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128-13-2

Basic Information
CAS No.: 128-13-2
Name: Ursodeoxycholic acid
Article Data: 64
Molecular Structure:
Molecular Structure of 128-13-2 (Ursodeoxycholic acid)
Formula: C24H40O4
Molecular Weight: 392.579
Synonyms: (4R)-4-[(3R,5S,7S,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;Cholan-24-oic acid, 3,7-dihydroxy-, (3-.alpha.,5-.beta., 7-.beta.)-;Cholan-24-oic acid,3,7-dihydroxy-,(3R,5a,- 7a)-;UDCA;5.beta.-Chol-24-oic acid-3.alpha., 7.beta.-diol;Arsacol;Ursochol;Antigall;Urso (TN);Ursodiol;Antigall (TN);Actigall;Urso;Litursol;Deursil;Desocol;Ursodeoxycholic acid (JP14);Delursan;Ursodiol (USP);deoxy-;Urso Deoxy Cholic Acid;7beta-Hydroxylithocholic acid;Ursodeoxycholoc acid;
EINECS: 204-879-3
Density: 1.128 g/cm3
Melting Point: 203-204 °C(lit.)
Boiling Point: 547.1 °C at 760 mmHg
Flash Point: 298.8 °C
Solubility: practically insoluble in water
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36-26
PSA: 77.76000
LogP: 4.47790
Synthetic route
10538-55-3

3α,7β-dihydroxy-5β-cholan-24-oic acid methyl ester

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With methanol; sodium methylate at 25℃;99%
With water; sodium hydroxide at 97℃; for 2h; Large scale;49.1 kg
With water; sodium hydroxide at 120℃; for 12h;20.7 g
With water; sodium hydroxide at 120℃; for 12h; Time;29.4 g
4651-67-6

7-Ketolithocholic acid

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With glucose dehydrogenase; D-Glucose; NADPH; 7β-hydroxysteroid dehydrogenase In aq. phosphate buffer at 30℃; for 1h; pH=8; Concentration; pH-value; Enzymatic reaction;98%
With nicotinamide adenine dinucleotide phosphate; isopropyl alcohol In aq. phosphate buffer at 37℃; pH=7;93%
With potassium borohydride; potassium tert-butylate In isopropyl alcohol at 40℃; for 24h;92%
potassium ter.butylate

potassium ter.butylate

potassium 3,7-dioxo-5beta-cholanate

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; aluminum nickel In water98%

C24H36O4

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
Stage #1: C24H36O4 With potassium tert-butylate In tert-butyl alcohol for 0.5h;
Stage #2: With palladium 10% on activated carbon; hydrogen In tert-butyl alcohol at 80℃; under 3750.38 Torr; for 12h; Solvent; Reagent/catalyst; Temperature;
96%
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%

(3α,5β,7β)-7-hydroxy-3-[(4-nitrobenzoyl)oxy]-5-cholen-24-acid methyl ester

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 20℃; for 6h;94%

3α-hydroxy-7-keto-5β-chol-11-en-24-oic acid

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With potassium borohydride; potassium tert-butylate; hydrogen at 40℃; under 30003 Torr; for 24h;93%
With potassium borohydride; potassium tert-butylate; hydrogen In isopropyl alcohol at 40℃; under 30003 Torr; for 24h; Autoclave;93%
With potassium borohydride; potassium tert-butylate; hydrogen In isopropyl alcohol at 40℃; under 30003 Torr; for 24h;93%

(E)-7-hydroxy-3-oxo-4,6,22-choladienoic acid ethyl ester

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
Stage #1: (E)-7-hydroxy-3-oxo-4,6,22-choladienoic acid ethyl ester In 2-methyltetrahydrofuran at 90℃; under 30003 Torr; for 24h; Autoclave;
Stage #2: With sodium t-butanolate In 2-methyltetrahydrofuran; isopropyl alcohol at 90℃; under 30003 Torr; for 24h; Solvent; Reagent/catalyst; Temperature; Autoclave;
87%

