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128-13-2

Basic Information
CAS No.: 128-13-2
Name: Ursodeoxycholic acid
Molecular Structure:
Molecular Structure of 128-13-2 (Ursodeoxycholic acid)
Formula: C24H40O4
Molecular Weight: 392.58 .
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
Transport Information:
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
View Scheme
434-13-9

Lithocholic acid

A

128-13-2

ursodeoxycholic acid

B

77060-26-5

3-keto-7β-hydroxy-5β-cholan-24-oic acid

Conditions
ConditionsYield
With Gibberella zeae VKM F-2600 extract In methanol; aq. phosphate buffer at 29℃; for 122h; pH=7; Microbiological reaction;A 83%
B n/a
81873-91-8

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

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With hydrazine hydrate; potassium hydroxide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 110 - 135℃; Wolf-Kishner reduction;82%

methyl 3α-acetoxy-7-keto-5β-chol-11-enoate

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With potassium borohydride; potassium tert-butylate; hydrogen at 40℃; under 30003 Torr; for 24h;80%
Multi-step reaction with 2 steps
1: sodium hydroxide; water / methanol; tetrahydrofuran / 4 h / Reflux; Inert atmosphere
2: potassium tert-butylate; potassium borohydride; hydrogen / isopropyl alcohol / 24 h / 40 °C / 30003 Torr / Autoclave
View Scheme

7-ketochenodeoxycholic acid sodium salt

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; 7β-hydroxysteroid dehydrogenase; 2-hydroxyethanethiol; ethylenediaminetetraacetic acid In phosphate buffer at 20℃; for 48h; pH=7;75%

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

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
Stage #1: ethyl 3α-benzoyloxy-7β-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;
71%
7753-72-2

methyl 3,7-dioxocholan-24-oate

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With ammonia; lithium In tetrahydrofuran; methanol at -50℃; for 1h;68%
10452-65-0

methyl 3α-acetoxy-7-oxo-5β-cholan-24-oate

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With sodium In butan-1-ol at 20 - 60℃; for 2.25h; Inert atmosphere;62%
474-25-9

chenodeoxycholic acid

A

128-13-2

ursodeoxycholic acid

B

4651-67-6

7-Ketolithocholic acid

Conditions
ConditionsYield
With air; Xanthomonas maltophilia CBS 827.97 In sodium hydroxide at 30℃; for 4h; pH=8; epimerisation;A 27%
B 23%
With Xanthomonas maltophilia In water at 30℃; for 24h; pH=8; anaerobic;A 27%
B 23%
859-97-2

3,7-diketocholanic acid

A

474-25-9

chenodeoxycholic acid

B

128-13-2

ursodeoxycholic acid

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

7-Ketolithocholic acid

141-52-6

sodium ethanolate

A

474-25-9

chenodeoxycholic acid

B

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
at 200℃;
859-97-2

3,7-diketocholanic acid

555-31-7

aluminum isopropoxide

67-63-0

isopropyl alcohol

A

474-25-9

chenodeoxycholic acid

B

128-13-2

ursodeoxycholic acid

81857-23-0

methyl 3-O-acetyl-7-O-mesylchenodeoxycholate

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With potassium superoxide; 18-crown-6 ether In dimethyl sulfoxide for 3h; Yield given;
6A,6D-bis(2-naphthylsulfonyl)-γ-cyclodextrin ursodeoxycholic acid 1:1 complex

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

A

128-13-2

ursodeoxycholic 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 ursodeoxycholic acid 1:1 complex

