chenodeoxycholic acid
Conditions | Yield |
---|---|
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
chenodeoxycholic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
chenodeoxycholic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol for 6h; Reflux; | 90.9% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
chenodeoxycholic acid
Conditions | Yield |
---|---|
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 |
chenodeoxycholic acid
Conditions | Yield |
---|---|
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% |
chenodeoxycholic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol at 80℃; for 4h; | 30% |
chenodeoxycholic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol at 75℃; for 6h; | 28% |
chenodeoxycholic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol at 75℃; for 5h; | 28% |
chenodeoxycholic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol at 60℃; for 8h; | 26% |
Conditions | Yield |
---|---|
With ethanol; platinum Hydrogenation; | |
With acetic acid; platinum Hydrogenation; | |
With sodium tetrahydroborate; water; sodium hydroxide |
Conditions | Yield |
---|---|
With aluminum isopropoxide; isopropyl alcohol |
7-Ketolithocholic acid
sodium ethanolate
A
chenodeoxycholic acid
B
ursodeoxycholic acid
Conditions | Yield |
---|---|
at 200℃; |
methyl 3α-hydroxy-7α-acetoxy-12-oxocholanate
chenodeoxycholic acid
Conditions | Yield |
---|---|
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
aluminum isopropoxide
isopropyl alcohol
A
chenodeoxycholic acid
B
ursodeoxycholic acid
3α,7α-dihydroxy-12-oxocholanic acid tosylhydrazone
chenodeoxycholic acid
Conditions | Yield |
---|---|
With sodium tetrahydroborate In acetic acid for 3h; Ambient temperature; |
7-hydroxy-3-(sulfooxy)-(3α,5β,7α)-cholan-24-oic acid
chenodeoxycholic acid
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; acetone at 37℃; for 18h; Product distribution; solvolyse methods, var. of temp., solvent, reagent and time; |
chenodeoxycholic acid 7-sulfate
chenodeoxycholic acid
Conditions | Yield |
---|---|
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; |
B
chenodeoxycholic acid
Conditions | Yield |
---|---|
With acetate buffer; glycyrrhizinic acid hydrolase at 45℃; hydrolysis; other enzyme (β-glucuronidase); |
(25RS)-3α,7α-dihydroxy-5β-cholestan-26-oic acid
chenodeoxycholic acid
Conditions | Yield |
---|---|
rat liver homogenate, NAD, pH=8.5; |
chenodeoxycholic acid
Conditions | Yield |
---|---|
rat liver homogenate, NAD, pH=8.5; |
chenodeoxycholic acid
Conditions | Yield |
---|---|
rat liver homogenate, NAD, pH=8.5; |
A
chenodeoxycholic acid
Conditions | Yield |
---|---|
In water; ethylene glycol at 25℃; Equilibrium constant; decomplexation; |
A
chenodeoxycholic acid
Conditions | Yield |
---|---|
In water; ethylene glycol at 25℃; Equilibrium constant; decomplexation; |
A
chenodeoxycholic acid
Conditions | Yield |
---|---|
In water; ethylene glycol at 25℃; Equilibrium constant; decomplexation; |
chenodeoxycholic acid
Conditions | Yield |
---|---|
With potassium hydroxide; ethylene glycol weiteres Reagens: N2H4; | |
With potassium hydroxide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol weiteres Reagens: N2H4; |
Conditions | Yield |
---|---|
With thionyl chloride | 100% |
With toluene-4-sulfonic acid at 20℃; for 1h; | 100% |
With toluene-4-sulfonic acid for 2h; Reflux; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; D-glucose; Pseudomonas paucimobilis; yeast extracxt; peptone In water at 28℃; for 24h; | 100% |
chenodeoxycholic acid
diazomethyl-trimethyl-silane
chenodeoxycholic acid methyl ester
Conditions | Yield |
---|---|
In methanol; hexane; toluene at 20℃; | 100% |
N-Methyltaurine
chenodeoxycholic acid
3α,7α-dihydroxy-5β-cholan-24-oyl-N-methyltaurine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
100% |
chenodeoxycholic acid
acetic anhydride
3α,7α-diacetoxy-24-phenyl-5β-cholan-24-oic acid
Conditions | Yield |
---|---|
With pyridine at 20℃; for 24h; | 99% |
With pyridine at 20℃; for 3h; | 97% |
With pyridine at 20℃; for 15h; | 95% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With 9-(2-chlorophenyl)acridine; di-tert-butyl peroxide; copper(II) hexafluoroacetylacetonate In ethyl acetate at 35℃; for 24h; Inert atmosphere; Irradiation; | 99% |
Conditions | Yield |
---|---|
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
chenodeoxycholic acid
3α,7α-diformyloxy-5β-cholan-24-oic acid
