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Top quality Chenodeoxycholic acid 99%
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474-25-9 Usage

Uses

An apoptosis inducer via PKC-dependent signalling pathway.

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

Therapeutic Function

Gallostone dissolving agent

Uses

anticholithogenic, antilipemic agent

Chemical Properties

Off-White Solid

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.

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.

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.

Brand name

CHEWM

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.

Originator

Rowell (USA)

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.]

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. 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. 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. 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. Chenodeoxycholic 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. 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.

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.
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

474-25-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (C0750)  Chenodeoxycholic Acid  >97.0%(GC) 474-25-9 5g 860.00CNY Detail
TCI America (C0750)  Chenodeoxycholic Acid  >97.0%(GC) 474-25-9 25g 2,690.00CNY Detail
Sigma-Aldrich (C1050000)  Chenodeoxycholic acid  European Pharmacopoeia (EP) Reference Standard 474-25-9 C1050000 1,880.19CNY Detail
Sigma (C9377)  Chenodeoxycholic acid  ≥97% 474-25-9 C9377-100MG 341.64CNY Detail
Sigma (C9377)  Chenodeoxycholic acid  ≥97% 474-25-9 C9377-5G 919.62CNY Detail
Sigma (C9377)  Chenodeoxycholic acid  ≥97% 474-25-9 C9377-25G 3,511.17CNY Detail

474-25-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name chenodeoxycholic acid

1.2 Other means of identification

Product number -
Other names CDCA

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:474-25-9 SDS

474-25-9Synthetic route

3α,7α-Dihydroxy-chol-11-ensaeure

3α,7α-Dihydroxy-chol-11-ensaeure

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 70℃; under 30003 Torr; for 12h;99%
(4R)-methyl 4-((3R,5R,7R,10S,13R,17R)-3-acetoxy-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
19684-68-5

(4R)-methyl 4-((3R,5R,7R,10S,13R,17R)-3-acetoxy-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol for 1h; Reflux;97%
With water; sodium hydroxide In methanol; water for 2h; Reagent/catalyst; Reflux;97%
With sodium hydroxide In tetrahydrofuran; methanol; water at 70℃; for 3h;95%
7-Ketolithocholic acid
4651-67-6

7-Ketolithocholic acid

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
Stage #1: 7-Ketolithocholic acid With potassium tert-butylate; palladium(II) hydroxide; potassium hydroxide In isopropyl alcohol at 20℃; for 0.166667h;
Stage #2: With hydrogen In isopropyl alcohol at 40 - 80℃; Reagent/catalyst; Temperature;
A n/a
B 95%
With sodium tetrahydroborate; sodium hydrogencarbonate In water at 20℃; for 0.5h; var. reducing agents;A 94%
B 2%
With potassium In tert-butyl alcohol for 0.5h; Heating; var. reducing agents;A 6%
B 94%
7-Ketolithocholic acid
4651-67-6

7-Ketolithocholic acid

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 2h;93%
(4R)-methyl 4-((3R,5S,7R,10S,13R,17R)-7-acetoxy-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
93701-16-7

(4R)-methyl 4-((3R,5S,7R,10S,13R,17R)-7-acetoxy-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol for 6h; Reflux;90.9%
3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid
2458-08-4

3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With potassium hydroxide; hydrazine In 2-methoxy-ethanol; water at 110 - 135℃; for 12h; Wolff-Kishner reduction;90%
With potassium hydroxide; ethylene glycol weiteres Reagens: N2H4;
With potassium hydroxide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol weiteres Reagens: N2H4;
methyl 3α,7α-diacetoxy-5β-cholan-24-oate
2616-71-9

methyl 3α,7α-diacetoxy-5β-cholan-24-oate

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
Stage #1: methyl 3α,7α-diacetoxy-5β-cholan-24-oate With sodium hydroxide In dichloromethane at 20 - 30℃; for 1h;
Stage #2: With sulfuric acid
87.8%
In methanol; isopropyl alcohol reflux 4 h then RT;69%
With potassium hydroxide
methyl 3α,7α-diacetoxy-12-one-5β-cholest-24-carboxylate
28535-81-1