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

A

128-13-2

ursodeoxycholic 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;
7647-01-0

hydrogenchloride

4651-67-6

7-Ketolithocholic acid

64-19-7

acetic acid

platinum

platinum

A

474-25-9

chenodeoxycholic acid

B

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
Hydrogenation;
92411-07-9

[3H] Sodium glycoursodeoxycholate

A

128-13-2

ursodeoxycholic acid

B

56-40-6

glycine

Conditions
ConditionsYield
With chloylglycine hydrolase In phosphate buffer at 84℃; for 0.0833333h;
16564-43-5

glycochenodeoxycholic acid sodium salt

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent Chromat. / chloylglycine hydrolase; β-mercaptoethanol; EDTA / aq. phosphate buffer / 3 h / 20 °C / pH 8
2: 75 percent / Sepharose-CL6B; 7β-hydroxysteroid dehydrogenase; TEA / NAD(+) / H2O / 120 h / 20 °C
View Scheme
6009-98-9

sodium taurochenodeoxycholate

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent Chromat. / chloylglycine hydrolase; β-mercaptoethanol; EDTA / aq. phosphate buffer / 0.33 h / 20 °C / pH 8
2: 75 percent / Sepharose-CL6B; 7β-hydroxysteroid dehydrogenase; TEA / NAD(+) / H2O / 120 h / 20 °C
View Scheme
10538-64-4

methyl 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oate

128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 52 percent / acetic acid / 12 h / Ambient temperature
2: 57 percent / NaBH4 / acetic acid / 3 h / Ambient temperature
3: pyridine / benzene
4: pyridine / Ambient temperature
5: KO2/18-crown-6 ether / dimethylsulfoxide / 3 h
View Scheme
107-68-6

N-Methyltaurine

128-13-2

ursodeoxycholic acid

3α,7β-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%
67-56-1

methanol

128-13-2

ursodeoxycholic acid

10538-55-3

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 2.5h; Reflux;98%
With sulfuric acid at 50℃; for 3h;97%
With toluene-4-sulfonic acid at 65℃; for 2.5h;97%
128-13-2

ursodeoxycholic acid

108-24-7

acetic anhydride

6533-77-3

(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-diacetoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

Conditions
ConditionsYield
In pyridine at 20℃; for 12h;98%
With dmap In dichloromethane at 20℃; for 1h; Inert atmosphere;95%
With pyridine at 20℃; Inert atmosphere;92%
128-13-2

ursodeoxycholic acid

70-70-2

4-hydroxypropiophenone

C33H48O5

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 10 - 20℃; for 2h; Temperature; Concentration;97.3%
64-18-6

formic acid

128-13-2

ursodeoxycholic acid

6058-15-7, 6159-50-8

(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-bis(formyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

Conditions
ConditionsYield
at 55℃; for 20h;96%
With perchloric acid96%
1) 65 deg C, 4 h, 2) 25 deg C, 20 h;95%
128-13-2

ursodeoxycholic acid

ferric ursodeoxycholate

Conditions
ConditionsYield
With iron(III) chloride; sodium hydroxide In water at 35℃; pH=8;95%
128-13-2

ursodeoxycholic acid

35807-85-3

tauroursodeoxycholic acid sodium salt

Conditions
ConditionsYield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium hydroxide In water; acetonitrile; tert-butyl alcohol at 20 - 80℃;95%
128-13-2

ursodeoxycholic acid

100-39-0

benzyl bromide

111992-93-9

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

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 3h;95%
With potassium carbonate In acetonitrile at 80℃; for 3h;95%
Stage #1: ursodeoxycholic acid With potassium hydrogencarbonate In N,N-dimethyl-formamide for 0.333333h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide for 48h;
95%
With potassium carbonate In acetonitrile at 80℃; for 3h;95%
With caesium carbonate In acetonitrile for 4h; Reflux;82%
128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;94%
With lithium aluminium tetrahydride
Multi-step reaction with 2 steps
1: thionyl chloride / 3.5 h / 20 °C / Reflux
2: sodium tetrahydroborate; ethanol / 20 °C
View Scheme
64-17-5

ethanol

128-13-2

ursodeoxycholic acid

69519-36-4

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 24h; Ambient temperature;93%
128-13-2

ursodeoxycholic acid

6000-43-7

2-aminoethanoic acid hydrochloride

115488-03-4

glycine ursodeoxycholic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In acetone for 12h; Solvent; Time; Reflux;93%
128-13-2

