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Chenodeoxycholic acid

CAS No.
474-25-9
Chemical Name:
Chenodeoxycholic acid
Synonyms
CDCA;CHENODIOL;CHENODEOXYCHOLATE;3ALPHA,7ALPHA-DIHYDROXY-5BETA-CHOLANIC ACID;Chenix;ChenodeoxychoL;3a,7a-Dihydroxy-5b-cholanoic acid;Fluibil;Kebilis;chendol
CBNumber:
CB4285737
Molecular Formula:
C24H40O4
Molecular Weight:
392.57
MDL Number:
MFCD00064142
MOL File:
474-25-9.mol
MSDS File:
SDS
Last updated:2024-01-02 15:08:22

Chenodeoxycholic acid Properties

Melting point 165-167 °C (lit.)
Boiling point 437.26°C (rough estimate)
alpha 12 º (c=1, CHCl3)
Density 0.9985 (rough estimate)
refractive index 1.4460 (estimate)
Flash point 9℃
storage temp. room temp
solubility PRACTICALLY INSOLUBLE
form Powder
pka pKa 4.34 (Uncertain)
color White to off-white
Water Solubility PRACTICALLY INSOLUBLE
Merck 13,2062
BRN 3219887
InChIKey RUDATBOHQWOJDD-BSWAIDMHSA-N
LogP 3.05 at 20℃
CAS DataBase Reference 474-25-9(CAS DataBase Reference)
FDA UNII 0GEI24LG0J
Proposition 65 List Chenodiol
ATC code A05AA01
EPA Substance Registry System Chenodiol (474-25-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
Hazard Codes  Xn
Risk Statements  63
Safety Statements  22-24/25-45-36/37
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  2
RTECS  FZ1980000
HS Code  29181990
NFPA 704
3
0 0

Chenodeoxycholic acid price More Price(45)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C9377 Chenodeoxycholic acid ≥97% 474-25-9 5g $184 2024-03-01 Buy
Sigma-Aldrich C9377 Chenodeoxycholic acid ≥97% 474-25-9 25g $414 2024-03-01 Buy
Alfa Aesar J60364 Chenodeoxycholic acid 474-25-9 5g $83.9 2023-06-20 Buy
Alfa Aesar J60364 Chenodeoxycholic acid 474-25-9 25g $252 2023-06-20 Buy
Cayman Chemical 10011286 Chenodeoxycholic Acid ≥95% 474-25-9 1g $32 2024-03-01 Buy
Product number Packaging Price Buy
C9377 5g $184 Buy
C9377 25g $414 Buy
J60364 5g $83.9 Buy
J60364 25g $252 Buy
10011286 1g $32 Buy

Chenodeoxycholic acid Chemical Properties,Uses,Production

Uses

Chenodeoxycholic acid is a bile acid synthesized in the liver from cholesterol. henodeoxycholic acid has been used in a study to assess its effects as a long-term replacement therapy for cerebrotendinous xanthomatosis (CTX). It has also been used in a study to investigate its effects on the small-intestinal absorption of bile acids in patients with ileostomies.

Description

Chenodeoxycholic acid is the first agent to be introduced into the US market for the treatment of radiolucent gallstones. Large scale clinical trials have demonstrated the safety and efficacy of this agent. Chenodeoxycholic acid 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. Continuation of the drug after stone dissolution may be required to prevent reoccurrence. Chenodeoxycholic acid is the 7α-isomer of ursodeoxycholic acid which was introduced into the European market in 1978.
chenodeoxycholic acid structure
chenodeoxycholic acid structure

Chemical Properties

Off-White Solid

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.

Uses

An apoptosis inducer via PKC-dependent signalling pathway.

Uses

anticholithogenic, antilipemic agent

Uses

A major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus fa cilitates its excretion. Fcilitates fat absorption in the small intestine by micellar solubilization of fatty acids and monoglycerides. Anticholelithogenic. Epimeric with Ursodiol.

Uses

Chenodeoxycholic acid is a bile acid that induces apoptosis through protein kinase C signaling pathways.It is a major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus facilitates its excretion.Bile acids are essential for solubilization and transport of dietary lipids, are the major products of cholesterol catabolism, and are physiological ligands for farnesoid X receptor (FXR), a nuclear receptor that regulates genes involved in lipid metabolism.They are also inherently cytotoxic, as physiological imbalance contributes to increased oxidative stress. Bile acid-controlled signaling pathways are promising novel targets to treat such metabolic diseases as obesity, type II diabetes, hyperlipidemia, and atherosclerosis.

  1. Chenodeoxycholic acid is widely utilized in therapeutic applications. It is applied in medical therapy to dissolve gallstones. It is employed in the treatment of cerebrotendineous xanthomatosis. It is used to treat constipation and cerebrotendineous xanthomatosis. It acts as a urea receptor in supramolecular chemistry which can contain anions. It is a staining additive commonly used with ruthenium or organic photo-sensitizers in the preparation of staining solutions for dye solar cells.
  2. Chenodeoxycholic Acid is a staining additive commonly used with ruthenium or organic photo-sensitizers in the preparation of staining solutions for Dye Solar Cells. This co-adsorbent will prevent dye aggregation on the semiconductor surface, reducing losses in the solar cell's operation.
  3. Chenodeoxycholic Acid is a white solid added with the dye powder to the solvent while preparing staining solutions. The concentration of co-adsorbent is typically 10 fold the dye concentration.
  4. Chenodeoxycholic acid has been used in a study to assess its effects as a long-term replacement therapy for cerebrotendinous xanthomatosis (CTX).
  5. It has also been used in a study to investigate its effects on the small-intestinal absorption of bile acids in patients with ileostomies.
  6. Chenodeoxycholic acid (CDCA) is a hydrophobic primary bile acid that activates nuclear receptors involved in cholesterol metabolism.EC50 concentrations for activation of FXR range from 13-34 μM.In cells, CDCA also binds to bile acid binding proteins (BABP) with a reported stoichiometry of 1:2.CDCA toxicity is linked to increased cellular glutathione levels and increased oxidative stress. Exposure of cells to excess CDCA contributes to liver and intestinal cancers.