methyl 3α,7α-diacetoxy-12-one-5β-cholest-24-carboxylate

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With hydrazine hydrate; potassium hydroxide In ethylene glycol at 120 - 210℃; for 5h;86.6%
With sodium ethanolate; hydrazine hydrate at 160℃;
With hydrazine hydrate; potassium hydroxide In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 120 - 210℃; for 4h; Wolff-Kishner Reduction; Large scale;
Stage #1: methyl 3α,7α-diacetoxy-12-one-5β-cholest-24-carboxylate With hydrazine hydrate; potassium hydroxide In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 120℃; for 2h;
Stage #2: at 210℃; for 3h;
Multi-step reaction with 2 steps
1: Alkaline conditions
View Scheme
ethyl 3α-benzoyloxy-7α-hydroxy-chol-5-en-24-oate

ethyl 3α-benzoyloxy-7α-hydroxy-chol-5-en-24-oate

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
Stage #1: ethyl 3α-benzoyloxy-7α-hydroxy-chol-5-en-24-oate With palladium 10% on activated carbon; hydrogen; acetic acid In ethanol under 2844.39 Torr; for 24h;
Stage #2: With methanol; sodium hydroxide for 18h; Reflux;
82%
C29H48O5

C29H48O5

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 80℃; for 4h;30%
ethyl chenodeoxycholate acid 7-acetate

ethyl chenodeoxycholate acid 7-acetate

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 75℃; for 6h;28%
C29H46O5

C29H46O5

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 75℃; for 5h;28%
C33H48O5

C33H48O5

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 60℃; for 8h;26%
3,7-diketocholanic acid
859-97-2

3,7-diketocholanic acid

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With ethanol; platinum Hydrogenation;
With acetic acid; platinum Hydrogenation;
With sodium tetrahydroborate; water; sodium hydroxide
3,7-diketocholanic acid
859-97-2

3,7-diketocholanic acid

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With aluminum isopropoxide; isopropyl alcohol
7-Ketolithocholic acid
4651-67-6

7-Ketolithocholic acid

sodium ethanolate
141-52-6

sodium ethanolate

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
at 200℃;
methyl 3α-hydroxy-7α-acetoxy-12-oxocholanate
71837-87-1

methyl 3α-hydroxy-7α-acetoxy-12-oxocholanate

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With potassium hydroxide; ethylene glycol weiteres Reagens: N2H4;
With potassium hydroxide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol weiteres Reagens: N2H4;
3,7-diketocholanic acid
859-97-2

3,7-diketocholanic acid

aluminum isopropoxide
555-31-7

aluminum isopropoxide

isopropyl alcohol
67-63-0

isopropyl alcohol

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

3α,7α-dihydroxy-12-oxocholanic acid tosylhydrazone
79580-95-3

3α,7α-dihydroxy-12-oxocholanic acid tosylhydrazone

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With sodium tetrahydroborate In acetic acid for 3h; Ambient temperature;
7-hydroxy-3-(sulfooxy)-(3α,5β,7α)-cholan-24-oic acid
64520-49-6, 68780-68-7, 68780-73-4, 68833-02-3, 124815-69-6, 59132-32-0

7-hydroxy-3-(sulfooxy)-(3α,5β,7α)-cholan-24-oic acid

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol; acetone at 37℃; for 18h; Product distribution; solvolyse methods, var. of temp., solvent, reagent and time;
chenodeoxycholic acid 7-sulfate
59132-31-9

chenodeoxycholic acid 7-sulfate

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With hydrogenchloride; 2,2-dimethoxy-propane In methanol; ethyl acetate at 25℃; for 24h; Product distribution; solvolyse methods, var. of temp., solvent, reagent and time;
Conditions
ConditionsYield
With acetate buffer; glycyrrhizinic acid hydrolase at 45℃; hydrolysis; other enzyme (β-glucuronidase);
(25RS)-3α,7α-dihydroxy-5β-cholestan-26-oic acid
17974-66-2

