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Chenodeoxycholic acid

Chenodeoxycholic acid Structure
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
MOL File:
474-25-9.mol
MSDS File:
SDS
Modify Date:
2024/8/2 18:12:07

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)
EPA Substance Registry System Chenodiol (474-25-9)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
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(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) C9377 Chenodeoxycholic acid 474-25-9 5G ₹18976.23 2022-06-14 Buy
TCI Chemicals (India) C0750 Chenodeoxycholic Acid min. 97.0 % 474-25-9 5G ₹4400 2022-05-26 Buy
TCI Chemicals (India) C0750 Chenodeoxycholic Acid min. 97.0 % 474-25-9 25G ₹11800 2022-05-26 Buy
ottokemi C 1903 Chenodeoxycholic acid 98% 474-25-9 100mg ₹2205 2022-05-26 Buy
ottokemi C 1903 Chenodeoxycholic acid 98% 474-25-9 500mg ₹4095 2022-05-26 Buy
Product number Packaging Price Buy
C9377 5G ₹18976.23 Buy
C0750 5G ₹4400 Buy
C0750 25G ₹11800 Buy
C 1903 100mg ₹2205 Buy
C 1903 500mg ₹4095 Buy

Chenodeoxycholic acid Chemical Properties,Uses,Production

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

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

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.

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.

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.]

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