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128-13-2

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128-13-2 Usage

Choleretic drugs

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.ursodeoxycholic acid structure

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 lookchem of Dai Xiongfeng.

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.

Side effects

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

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

Different sources of media describe the Chemical Properties of 128-13-2 differently. You can refer to the following data:
1. 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.
2. WHITE CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 128-13-2 differently. You can refer to the following data:
1. Ursodeoxycholic acid is a naturally occurring bile salt in humans. It is rapidly absorbed in the small intestine and excreted with the bile. Ursodeoxycholic acid is the drug of choise for the treatment of primary biliary cirrhosis and primary sclerosis cholanyitis. The daily dose amounts to 10-15 mg/kg. It has no side effects even after a treatment period of up to 20 years.Dissolution of gallstones. 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.Ursodeoxycholic acid 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. Ursodeoxycholic acid (UDCS) is a cell protectant used extensively to mitigate hepatic and biliary diseases. Ursodeoxycholic acid may be used to study its specific activities that range from reduction of cholesterol absorpition, cholesterol gallstone dissolution to suppression of immune response. It is also used as an anticholelithogenic. Epimer with Chenodiol with respect to the hydroxyl group at C7.

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%.

Originator

Actigall,Novartis

Definition

ChEBI: Ursodeoxycholic acid is 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. It has a role as a human metabolite and a mouse metabolite. It is a bile acid, a dihydroxy-5beta-cholanic acid and a C24-steroid. It is a conjugate acid of an ursodeoxycholate.

Manufacturing Process

Chenodeoxycholanic acid was dissolved in acetic acid and to this solution aqueous solution of CrO3 was added. As a result 3,7-diketodeoxycholanic acid was obtained, yield 95%, melting point 145°C. 15.0 g of 3,7-diketodeoxycholanic acid were dissolved in 80 ml of toluene, then petroleum ether 30 ml were added. 3,7-Diketodeoxycholanic acid as an oil precipitate was obtained, melting point 152°-154°C. 10.0 g of 3,7-diketodeoxycholanic acid were dissolved in 300 ml butanol, heated to 120°-130°C on bath and then sodium metallic 13.0 g were added. After that to this mixture hydrochloric acid was added for neutralization. Ursodeoxychlolanic acid was obtained, yield 9.4 g, melting point 193°C (recrystallization from ethyl acetate).

Brand name

Actigall (Watson); Urso (Axcan Scandipharm).

Therapeutic Function

Gallostone dissolving agent, Hepatoprotectant

General Description

Ursodeoxycholic acid (UDCA) is a secondary bile acid that helps regulate cholesterol. Mass spectrometry-based analysis of UDCA is routinely performed in clinical diagnostic testing applications such as neonatal testing of inborn errors of bile acid synthesis, differentiating among types of familial intrahepatic cholestasis, and therapeutic monitoring of patient responses to UDCA therapy. This Certified Spiking Solution? is suitable as a starting material in preparation of linearity standards, calibrators, and controls for use in LC-MS/MS and GC/MS bile acid testing methods.

Clinical Use

Dissolution of gallstonesUrsodeoxycholic acid or ursodiol is a naturally occurring bile acid that is used dissolve cholesterol gall stones and to treat cholestatic forms of liver diseases including primary biliary cirrhosis.

Drug interactions

Potentially hazardous interactions with other drugs Ciclosporin: unpredictably increases the absorption of ciclosporin in some patients.

Metabolism

Ursodeoxycholic acid is absorbed from the gastrointestinal tract and undergoes enterohepatic recycling. It is partly conjugated in the liver before being excreted into the bile. Under the influence of intestinal bacteria the free and conjugated forms undergo 7α-dehydroxylation to lithocholic acid, some of which is excreted directly in the faeces and the rest absorbed and mainly conjugated and sulphated by the liver before excretion in the faeces.

