- Chenodeoxycholic acid
- Chenodeoxycholic acid sodium salt
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Cas Database |
| Name |
Chenodeoxycholic acid |
EINECS | 207-481-8 |
| CAS No. | 474-25-9 | Density | 1.129 g/cm3 |
| PSA | 77.76000 | LogP | 4.47790 |
| Solubility | practically insoluble in water | Melting Point |
165-167 °C(lit.) |
| Formula | C24H40O4 | Boiling Point | 547.148 °C at 760 mmHg |
| Molecular Weight | 392.579 | Flash Point | 298.8 °C |
| Transport Information | N/A | Appearance | Off-white solid |
| Safety | 22-24/25-45-36/37 | Risk Codes | 63 |
| Molecular Structure |
|
Hazard Symbols |
 Xn
|
| Synonyms |
Anthropodeoxycholic acid;Cholan-24-oic acid,3,7-dihydroxy-,(3R,5a,- 7R)-;Chenodiol [USAN];7-alpha-Hydroxylithocholic acid;Anthropododesoxycholic acid;Acido chenodeoxicholico [INN-Spanish];Chenodesoxycholic acid;Cholan-24-oic acid, 3,7-dihydroxy-, (3-.alpha., 5-.beta., 7-.alpha.)-;Acidum chenodeoxycholicum [INN-Latin];Anthropodesoxycholic acid;Chenodeoxycholic acid (JAN);(4R)-4-[(3R,5S,7R,8R,9S,10R,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]pentanoate;Chendol;3-alpha,7-alpha-Dihydroxy-5-beta-cholan-24-oic acid;Prestwick_553;3-alpha,7-alpha-Dihydroxycholanic acid;Cholan-24-oic acid, 3,7-dihydroxy-, (3-alpha,5-beta,7-alpha)- (9CI);Chenodiol;Chenodesoxycholsaeure [German];5-beta-Cholan-24-oic acid, 3-alpha,7-alpha-dihydroxy-;(4R)-4-[(3R,5S,7R,8S,9S,10R,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;Chenodeoxycholate; |
Article Data | 72 |
Chenodeoxycholic acid Synthetic route
- 474-25-9
chenodeoxycholic acid
| Conditions | Yield |
|---|---|
| With palladium on activated charcoal; hydrogen In methanol at 70℃; under 30003 Torr; for 12h; | 99% |
- 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
- 474-25-9
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% |
- 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
- 474-25-9
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 |
- 28535-81-1
methyl 3α,7α-diacetoxy-12-one-5β-cholest-24-carboxylate
- 474-25-9
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 |
- 474-25-9
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% |
- 474-25-9
chenodeoxycholic acid
| Conditions | Yield |
|---|---|
| With water; sodium hydroxide In methanol at 80℃; for 4h; | 30% |
Chenodeoxycholic acid Chemical Properties
Structure of Chenodeoxycholic acid (CAS NO.474-25-9):
.gif)
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
Chenodeoxycholic acid 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 facilitates its excretion.
Chenodeoxycholic acid Toxicity Data With Reference
| 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. |
Chenodeoxycholic acid Safety Profile
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 Specification
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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