ursodeoxycholic acid

75-36-5

acetyl chloride

10538-55-3

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

Conditions
ConditionsYield
In methanol at 0 - 20℃; for 6h;92%
128-13-2

ursodeoxycholic acid

A

88426-32-8

3,7-bis(sulfooxy)ursodeoxycholic acid

B

59132-32-0, 64520-49-6, 68780-68-7, 68833-02-3, 124815-69-6, 68780-73-4

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

C

74723-14-1

7-(sulfooxy)ursodeoxycholic acid

Conditions
ConditionsYield
With pyridine; sulfur trioxide pyridine complex at 0 - 20℃; for 0.166667h; other temperatures, other times, other reagent ratio;A 91.9%
B 4.1%
C 2.6%
With pyridine; sulfur trioxide pyridine complex at -5℃; for 0.166667h; Product distribution; other temperatures, other reaction times, other reagent ratio;A 25%
B 31.2%
C 25%
With pyridine; sulfur trioxide pyridine complex at -5℃; for 0.166667h; other temperatures, other times, other reagent ratio;A 25%
B 31.2%
C 25%
With pyridine; sulfur trioxide pyridine complex at -5℃; for 0.166667h; other temperatures, other times, other reagent ratio;A 25%
B 31.2%
C 25%
63147-26-2

trimethyl-sulfo-ammonium betaine

128-13-2

ursodeoxycholic acid

ursodeoxycholic acid di-trimethylammonium 3,7-disulfate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40 - 90℃;91.6%
Conditions
ConditionsYield
Stage #1: ursodeoxycholic acid; glycine With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium hydroxide In water; acetonitrile; tert-butyl alcohol at 20 - 80℃;
Stage #2: With hydrogenchloride In water pH=2;
91%
109-01-3

1-methyl-piperazine

128-13-2

ursodeoxycholic acid

86678-72-0

N1<(3α,5β,7β)3,7-dihydroxy-24-oxo-cholan-24-yl>N4 methyl-piperazine

Conditions
ConditionsYield
With tributyl-amine; chloroformic acid ethyl ester In 1,4-dioxane 10 deg C, 10 min then rt., 1 h;90%
128-13-2

ursodeoxycholic acid

77060-26-5

3-keto-7β-hydroxy-5β-cholan-24-oic acid

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; D-glucose; Pseudomonas paucimobilis; yeast extracxt; peptone In water at 28℃; for 24h;90%
Multi-step reaction with 4 steps
1: triethylamine; DMAP / ethyl acetate / 10 h / Heating
2: 5percent NaOH / methanol / 1 h
3: Jones' reagent / acetone / 0.08 h
4: 95 percent / 20percent NaOH / 1 h / Heating
View Scheme
128-13-2

ursodeoxycholic acid

147-94-4

arabinosyl cytosine

(4R)-N-(1-((3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-furan-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamide

Conditions
ConditionsYield
Stage #1: ursodeoxycholic acid With triethylamine; isobutyl chloroformate In N,N-dimethyl-formamide at -15℃; for 0.25h; Inert atmosphere;
Stage #2: arabinosyl cytosine With triethylamine In N,N-dimethyl-formamide at -15 - 20℃; for 0.5h; Inert atmosphere;
87%
Stage #1: ursodeoxycholic acid With triethylamine; isobutyl chloroformate In N,N-dimethyl-formamide at -15℃; for 0.0833333h;
Stage #2: arabinosyl cytosine With triethylamine In N,N-dimethyl-formamide at -15 - 20℃; for 2.5h;
123-75-1

pyrrolidine

128-13-2

ursodeoxycholic acid

(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-(pyrrolidin-1-yl)pentan-1-one

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 16h;87%
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 16h;87%
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    Ursodeoxycholic acid

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    Ursodeoxycholic acid Quick Details CAS No.: 128-13-2 Other Names: Ursodeoxycholic Acid MF: C24H40O4 EINECS No.: 204-879-3 Place of Origin:

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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.