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Cas No: 128-13-2
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128-13-2 Bulk Powder UDCA Ursodeoxycholic Acid
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128-13-2 Usage

Determination of the content ursodeoxycholic acid and chenodeoxy

(1) Tested sample: The dried bile of brown bear Ursus arctos Linnaeus or black bear Selenarctos thibetanus G.Cuvier.
(2) Chromatographic conditions: High silica gel thin layer plate (Yantai); isooctane-isopropyl ether-acetic acid-butanol-water (6: 3: 3: 1.8: 0.6) as developing solvent; 5% sulfuric acid-ethanol solution of saturated ammonium bisulfate as coloring agents; Spray for coloring, heat at 110 °C for 10min, check the spot position in natural light under 365nm UV lamp.
(3) The preparation of the reference solution: Precisely weigh reference samples of ursodeoxycholic acid, chenodeoxycholic acid, bile acid. Dissolve it in methanol to obtain a reference solution of 1mg per milliliter.
(4) Preparation of sample solution: Precisely weigh 8mg bear bile, add 1.5 mL 30% sodium hydroxide solution, hydrolyze for 10 h in a boiling water bath. Adjust pH to 1~2 with concentrated hydrochloric, extract with ethyl acetate (10ml × 2 times, 5ml × 2 times), combine the extract and concentrate into 2 mL in volume flask, as the sample solution.
(5) Determination: Pipette 1μl sample solution and reference solution 1μl and 2μl, respectively. Crossly dot the samples in the same plate, According to the above-mentioned TLC conditions, develop, take out, dry, and color. Apply reflection zigzag scanning method according TLCS scanning protocol, use excitation wavelength of ursodeoxycholic acid λ ex = 380nm, emission wavelength λ em = 450nm; For chenodeoxycholic acid and bile acids, use λem = 470nm, λex = 550nm. Measure the absorption integral value of sample and reference sample, calculate and obtain the final result.
(6) Chromatograms
The TLC diagram of bear bile using TLCS method
Figure 2 The TLC diagram of bear bile using TLCS method.
Notes: 1 natural bear bile; 2 bile powder; 3 Bears gallstones; 4 Reference sample;
a. ursodeoxycholic acid; b.goose deoxycholate acid.
(7) measurement results
 The content of ursodeoxycholic acid and chenodeoxycholic acid in bear bile
Figure 3 The content of ursodeoxycholic acid and chenodeoxycholic acid in bear bile

Brand name

Actigall (Watson); Urso (Axcan Scandipharm).

Purification Methods

Recrystallise ursodiol from wet Et2O, EtOH or EtOH/MeOH. [Iwasaki Hoppe Seyler's Z Physiol Chem 244 181, 183 1936, Beilstein 10 III 1635.]

Chemical Properties

WHITE CRYSTALLINE POWDER

Uses

Used as an anticholelithogenic. Epimer with Chenodiol with respect to the hydroxyl group at C7.