Definition

ChEBI: Chenodeoxycholic acid is a dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively. It has a role as a human metabolite and a mouse metabolite. It is a bile acid, a dihydroxy-5beta-cholanic acid and a C24-steroid. It is a conjugate acid of a chenodeoxycholate.

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.

brand name

CHEWM

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.

General Description

Chenodeoxycholic acid is a bile acid synthesized in the liver from cholesterol.

Flammability and Explosibility

Non flammable

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.]

19684-68-5
474-25-9
Synthesis of Chenodeoxycholic acid from Cholan-24-oic acid, 3-(acetyloxy)-7-hydroxy-, methyl ester, (3α,5β,7α)-
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View Lastest Price from Chenodeoxycholic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Chenodeoxycholic acid pictures 2024-03-29 Chenodeoxycholic acid
474-25-9
US $98.00-90.00 / kilograms 1kilograms 99% 200tons Hebei Dangtong Import and export Co LTD
Chenodeoxycholic Acid pictures 2024-03-26 Chenodeoxycholic Acid
474-25-9
US $85.00-45.00 / Kg/Bag 1Kg/Bag 0.90 20 tons Sinoway Industrial co., ltd.
Chenodeoxycholic acid pictures 2024-03-16 Chenodeoxycholic acid
474-25-9
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Chenocedon Chenocol Chenodex Chenofalk Chenossil Cholan-24-oic acid, 3,7-dihydroxy-, (3α,5β,7α)- Cholanorm Fluibil Hekbilin Kebilis Ulmenide 5-BETA-CHOLAN-24-OICACID,3-ALPHA,7-ALPHA-DIHYDROXY- 3a,7a-Dihydroxy-5β-cholanic acid 5β-Cholanic acid-3a,7a-diol Chenodoxycholic acid CHENODEOXYCHOLIC ACID CRYSTALLINE CHENODEOXYCHOLIC ACID :CHOLAN-24-OICACID, 3,7-DIHYDROXY-, (3A,5B,7A)-, ChenodeoxycholicAcidCp9598%Min CHENODEXOXYCHOLICACID (4R)-4-[(3R,5S,7R,8S,9S,10R,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4] 5BETA-CHOLANIC ACID-3ALPHA,7ALPHA-DIOL 5BETA-CHOLANIC ACID-3,7-DIOL 5B-CHOLANIC ACID-3A,7A-DIOL (3a,5,7a)-3,7-Dihydroxycholan-24-oic Acid 17-(1-Methyl-3-carboxypropyl)etiocholane-3a,7a-diol URSODEOXYCHOLOC ACID 3,7-dihydroxy-,(3-alpha,5-beta,7-alpha)-cholan-24-oicaci 3,7-dihydroxy-,(3alpha,5beta,7alpha)-cholan-24-oicaci 3,7-Dihydroxy-5-Cholanicacid 3-alpha,7-alpha-dihydroxy-5-beta-cholan-24-oicaci 3-alpha,7-alpha-dihydroxy-5-beta-cholan-24-oicacid 3-alpha,7-alpha-dihydroxycholanicacid 3-alpha,7-alpha-dihydroxycholansaeure 7-alpha-hydroxylithocholicacid anthropodeoxycholicacid anthropodesoxycholicacid anthropododesoxycholicacid chendol chenicacid chenodesoxycholsaeure gallodesoxycholicacid 17b-(1-Methyl-3-carboxypropyl)etiocholane-3a,7a-diol 7a-Hydroxylithocholic acid Chendiol Chenodeoxycholic acid,98% Chenodeoxycholic acid,3α,7α-Dihydroxy-5β-cholanic acid, 5β-Cholanic acid-3α,7α-diol, Chenodiol Chenodeoxycholic acid, 98% 5GR (3α,5β,7α)-3,7-Dihydroxycholan-24-oic Acid 5beta-Cholanic Acid-3alpha,7alpha-diol 3alpha,7alpha-Dihydroxy-5beta-cholanic Acid 3α,7α-dehydroxy-5βcholanic acid Ursodeoxycholic Acid IMpurity A 3α,7α-Dihydroxy-5β-cholanic acid, 5β-Cholanic acid-3α,7α-diol, Chenodiol Chenodeoxycholic acid,Chenodiol,CDCA (R)-4-((3R,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid (R)-4-((3R,5S,7R,10S,13R)-3,7-dihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid URSODEOXYCHOLOC ACID,3,7-dihydroxy-,(3-alpha,5-beta,7-alpha)-cholan-24-oicaci 5β-Cholanic acid-3α,7α-diol Chenodiol CHENODEOXYCHOLIC ACID