474-25-9 Usage
Description
Chenodeoxycholic acid is a bile acid synthesized in the liver from cholesterol. It is a hydrophobic primary bile acid that activates nuclear receptors involved in cholesterol metabolism. Chenodeoxycholic acid is the first agent to be introduced into the US market for the treatment of radiolucent gallstones and is the 7α-isomer of ursodeoxycholic acid.
Uses
Used in Medical Therapy:
Chenodeoxycholic acid is used as a therapeutic agent for dissolving gallstones. It reduces the biliary concentration of cholesterol relative to that of bile acids and phospholipid, reducing the saturation and thus the lithogenicity of the bile. Success rates in dissolving gallstones are in the range of 50-70% within 4-24 months of treatment.
Used in Treatment of Cerebrotendinous Xanthomatosis (CTX):
Chenodeoxycholic acid is used as a long-term replacement therapy for CTX, a rare genetic disorder that affects the nervous system and causes the accumulation of cholesterol in various tissues.
Used in Investigation of Small-Intestinal Absorption:
Chenodeoxycholic acid has been used in a study to investigate its effects on the small-intestinal absorption of bile acids in patients with ileostomies.
Used in Apoptosis Induction:
Chenodeoxycholic acid is used as an apoptosis inducer via protein kinase C (PKC)-dependent signaling pathways. It is a major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate.
Used in Solubilization and Transport of Dietary Lipids:
Chenodeoxycholic acid, along with other bile acids, forms mixed micelles with lecithin in bile, which solubilize cholesterol and facilitate its excretion. It also facilitates fat absorption in the small intestine by micellar solubilization of fatty acids and monoglycerides.
Used in Dye Solar Cells:
Chenodeoxycholic acid is used as a staining additive, commonly used with ruthenium or organic photo-sensitizers in the preparation of staining solutions for dye solar cells. This co-adsorbent prevents dye aggregation on the semiconductor surface, reducing losses in the solar cell's operation.
Used in Supramolecular Chemistry:
Chenodeoxycholic acid acts as a urea receptor in supramolecular chemistry, which can contain anions.
Used in Treatment of Constipation:
Chenodeoxycholic acid is used to treat constipation and cerebrotendineous xanthomatosis.
Used in Regulation of Genes Involved in Lipid Metabolism:
Chenodeoxycholic acid is a physiological ligand for farnesoid X receptor (FXR), a nuclear receptor that regulates genes involved in lipid metabolism. Bile acid-controlled signaling pathways are promising novel targets to treat metabolic diseases such as obesity, type II diabetes, hyperlipidemia, and atherosclerosis.
Chemical Properties:
Chenodeoxycholic acid is an off-white solid and is available under the brand name CHEWM.
Originator
Rowell (USA)
History
Chenodeoxycholic acid was isolated in 1924 from goose gall by Adolf Windaus and human gall by Heinrich Wieland.Its complete structural configuation was elucidated by Hans Lettre at the University of Gottingen.
In 1968, William Admirand and Donald Small at Boston University Medical School established that in patients with gallstones their bile was saturated with cholesterol, sometimes even exhibiting microcrystals, whereas this was not the case in normal people.It was then found that biliary levels of cholic acid and chenodeoxycholic acid were lower in patients with cholesterol gallstones than in normal people. Leslie Thistle and John Schoenfield at the Mayo Clinic in Rochester, Minnesota, then administered individual bile salts by mouth for four months and found that chenodeoxycholic acid reduced the amount of cholesterol in the bile.This led to a national collaborative study in the United States, which confirmed the effectiveness of chenodeoxycholic acid in bringing about dissolution of gallstones in selected patients. However, recent developments such as laparoscopic cholecystectomy and endoscopic biliary techniques have curtailed the role of chenodeoxycholic acid and ursodeoxycholic acid in the treatment of cholelithiasis.