Uses

anticholelithogenic; LD50(rat) 890 mg/kg ip

Production method

Method 1: Use chenodeoxycholic acid as raw materials
Preparation of 3α, 7α-diacetyl cholic acid methyl ester; Take 36ml of anhydrous methanol, and pass through 1g dried hydrogen chloride gas, add bile acid 12g, stir, heat and reflux for 20-30min. After standing for several hours at room temperature when crystals are separated out, freeze, filter, wash with ether, and dry to obtain methyl cholate. Take 2g methyl cholate, add 9.6 mL of benzene, 2.4mL pyridine, 2.4 mL of acetic anhydride, shake for 10-15min, stand for 20h at room temperature, then pour the reaction mixture into 100ml of water, remove the benzene layer, repeatedly wash with distilled water before recycling the solvents. Wash the solid residue with petroleum ether once, and re-crystallize with methanol-aqueous solution to obtain 3α, 7α-diacetyl bile acid methyl ester.
Bile acid methyl → → 3α, 7α-diacetyl bile acid methyl ester
Preparation of Chenodeoxycholic acid: Take the 1.5 g diacetyl bile acid methyl ester, add 24 mL acetic acid, add potassium chromate solution (Take 0.76g potassium chromate to dissolve it in 1.8ml take in water), heated to 40 °C, perform reaction for 8h, add water 120ml, shaking for some moment, placed 12h, filter, wash with distilled water till neutralization, dry to give 3α, 7α-diacetoxy-12-keto bile acid methyl ester, referred briefly as the 12-ketone. Take 12-15 g 12-ketone, add 150 mL 2-glycol ether, 15 mL 80% hydrazine hydrate solution, and 15 g potassium hydroxide. Heat to 30 °C and reflux for 15h, heat to 195-200 °C, refluxed for 2.5h, heat to 217 °C for some moment of reaction cool to 190 °C, add 0.7ml hydrazine hydrate solution, heat from within 215 °C to 220 °C within 3h, cool, add 600mL distilled water, adjust to pH 3 with 10% sulfuric acid, separate out the crystals, filter, wash with water until neutralization. Add ethyl acetate, dump the aqueous layer, use water to wash the organic layer was washed for 1-2 times, vacuum distillation and obtain 3α, 7α-dihydroxy cholanic acid, namely Chenodeoxycholic acid.
3α, 7α-diacetyl methyl cholate → 3α, 7α-diacetoxy-12-Keto ursodeoxycholic acid methyl ester → 3α, 7α-dihydroxy ursodeoxycholic acid (Chenodeoxycholic acid)
Preparation of refined ursodeoxycholic acid; Taken 2 g chenodeoxycholic acid, add 100ml of acetic acid and 20g potassium acetate, shake to dissolve. Add potassium chromate 1.5g (dissolved in 10 mL of water), at room temperature overnight, add water 200ml, separate out the crystals, filter, wash, and dry to obtain 3α-hydroxy-7-keto-ursodeoxycholic acid. Take 4g 3α-hydroxy-7-keto-ursodeoxycholic acid, add 100 mL n-butanol, heat to about 115 °C, gradually add 8 g metal sodium after which, white slurry gradually comes out, keep reaction for 30min, add 120ml water, stir and heat to transparently dissolve. Evaporate the organic layer under reduced pressure; add 500 mL water to the residue, dissolve, and filter. Adjust the pH the filtrate to pH 3 with 10% sulfuric acid which will yield white precipitate, filter, wash till neutralization with water, dry, wash with ethyl acetate, crystallize with diluted ethanol and obtain 3α, 7β-dihydroxycholanic acid, that’s refined ursodeoxycholic acid.
Chenodeoxycholic acid [potassium chromate] → 3α-hydroxy-7-keto acid [sodium metal, 115 °C] → 3α, 7β-Keto ursodeoxycholic acid methyl ester (Ursodeoxycholic acid)
Method 2: Use pig bile or bile salts as raw material; Use thin layer chromatography to isolate ursodeoxycholic acid from pigs bile or bile salt. Pig bile salt contains free and bound type of UDCA whose content is about 30%; pig bile contains bound UDCA whose content is about 0.6%.

Precautions

(1) For elderly patients, apply with caution.
(2) Long-term use can increase the number of peripheral platelet.
(3) If biliary colic occurs recurrently during the treatment of cholesterol gallstones and the symptoms are not alleviated or even become worse or clear stones calcification happen, stop the treatment and apply surgery.
(4) This product cannot used to dissolve bile pigment stones, mixed stones and stones cannot be penetrated by X-ray.
(5) Check liver function regularly during the treatment.

Chemical Properties

White powder; odorless, bitter taste. M.p.: 200-204 °C. Highly soluble in ethanol and glacial acetic acid, soluble in sodium hydroxide solution but insoluble in chloroform. UDCA is the isomer of CDCA, which has stronger stone-dissolving effect than CDCA and cause no diarrhea and liver toxicity. UDCA can reduce the absorption of cholesterol, and can reduce the synthesis of cholesterol and the level of cholesterol in bile. In addition, UDCA can also reduce the concanavalin A-binding fragment. The substance can also promote the formation of bile crystallize, thereby inhibiting the formation of stones. Applying the UDCA and CDCA in combination can enhance their effect when used alone while also reducing side effects. The combination of these two drugs is mainly for the treatment of cholesterol gallstones. UDCA has a fastest rate of dissolving stone when patient’s bile and stone have similar density or the CT value of gallstone is lower than 75 units. Cholelithiasis patients will have increased peripheral platelet number after using this product.

Definition

ChEBI: A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.

Uses

1. Gallstone-dissolving drugs. Mainly used for the treatment of inoperable cholesterol gallstones, it will have a cure rate especially in the case when gallbladder is basically normal, stones have a 15mm or lower diameters, X-ray penetrable, non-calcified and high-floating cholesterol stones. It also has some therapeutic effect against toxic hepatitis, cholecystitis, primary sclerosing cholangitis, and primary cholestatic cirrhosis. It can also improve the efficacy of α-interferon on treatment of chronic hepatitis C. It can also used to treat diarrhea, rare constipation, allergic reactions, itching, headache, dizziness, stomach pain, pancreatitis and bradycardia Patients of completely biliary obstruction or severe liver dysfunction and pregnant women should avoid using.
2. For the prevention and treatment of cholesterol gallstones.
3. Anionic detergents, for biochemical research.

