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474-25-9

Basic Information
CAS No.: 474-25-9
Name: Chenodeoxycholic acid
Article Data: 72
Molecular Structure:
Molecular Structure of 474-25-9 (Chenodeoxycholic acid)
Formula: C24H40O4
Molecular Weight: 392.579
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;
EINECS: 207-481-8
Density: 1.129 g/cm3
Melting Point: 165-167 °C(lit.)
Boiling Point: 547.148 °C at 760 mmHg
Flash Point: 298.8 °C
Solubility: practically insoluble in water
Appearance: Off-white solid
Hazard Symbols: HarmfulXn
Risk Codes: 63
Safety: 22-24/25-45-36/37
PSA: 77.76000
LogP: 4.47790
Synthetic route

3α,7α-Dihydroxy-chol-11-ensaeure

474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
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
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%
4651-67-6

7-Ketolithocholic acid

A

474-25-9

chenodeoxycholic acid

B

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%
4651-67-6

7-Ketolithocholic acid

474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
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
ConditionsYield
With water; sodium hydroxide In methanol for 6h; Reflux;90.9%
2458-08-4

3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic 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;
2616-71-9

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

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
28535-81-1

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

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

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

474-25-9

chenodeoxycholic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 80℃; for 4h;30%
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Chemistry

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

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.

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.

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: HarmfulXn
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

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 .