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With dmap; copper diacetate In acetonitrile at 80℃; for 0.166667h; Schlenk technique; Sealed tube; | 98% |
chenodeoxycholic acid
ethylene diamine mono-p-toluenesulfonic acid salt
Conditions | Yield |
---|---|
at 220 - 225℃; for 0.75h; | 97% |
chenodeoxycholic acid
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
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide | 97% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With hydrogenchloride; tributyl-amine; chloroformic acid ethyl ester In 1,4-dioxane for 0.25h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With hydrogenchloride; tributyl-amine; chloroformic acid ethyl ester In 1,4-dioxane for 0.25h; Ambient temperature; | 95% |
chenodeoxycholic acid
Conditions | Yield |
---|---|
With iron(III) chloride; sodium hydroxide In water at 35℃; pH=8; | 95% |
chenodeoxycholic acid
tri-Boc-spermine
N1-(3α,7α-dihydroxy-5β-cholan-24-carbonyl)-(N4,N9N12-tri-tert-butoxycarbonyl)-1,12-diamino-4,9-diazadodecane
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 24h; Acylation; | 93% |
Conditions | Yield |
---|---|
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium hydroxide In water; acetonitrile; tert-butyl alcohol at 20 - 80℃; | 93% |
chenodeoxycholic acid
benzyl bromide
benzyl 3α,7α-dihydroxy-5β-cholan-24-oate
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
In methanol; diethyl ether; toluene at 20℃; for 0.333333h; | 91% |
1-methyl-piperazine
chenodeoxycholic acid
N1<(3α,5β,7α)3,7-dihydroxy-24-oxo-cholan-24-yl>N4methyl-piperazine
Conditions | Yield |
---|---|
With tributyl-amine; chloroformic acid ethyl ester In 1,4-dioxane 10 deg C, 10 min then rt., 1 h; | 90% |
chenodeoxycholic acid
methylamine
N methyl(3α,5β,7α)3,7-dihydroxy-cholan-24-amide
Conditions | Yield |
---|---|
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
benzylamine
N benzyl (3α,5β,7α)3,7-dihydroxy-cholan-24-amide
Conditions | Yield |
---|---|
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; |
Structure of Chenodeoxycholic acid (CAS NO.474-25-9):
IUPAC Name: (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,
3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Empirical Formula: C24H40O4
Molecular Weight: 392.572
EINECS: 207-481-8
Index of Refraction: 1.543
Molar Refractivity: 109.65 cm3
Molar Volume: 347.8 cm3
Polarizability: 43.46×10-24cm3
Surface Tension: 46 dyne/cm
Density: 1.128 g/cm3
Flash Point: 298.8 °C
Enthalpy of Vaporization: 95.01 kJ/mol
Melting Point: 165-167 °C(lit.)
Boiling Point: 547.1 °C at 760 mmHg
Vapour Pressure: 2.98E-14 mmHg at 25°C
Water Solubility: PRACTICALLY INSOLUBLE
Physical Appearance: Off-White Solid
Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Intracellular receptor
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.
1. | mmo-sat 20 mg/L | MUREAV Mutation Research. 158 (1985),45. | ||
2. | sln-smc 100 mg/L | CRNGDP Carcinogenesis. 5 (1984),447. | ||
3. | orl-wmn TDLo:24 g/kg/5Y-C:CAR | CLONEA Clinics in Oncology. 7 (1981),245. | ||
4. | orl-rat LD50:4000 mg/kg | IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. 13 (1982),1128. | ||
5. | ipr-rat LD50:105 mg/kg | OYYAA2 Oyo Yakuri. Pharmacometrics. 15 (1978),915. | ||
6. | ivn-rat LD50:106 mg/kg | OYYAA2 Oyo Yakuri. Pharmacometrics. 15 (1978),915. | ||
7. | orl-mus LD50:3000 mg/kg | IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. 13 (1982),1128. | ||
8. | ipr-mus LD50:86 mg/kg | OYYAA2 Oyo Yakuri. Pharmacometrics. 15 (1978),915. | ||
9. | ivn-mus LD50:100 mg/kg | ARZNAD Arzneimittel-Forschung. Drug Research. 20 (1970),323. |
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Questionable human carcinogen producing liver tumors. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes: Xn
Risk Statements: 63
R63:Possible risk of harm to the unborn child.
Safety Statements: 22-24/25-45-36/37
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37:Wear suitable protective clothing and gloves.
WGK Germany: 2
RTECS: FZ1980000
Chenodeoxycholic acid , its cas register number is 474-25-9. It also can be called 3-alpha,7-alpha-Dihydroxy-5-beta-cholan-24-oic acid ; 3-alpha,7-alpha-Dihydroxycholanic acid ; 3-alpha,7-alpha-Dihydroxycholansaeure ; 3alpha,7alpha-Dihydroxy-5beta-cholan-24-oic acid ; 7-alpha-Hydroxylithocholic acid ; Acide chenodeoxycholique ; Acido chenodeoxicholico ; Anthropodeoxycholic acid ; Anthropododesoxycholic acid ; Chenic acid ; Chenix ;
Chenodesoxycholsaeure ; Chenodiol ; Gallodesoxycholic acid .
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