Chenodeoxycholic acid

Chenodeoxycholic acid is white needles-like, mp 119 °C, almost insoluble in water, soluble in methanol and ethanol. This product is a gallstone dissolving agent which have dissolving effect on radiative and transparent cholesterol stones in functional gallbladder. By inhibiting the activity of hepatic β-hydroxy-β-methylglutaryl coenzyme A reductase, blocking the cholesterol biosynthesis, reducing the ratio of bile cholesterol to cholic acid, lowering the saturation of cholesterol, so that the stones will be dissolved for prevention the formation of new stones. In the bile of cholesterol gallstone patients, the ratio of chenodeoxycholic acid over other bile acid significantly decreases. The main metabolite of CDCA is lithocholic acid whose 3-sulfate vinegar conjugates secreted from bile to the intestines will be no longer reabsorbed. It can also be partially converted back to ursodeoxycholic acid through dehydrogenation of the 7-keto lithocholic acid.
For clinically treatment of cholelithiasis using chenodeoxycholic acid, use a daily dose of 15mg/kg. Long-term continuously oral administration has effect on dissolving gallstone or reducing its volume. It is especially suitable for treating high levels of cholesterol in gallstones, with diameter 1~2cm, smooth surface, and transparent cholelithiasis through X-ray. The gallstones of some patients relapse after stopping using. In addition, there are reports that this product can reduce triglyceride and cholesterol for patients of high blood serum. Adverse reactions include diarrhea and elevated level of serum transaminases.
The chemical structure of Chenodeoxycholic acid
Figure 1 The chemical structure of Chenodeoxycholic acid

Uses

anticonvulsant

Side effects

Has a small effect than chenodeoxycholic acid. It generally doesn’t cause diarrhea. Occasional occurrence of constipation, allergies, headaches, dizziness, pancreatitis, and tachycardia.

Choleretic drugs

Choleretic drugs are generally divided into two major categories: Choleretic agents and liquid-increase Choleretic agent. The former refers to the drug can promote the secretion of bile. The latter one refers only to those drugs which can increase capacity without increasing bile. The most commonly used Choleretic drugs is mainly cholic acid class-based such as sodium dehydroepiandrosterone acid, chenodeoxycholic acid and ursodeoxycholic acid and so on.
Ursodeoxycholic acid is a chemical agent of natural bile acid which is isolated from the bile of bear. It is the stereo-isomer of chenodeoxycholic acid. It has a similar litholysis effect, efficacy as chenodeoxycholic acid. However, it has a short course of treatment and a small dose. It is bound with taurine in the bile in vivo, and is a hydrophilic bile acids as well as a dissolving agent of cholesterol. It can reduce the secretion of cholesterol in the liver, lower the saturation content of cholesterol in bile, promote the secretion of bile acids, and increase the solubility of cholesterol in the bile so that cholesterol gallstones can be dissolved or prevented. Moreover, it can increase the secretion amount of bile, and have a choleretic effect by relaxing the bile duct mouth sphincter which smoothen the discharge of calculus. This product, however, cannot dissolve other types of gallstones. Ursodeoxycholic acid is useful in the treatment of cholesterol stones, hyperlipidemia, bile secretion disorders, primary biliary cirrhosis, chronic hepatitis, bile reflux gastritis and prevention of liver allograft rejection and reaction. The calculus-dissolving effect of this product is slightly weaker than the CDCA.

Drug Interactions

(1) In combination with chenodeoxycholic acid, the effect of promoting cholesterol level and de-saturation in bile were more than single drugs. The effect is also greater than that of the sum of the two drugs.
(2) This product is not suitable taken together with cholestyramine or antacids containing aluminum hydroxide for not affecting the absorption.
(3) Oral contraceptives may affect the efficacy of the product.

