction at lower time. The rate of the OH-oxidation is C7 > C12 > C3. The electro-oxidation with platinum foil anode gives selectively the 7-ketocholic acid in 40% yield. On the other hand, the graphite plate anode, varying the reaction conditions, produces selectively the dehydrocholic acid in quantitative yield or the 3α,12α-dihydroxy-7-oxo-5β-cholan-24-oic acid (96%) while the 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid (34%) is obtained together with the other oxo acids. Copyright
Regioselective microbial oxidation of bile acids
Fantin, Giancarlo,Ferrarini, Sabina,Medici, Alessandro,Pedrini, Paola,Poli, Silvia
, p. 1937 - 1942 (2007/10/03)
High regioselectivity in the microbial oxidation of C7, C3 and C12 hydroxyl groups of cholic, chenodeoxycholic, deoxycholic and hyocholic acids 1-4 is reported. The tested microrganisms have been isolated from 50 environmental samples withdrawed from an industry that extracts and purify bile acids.