(25RS)-3α,7α-dihydroxy-5β-cholestan-26-oic acid

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
rat liver homogenate, NAD, pH=8.5;
3α,7α,24-trihydroxy-5β-cholestan-26-oic acid

3α,7α,24-trihydroxy-5β-cholestan-26-oic acid

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
rat liver homogenate, NAD, pH=8.5;
(E)-(R)-6-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-2-methyl-hept-2-enoic acid

(E)-(R)-6-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-2-methyl-hept-2-enoic acid

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
rat liver homogenate, NAD, pH=8.5;
6A,6C-bis(2-naphthylsulfonyl)-γ-cyclodextrin chenodeoxycholic acid 1:1 complex

6A,6C-bis(2-naphthylsulfonyl)-γ-cyclodextrin chenodeoxycholic acid 1:1 complex

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

6A,6C-bis(2-naphthylsulfonyl)-γ-cyclodextrin

6A,6C-bis(2-naphthylsulfonyl)-γ-cyclodextrin

Conditions
ConditionsYield
In water; ethylene glycol at 25℃; Equilibrium constant; decomplexation;
6A,6D-bis(2-naphthylsulfonyl)-γ-cyclodextrin chenodeoxycholic acid 1:1 complex

6A,6D-bis(2-naphthylsulfonyl)-γ-cyclodextrin chenodeoxycholic acid 1:1 complex

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

6A,6D-bis(2-naphthylsulfonyl)-γ-cyclodextrin

6A,6D-bis(2-naphthylsulfonyl)-γ-cyclodextrin

Conditions
ConditionsYield
In water; ethylene glycol at 25℃; Equilibrium constant; decomplexation;
6A,6E-bis(2-naphthylsulfonyl)-γ-cyclodextrin chenodeoxycholic acid 1:1 complex

6A,6E-bis(2-naphthylsulfonyl)-γ-cyclodextrin chenodeoxycholic acid 1:1 complex

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

6A,6E-bis(2-naphthylsulfonyl)-γ-cyclodextrin

6A,6E-bis(2-naphthylsulfonyl)-γ-cyclodextrin

Conditions
ConditionsYield
In water; ethylene glycol at 25℃; Equilibrium constant; decomplexation;
3α,7α-diacetoxy-12-oxo-5β-cholan-24-oic acid methyl ester

3α,7α-diacetoxy-12-oxo-5β-cholan-24-oic acid methyl ester

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With potassium hydroxide; ethylene glycol weiteres Reagens: N2H4;
With potassium hydroxide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol weiteres Reagens: N2H4;
methanol
67-56-1

methanol

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

chenodeoxycholic acid methyl ester
3057-04-3

chenodeoxycholic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride100%
With toluene-4-sulfonic acid at 20℃; for 1h;100%
With toluene-4-sulfonic acid for 2h; Reflux; Inert atmosphere;100%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

Dehydrochenodeoxycholic acid
4185-00-6

Dehydrochenodeoxycholic acid

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; D-glucose; Pseudomonas paucimobilis; yeast extracxt; peptone In water at 28℃; for 24h;100%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

chenodeoxycholic acid methyl ester
3057-04-3

chenodeoxycholic acid methyl ester

Conditions
ConditionsYield
In methanol; hexane; toluene at 20℃;100%
N-Methyltaurine
107-68-6