C26H36O4

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
Stage #1: C26H36O4 With hydrogen In 2-methyltetrahydrofuran at 90℃; under 30003 Torr; for 24h; Autoclave;
Stage #2: With sodium t-butanolate In 2-methyltetrahydrofuran; isopropyl alcohol at 90℃; for 24h; Solvent; Reagent/catalyst; Temperature;
87%
474-25-9

chenodeoxycholic acid

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With NAD In methanol; aq. phosphate buffer at 25℃; for 24h; pH=8;86%
With 7β-hydroxysteroid dehydrogenase; Sepharose-CL6B; TEA; nicotinamide adenine dinucleotide In water at 20℃; for 120h;75%
Multi-step reaction with 2 steps
1: potassium phosphate, pyruvate, dithiothreitol, NAD / H2O / Ambient temperature; lactic dehydrogenase, 7α-hydroxysteroid dehydrogenase
2: potassium phosphate, glucose, dithiothreitol, NADP / H2O / glucose dehydrogenase, 7β-hydroxysteroid dehydrogenase
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    Ursodeoxycholic acid CAS No.:128-13-2 Name: Ursodeoxycholic acid Synonyms: 3,7-Dihydroxycholan-24-oic acid; 3alpha,7beta-Dihydroxy-6beta-cholan-24-oic acid; Ursodiol Molecular Structure Molecular Formula:

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Chemistry

Molecule structure of Ursodeoxycholic acid (CAS NO.128-13-2):

IUPAC Name: (4R)-4-[(3R,5S,7S,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 
Molecular Weight: 392.572 g/mol
Molecular Formula: C24H40O4 
Density: 1.128 g/cm3 
Melting Point: 203-204 °C(lit.)
Boiling Point: 547.1 °C at 760 mmHg 
Flash Point: 298.8 °C
Index of Refraction: 1.543
Molar Refractivity: 109.65 cm3
Molar Volume: 347.8 cm3
Surface Tension: 46 dyne/cm 
Enthalpy of Vaporization: 95.01 kJ/mol
Vapour Pressure: 2.98E-14 mmHg at 25 °C 
Solubility Ethanol: 50 mg/mL, clear
Water Solubility: practically insoluble
XLogP3-AA: 4.9
H-Bond Donor: 3
H-Bond Acceptor: 4
Rotatable Bond Count: 4
Exact Mass: 392.29266
MonoIsotopic Mass: 392.29266
Topological Polar Surface Area: 77.8
Heavy Atom Count: 28
Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4C@@]3(CC[C@H](C4)O)C)O)C
InChI: InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
InChIKey: RUDATBOHQWOJDD-UZVSRGJWSA-N
EINECS: 204-879-3
Product Categories: Bile Acids; Biochemistry; Steroids; Intermediates & Fine Chemicals; Pharmaceuticals; API's

Uses

 Ursodeoxycholic acid (CAS NO.128-13-2) can be used as an anticholelithogenic.

Production

 Ursodeoxycholic acid is found in large quantities in bear bile.

Toxicity Data With Reference

1.    

mmo-sat 40 mg/L

    MUREAV    Mutation Research. 158 (1985),45.
2.    

orl-rat TDLo:11,900 mg/kg (4-20D preg):TER

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 246 (1980),149.
3.    

orl-rat LD50:4600 mg/kg

    BCFAAI    Bollettino Chimico Farmaceutico. 126 (1987),282.
4.    

ipr-rat LD50:890 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),95.
5.    

ivn-rat LD50:310 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),95.
6.    

ivn-mus LD50:240 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),95.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26 
S24/25:Avoid contact with skin and eyes. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS: FZ2000000
F: 10
Poison by intraperitoneal and intravenous routes. Experimental teratogenic and reproductive effects. Mutation data reported. Stimulates the flow of bile to the duodenum (a cholagogic). When heated to decomposition it emits acrid smoke and irritating fumes.

Specification

 Ursodeoxycholic acid (CAS NO.128-13-2) is also named as 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3-alpha,7-beta-diol ; 3,7-Dihydroxycholan-24-oic acid ; 3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid ; 3-alpha,7-beta-Dihydroxycholanic acid ; 3-alpha,7-beta-Dioxycholanic acid ; 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid ; 4-10-00-01604 (Beilstein Handbook Reference) ; 7-beta-Hydroxylithocholic acid ; Actigall ; Arsacol ; BRN 3219888 ; CCRIS 5502 ; Cholit-ursan ; Delursan ; Destolit ; Deursil ; Litursol ; Lyeton ; NSC 657950 ; NSC 683769 ; Peptarom ; Solutrat ; UNII-724L30Y2QR ; UrSO ; Ursacol ; Urso 250 ; Urso DS ; Urso Forte ; Ursobilin ; Ursochol ; Ursocholic acid, deoxy- ; Ursodamor ; Ursodeoxycholate ; Ursodiol ; Ursofalk ; Ursolvan . Ursodeoxycholic acid (CAS NO.128-13-2) is white crystalline powder.

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