Pharmacological effects

Ursodeoxycholic acid, namely 3α, 7 β-dihydroxy bile acid, is the 7β-hydroxy epimer of chenodeoxycholic acid. Because of this small structural difference, the product is hydrophilic. It can reduce the activity of the rate-limiting enzyme in cholesterol synthesis in the liver--β-hydroxyl-β-methylglutaryl coenzyme A (HMG-CoA) reductase, thus inhibiting the cholesterol synthesis. It also forms a stable liquid crystalline suspension with cholesterol, and thus unsaturated the bile cholesterol, thereby promoting the separation and dissolution of cholesterol stone. This product can also inhibit the intestinal absorption of cholesterol. Ursodeoxycholic acid can also antagonize the cytotoxic effects of endogenous hydrophobic bile acids, protecting the liver cell membrane. By reducing the overexpression of the main membrane tissue compatibility antigen MHC-1, it can inhibit the production of interleukin-2,4, tumor necrosis factor and interferon α; and increasing the body's levels of interleukin-10,12; It also directly binds to the glucocorticoid receptor, playing a role in immune regulation. In addition, Ursodeoxycholic acid can also inhibit apoptosis, inhibit inflammation, scavenge free radical and have antioxidant effects. After oral administration, it is absorbed through non-ionic passive diffusion in the jejunum, and through active transport in the ileum. The effect of first-pass is large, 50% to 75% of the orally administrated dose is uptake by liver. It is mainly distributed in the liver, intestines and blood plasma, and has a 96% to 99% plasma protein binding rate. Ursodeoxycholic acid concentration in the bile exhibit dose-dependent increase; upon a dose of 20~30mg/(kg ? d), its concentration in bile is over 60%, reaching the best therapeutic effect. It binds to glycine, taurine in the liver, and is metabolized by intestinal. A small part of metabolite product is excreted from by urine, mostly by the fecal excretion. Biological half-life of oral administration is 3.5 to 5.8 days.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
InChI:InChI=1/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)/p-1/t14-,15-,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1

128-13-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma (U5127)  Ursodeoxycholic acid  ≥99% 128-13-2 U5127-25G 5,943.60CNY Detail
Sigma (U5127)  Ursodeoxycholic acid  ≥99% 128-13-2 U5127-5G 1,483.56CNY Detail
Sigma (U5127)  Ursodeoxycholic acid  ≥99% 128-13-2 U5127-1G 548.73CNY Detail
USP (1707806)  Ursodiol  United States Pharmacopeia (USP) Reference Standard 128-13-2 1707806-125MG 4,662.45CNY Detail
Sigma-Aldrich (Y0001163)  Ursodeoxycholic acid for system suitability  European Pharmacopoeia (EP) Reference Standard 128-13-2 Y0001163 1,880.19CNY Detail
Sigma-Aldrich (U0800000)  Ursodeoxycholic acid  European Pharmacopoeia (EP) Reference Standard 128-13-2 U0800000 1,880.19CNY Detail
Sigma-Aldrich (PHR1579)  Ursodiol  pharmaceutical secondary standard; traceable to USP, PhEur 128-13-2 PHR1579-500MG 791.15CNY Detail
Alfa Aesar (B20490)  Ursodeoxycholic acid, 99%    128-13-2 25g 4847.0CNY Detail
Alfa Aesar (B20490)  Ursodeoxycholic acid, 99%    128-13-2 5g 1277.0CNY Detail
Alfa Aesar (B20490)  Ursodeoxycholic acid, 99%    128-13-2 1g 408.0CNY Detail
TCI America (U0030)  Ursodeoxycholic Acid  >98.0%(GC)(T) 128-13-2 25g 1,990.00CNY Detail
TCI America (U0030)  Ursodeoxycholic Acid  >98.0%(GC)(T) 128-13-2 5g 650.00CNY Detail

128-13-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name ursodeoxycholic acid

1.2 Other means of identification

Product number -
Other names 3α,7β-Dihydroxy-5β-cholanic Acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:128-13-2 SDS

128-13-2Synthetic route

3α,7β-dihydroxy-5β-cholan-24-oic acid methyl ester
10538-55-3

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

ursodeoxycholic acid
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
7-Ketolithocholic acid
4651-67-6

7-Ketolithocholic acid

ursodeoxycholic 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

potassium 3,7-dioxo-5beta-cholanate

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; aluminum nickel In water98%
C24H36O4

C24H36O4

ursodeoxycholic acid
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%
7-Ketolithocholic acid
4651-67-6

7-Ketolithocholic acid

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

ursodeoxycholic acid
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

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

ursodeoxycholic acid
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

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

ursodeoxycholic 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

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

ursodeoxycholic acid
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

C26H36O4

ursodeoxycholic acid
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%
chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

ursodeoxycholic 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
Lithocholic acid
434-13-9