N-Methyltaurine

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

3α,7α-dihydroxy-5β-cholan-24-oyl-N-methyltaurine
93790-68-2

3α,7α-dihydroxy-5β-cholan-24-oyl-N-methyltaurine

Conditions
ConditionsYield
With triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In N,N-dimethyl-formamide at 20℃; for 1h;100%
methanol
67-56-1

methanol

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

C26H44O4

C26H44O4

Conditions
ConditionsYield
100%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

acetic anhydride
108-24-7

acetic anhydride

3α,7α-diacetoxy-24-phenyl-5β-cholan-24-oic acid
33628-52-3

3α,7α-diacetoxy-24-phenyl-5β-cholan-24-oic acid

Conditions
ConditionsYield
With pyridine at 20℃; for 24h;99%
With pyridine at 20℃; for 3h;97%
With pyridine at 20℃; for 15h;95%
ethanol
64-17-5

ethanol

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

ethyl 3α,7α-dihydroxy-5β-cholan-24-oate

ethyl 3α,7α-dihydroxy-5β-cholan-24-oate

Conditions
ConditionsYield
With Candida antarctica lipase B In hexane at 55℃; for 24h; Reagent/catalyst; Solvent; Temperature; Time; Enzymatic reaction;99%
With heterologous Rhizopus oryzae lipase immobilized on Octadecyl Sepabeads In di-isopropyl ether at 55℃; Enzymatic reaction;87%
bis(4-methoxyphenyl)amine
101-70-2

bis(4-methoxyphenyl)amine

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

(3R,5S,7R,8R,9S,10S,13R,14S,17R)-17-((R)-4-(bis(4-methoxyphenyl)amino)butan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol

(3R,5S,7R,8R,9S,10S,13R,14S,17R)-17-((R)-4-(bis(4-methoxyphenyl)amino)butan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol

Conditions
ConditionsYield
With 9-(2-chlorophenyl)acridine; di-tert-butyl peroxide; copper(II) hexafluoroacetylacetonate In ethyl acetate at 35℃; for 24h; Inert atmosphere; Irradiation;99%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

7-Ketolithocholic acid
4651-67-6

7-Ketolithocholic acid

Conditions
ConditionsYield
With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride In dichloromethane at -30℃; for 1.5h; Temperature; Swern Oxidation;98.6%
With sodium bromate; sulfuric acid; sodium bromide In dichloromethane at 20 - 30℃; for 6h;96.1%
With N-Bromosuccinimide In water; acetone at 20℃; for 2h; Darkness;94%
formic acid
64-18-6

formic acid

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

3α,7α-diformyloxy-5β-cholan-24-oic acid
6159-50-8, 6058-15-7

3α,7α-diformyloxy-5β-cholan-24-oic acid

Conditions
ConditionsYield
With perchloric acid In tetrahydrofuran at 50℃; for 15h;98%
With perchloric acid In tetrahydrofuran; water at 54℃; Inert atmosphere;96%
at 55℃; for 20h;95%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

2,2,2,-trichloroethoxycarbonyl azide

2,2,2,-trichloroethoxycarbonyl azide

2,2,2-trichloroethyl ((3R)-3-((3R,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)butyl)carbamate

2,2,2-trichloroethyl ((3R)-3-((3R,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)butyl)carbamate

Conditions
ConditionsYield
With dmap; copper diacetate In acetonitrile at 80℃; for 0.166667h; Schlenk technique; Sealed tube;98%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

ethylene diamine mono-p-toluenesulfonic acid salt
14034-59-4

ethylene diamine mono-p-toluenesulfonic acid salt

23-(4,5-dihydroimidazol-2-yl)-24-nor-5β-cholan-3α,7α-diol

23-(4,5-dihydroimidazol-2-yl)-24-nor-5β-cholan-3α,7α-diol

Conditions
ConditionsYield
at 220 - 225℃; for 0.75h;97%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

[(R)-4-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-acetic acid methyl ester
69320-16-7

[(R)-4-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-acetic acid methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide97%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