Manufacturing Process
To 1,400 ml of an approximately 50% water/triglycol solution of the
potassium salt of chenodeoxycholic acid, obtained by the Wolff-Kishner
reduction (using hydrazine hydrate and potassium hydroxide) from 50 g of 7-
acetyl-12-ketochenodeoxycholic acid, 220 ml of dilute hydrochloric acid is
added to bring the pH to 2. The solution is stirred and the crude
chenodeoxycholic acid precipitates. The precipitate is recovered and dried to
constant weight at about 60°C. About 36 g of the crude chenodeoxycholic
acid, melting in the range of 126°-129°C, is obtained.
25 g of crude chenodeoxycholic acid so obtained is dissolved in 750 ml of
acetonitrile while stirring and heating. 3 g of activated charcoal is added and
then removed by suction filtering. The resulting liquid filtrate is cooled, the
pure chenodeoxycholic acid crystallizing out. The crystals are recovered by
suction filtering and the recovered crystals dried under vacuum. The yield is
19 g of pure chenodeoxycholic acid with a melting range of 168°-171°C.
Therapeutic Function
Gallostone dissolving agent
World Health Organization (WHO)
Chenodeoxycholic acid was introduced in 1975 for the treatment
of cholelithiasis. It is available in several countries and the World Health
Organization is not aware that registration has been refused in any other country.
Flammability and Explosibility
Nonflammable
Purification Methods
This major bile acid in vertebrates (~80mg) is chromatographed on silica gel (5g) and eluted with CHCl3/EtOAc (3:2) and crystallised from EtOAc/hexane. It has IR: max 1705 cm-1(CHCl3). It also crystallises from EtOAc, EtOAc/heptane after purifying via the poorly soluble Na and K salt if necessary. [Kametani et al. J Org Chem 4 7 2331 1982, Beilstein 10 IV 1604.]
Check Digit Verification of cas no
The CAS Registry Mumber 474-25-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 4 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 474-25:
(5*4)+(4*7)+(3*4)+(2*2)+(1*5)=69
69 % 10 = 9
So 474-25-9 is a valid CAS Registry Number.
InChI:InChI=1/C24H40O5/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/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22?,23+,24-/m1/s1
474-25-9Relevant articles and documents
Solvolysis of chenodeoxycholic acid sulfates
Cohen,Budai,Javitt
, p. 621 - 626 (1981)
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Preparation method of chenodeoxycholic acid
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, (2021/01/24)
The invention relates to the technical field of medicine synthesis, in particular to a preparation method of chenodeoxycholic acid. The invention develops a method for synthesizing the chenodeoxycholic acid by taking hyodeoxycholic acid(3alpha, 6alpha-dihydroxy-5beta-cholanic acid)as a raw material through nine steps of reaction, the reaction conditions of each step are mild, the control is easy,the process is simple, the used raw materials are wide in source, low in price and easy to obtain, the yield is high, the total yield can reach 61%, the synthesis cost is low, and the method is suitable for mass preparation and industrial production.
Preparation method and application of seal cholic acid
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, (2021/02/10)
The invention provides a method for selectively separating seal cholic acid from a duck bile extract, which facilitates the utilization of the seal cholic acid which is an important biological resource in the duck bile. The invention also provides a method for preparing chenodeoxycholic acid from the seal cholic acid. Therefore, the problem of insufficient supply of chenodeoxycholic acid raw materials can be alleviated, improved. and meanwhile, corresponding biological waste pollution is also avoided. The method is easy for industrial production and has very good economic value and applicationprospect.
Method for synthesizing 3alpha, 7alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid
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Paragraph 0013, (2021/02/06)
The invention belongs to the field of organic synthesis of carbocyclic compounds, and particularly relates to a method for synthesizing 3alpha, 7alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid. According to the method, chenodeoxycholic acid with purity of 97.6% is synthesized by using duck cholic acid as a raw material. The comprehensive yield is 87.8%, the purity of the product is highwhile a high-temperature reaction is avoided, and later impurity removal is simple and convenient.