Lithocholic acid

A

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

B

3-keto-7β-hydroxy-5β-cholan-24-oic acid
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
3α,7β-dihydroxy-12-oxo-5β-cholane-24-oic acid
81873-91-8

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

ursodeoxycholic 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

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

ursodeoxycholic acid
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

7-ketochenodeoxycholic acid sodium salt

ursodeoxycholic acid
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

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

ursodeoxycholic acid
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%
methyl 3,7-dioxocholan-24-oate
7753-72-2

methyl 3,7-dioxocholan-24-oate

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
With ammonia; lithium In tetrahydrofuran; methanol at -50℃; for 1h;68%
methyl 3α-acetoxy-7-oxo-5β-cholan-24-oate
10452-65-0

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

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

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

chenodeoxycholic acid

A

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

B

7-Ketolithocholic acid
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%
3,7-diketocholanic acid
859-97-2

3,7-diketocholanic acid

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

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

7-Ketolithocholic acid

sodium ethanolate
141-52-6

sodium ethanolate

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
at 200℃;
3,7-diketocholanic acid
859-97-2

3,7-diketocholanic acid

aluminum isopropoxide
555-31-7

aluminum isopropoxide

isopropyl alcohol
67-63-0

isopropyl alcohol

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

methyl 3-O-acetyl-7-O-mesylchenodeoxycholate
81857-23-0

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

ursodeoxycholic acid
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

ursodeoxycholic acid
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

ursodeoxycholic acid
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;
hydrogenchloride
7647-01-0

hydrogenchloride

7-Ketolithocholic acid
4651-67-6

7-Ketolithocholic acid

acetic acid
64-19-7

acetic acid

platinum

platinum

A

chenodeoxycholic acid
474-25-9

chenodeoxycholic acid

B

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

Conditions
ConditionsYield
Hydrogenation;
[3H] Sodium glycoursodeoxycholate
92411-07-9

[3H] Sodium glycoursodeoxycholate

A

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

B

glycine
56-40-6

glycine

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

glycochenodeoxycholic acid sodium salt

ursodeoxycholic acid
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
sodium taurochenodeoxycholate
6009-98-9

sodium taurochenodeoxycholate

ursodeoxycholic acid
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
methyl 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oate
10538-64-4

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

ursodeoxycholic acid
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
N-Methyltaurine
107-68-6

N-Methyltaurine

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

3α,7β-dihydroxy-5β-cholan-24-oyl-N-methyltaurine

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%
methanol
67-56-1

methanol

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

3α,7β-dihydroxy-5β-cholan-24-oic acid methyl ester
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%
ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

acetic anhydride
108-24-7

acetic anhydride

(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
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%
ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

4-hydroxypropiophenone
70-70-2

4-hydroxypropiophenone

C33H48O5

C33H48O5

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

formic acid

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

(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
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%
ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

ferric ursodeoxycholate

ferric ursodeoxycholate

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

ursodeoxycholic acid

tauroursodeoxycholic acid sodium salt
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%
ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl 3α,7β-dihydroxy-5β-cholan-24-oate
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%
ursodeoxycholic acid
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
ethanol
64-17-5

ethanol

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

ethyl 3α,7β-dihydroxy-5β-cholan-24-oate
69519-36-4

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

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

ursodeoxycholic acid

2-aminoethanoic acid hydrochloride
6000-43-7

2-aminoethanoic acid hydrochloride

glycine ursodeoxycholic acid ethyl ester
115488-03-4

glycine ursodeoxycholic acid ethyl ester

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

ursodeoxycholic acid

acetyl chloride
75-36-5

acetyl chloride

3α,7β-dihydroxy-5β-cholan-24-oic acid methyl ester
10538-55-3

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

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

ursodeoxycholic acid

A

3,7-bis(sulfooxy)ursodeoxycholic acid
88426-32-8

3,7-bis(sulfooxy)ursodeoxycholic acid

B

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

7-(sulfooxy)ursodeoxycholic acid
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%
trimethyl-sulfo-ammonium betaine
63147-26-2

trimethyl-sulfo-ammonium betaine

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

ursodeoxycholic acid di-trimethylammonium 3,7-disulfate

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%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

N1<(3α,5β,7β)3,7-dihydroxy-24-oxo-cholan-24-yl>N4 methyl-piperazine
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%
ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

3-keto-7β-hydroxy-5β-cholan-24-oic 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
ursodeoxycholic acid
128-13-2

ursodeoxycholic acid

arabinosyl cytosine
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

(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;
pyrrolidine
123-75-1

pyrrolidine

ursodeoxycholic acid
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

(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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