3,7-diketocholanic acid
859-97-2

3,7-diketocholanic acid

Conditions
ConditionsYield
With sodium bromate; ammonium cerium (IV) nitrate In water; acetonitrile at 80℃; Green chemistry;96%
With potassium bromate; phosphoric acid; potassium bromide In tetrahydrofuran; water; acetonitrile at 20℃; for 3h; Reagent/catalyst; Solvent; Temperature;90.6%
With aluminium(III) chloride hexahydrate; potassium peroxymonosulfate In water at 50℃; for 0.166667h; Microwave irradiation;83%
With chromium(VI) oxide; acetic acid
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

(2-(3)H(N))taurine

(2-(3)H(N))taurine

C26H44(3)HNO6S

C26H44(3)HNO6S

Conditions
ConditionsYield
With hydrogenchloride; tributyl-amine; chloroformic acid ethyl ester In 1,4-dioxane for 0.25h; Ambient temperature;95%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

(1,2-(14)C)taurine

(1,2-(14)C)taurine

C24(14)C2H45NO6S

C24(14)C2H45NO6S

Conditions
ConditionsYield
With hydrogenchloride; tributyl-amine; chloroformic acid ethyl ester In 1,4-dioxane for 0.25h; Ambient temperature;95%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

ferric chenodeoxycholate

ferric chenodeoxycholate

Conditions
ConditionsYield
With iron(III) chloride; sodium hydroxide In water at 35℃; pH=8;95%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

tri-Boc-spermine
114459-62-0

tri-Boc-spermine

N1-(3α,7α-dihydroxy-5β-cholan-24-carbonyl)-(N4,N9N12-tri-tert-butoxycarbonyl)-1,12-diamino-4,9-diazadodecane
287964-36-7

N1-(3α,7α-dihydroxy-5β-cholan-24-carbonyl)-(N4,N9N12-tri-tert-butoxycarbonyl)-1,12-diamino-4,9-diazadodecane

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 24h; Acylation;93%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

sodium taurochenodeoxycholate
6009-98-9

sodium taurochenodeoxycholate

Conditions
ConditionsYield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium hydroxide In water; acetonitrile; tert-butyl alcohol at 20 - 80℃;93%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl 3α,7α-dihydroxy-5β-cholan-24-oate
111992-94-0

benzyl 3α,7α-dihydroxy-5β-cholan-24-oate

Conditions
ConditionsYield
With caesium carbonate In acetonitrile Reflux;92%
With caesium carbonate In acetonitrile for 4h; Reflux;80%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 55℃;
With caesium carbonate In acetonitrile Reflux;
TMSCH2N2

TMSCH2N2

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate
14773-00-3

methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate

Conditions
ConditionsYield
In methanol; diethyl ether; toluene at 20℃; for 0.333333h;91%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

N1<(3α,5β,7α)3,7-dihydroxy-24-oxo-cholan-24-yl>N4methyl-piperazine
86678-67-3

N1<(3α,5β,7α)3,7-dihydroxy-24-oxo-cholan-24-yl>N4methyl-piperazine

Conditions
ConditionsYield
With tributyl-amine; chloroformic acid ethyl ester In 1,4-dioxane 10 deg C, 10 min then rt., 1 h;90%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

methylamine
74-89-5

methylamine

N methyl(3α,5β,7α)3,7-dihydroxy-cholan-24-amide
86678-62-8

N methyl(3α,5β,7α)3,7-dihydroxy-cholan-24-amide

Conditions
ConditionsYield
With tributyl-amine; chloroformic acid ethyl ester In 1,4-dioxane 10 deg C, 10 min then rt., 1 h;90%
With tributyl-amine; chloroformic acid ethyl ester Multistep reaction;
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

benzylamine
100-46-9

benzylamine

N benzyl (3α,5β,7α)3,7-dihydroxy-cholan-24-amide
86678-64-0

N benzyl (3α,5β,7α)3,7-dihydroxy-cholan-24-amide

Conditions
ConditionsYield
With tributyl-amine; chloroformic acid ethyl ester In 1,4-dioxane 10 deg C, 10 min then rt., 1 h;90%
With ammonium hydroxide; tributyl-amine; chloroformic acid ethyl ester Multistep reaction;

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