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 128-13-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 8 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 128-13:
(5*1)+(4*2)+(3*8)+(2*1)+(1*3)=42
42 % 10 = 2
So 128-13-2 is a valid CAS Registry Number.
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
  • TCI America

  • (U0030)  Ursodeoxycholic Acid  >98.0%(GC)(T)

  • 128-13-2

  • 5g

  • 650.00CNY

  • Detail
  • TCI America

  • (U0030)  Ursodeoxycholic Acid  >98.0%(GC)(T)

  • 128-13-2

  • 25g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (B20490)  Ursodeoxycholic acid, 99%   

  • 128-13-2

  • 1g

  • 408.0CNY

  • Detail
  • Alfa Aesar

  • (B20490)  Ursodeoxycholic acid, 99%   

  • 128-13-2

  • 5g

  • 1277.0CNY

  • Detail
  • Alfa Aesar

  • (B20490)  Ursodeoxycholic acid, 99%   

  • 128-13-2

  • 25g

  • 4847.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1579)  Ursodiol  pharmaceutical secondary standard; traceable to USP, PhEur

  • 128-13-2

  • PHR1579-500MG

  • 791.15CNY

  • Detail
  • Sigma-Aldrich

  • (U0800000)  Ursodeoxycholic acid  European Pharmacopoeia (EP) Reference Standard

  • 128-13-2

  • U0800000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001163)  Ursodeoxycholic acid for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 128-13-2

  • Y0001163

  • 1,880.19CNY

  • Detail
  • USP

  • (1707806)  Ursodiol  United States Pharmacopeia (USP) Reference Standard

  • 128-13-2

  • 1707806-125MG

  • 4,662.45CNY

  • Detail
  • Sigma

  • (U5127)  Ursodeoxycholic acid  ≥99%

  • 128-13-2

  • U5127-1G

  • 548.73CNY

  • Detail
  • Sigma

  • (U5127)  Ursodeoxycholic acid  ≥99%

  • 128-13-2

  • U5127-5G

  • 1,483.56CNY

  • Detail
  • Sigma

  • (U5127)  Ursodeoxycholic acid  ≥99%

  • 128-13-2

  • U5127-25G

  • 5,943.60CNY

  • 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%

128-13-2Related news

Original articleEffect of oral Ursodeoxycholic acid (cas 128-13-2) on cholelithiasis following laparoscopic sleeve gastrectomy for morbid obesity10/01/2019

BackgroundLaparoscopic sleeve gastrectomy (LSG) is a definitive solution for morbid obesity and its related co-morbidities. Cholelithiasis is a postoperative complication of LSG. The use of ursodeoxycholic acid (UDCA) after LSG is a proposed solution to reduce the incidence of cholelithiasis.detailed

Ursodeoxycholic acid (cas 128-13-2) is a GPBAR1 agonist and resets liver/intestinal FXR signaling in a model of diet-induced dysbiosis and NASH09/27/2019

Obeticholic acid (OCA) is a farnesoid-X-receptor (FXR) ligand, shown effective in reducing steatosis and fibrosis in NASH patients. However, OCA causes major side effects including pruritus, while increases the risk for liver decompensation in cirrhotic patients. Ursodeoxycholic acid (UDCA), is ...detailed

Original articleAdherence to Ursodeoxycholic acid (cas 128-13-2) therapy in patients with cholestatic and autoimmune liver disease09/24/2019

SummaryBackgroundUrsodeoxycholic acid (UDCA) is used for treatment of cholestatic liver diseases and may improve long-term outcome. Although treatment with this hydrophilic bile acid is virtually without side effects, medication adherence might be suboptimal due to patient misconceptions, compro...detailed

Anticholestatic mechanisms of Ursodeoxycholic acid (cas 128-13-2) in lipopolysaccharide-induced cholestasis09/10/2019

Lipopolysaccharide (LPS) from Gram (-) bacteria induces inflammatory cholestasis by impairing the expression/localization of transporters involved in bile formation (e.g., Bsep, Mrp2). Therapeutic options for this disease are lacking. Ursodeoxycholic acid (UDCA) is the first choice therapy in ch...detailed

Ursodeoxycholic acid (cas 128-13-2) and cancer: From chemoprevention to chemotherapy09/09/2019

Ursodeoxycholic acid (UDCA) is a secondary bile acid issued from the transformation of (cheno)deoxycholic acid by intestinal bacteria, acting as a key regulator of the intestinal barrier integrity and essential for lipid metabolism. UDCA is also a long-established drug, largely used for the diss...detailed

128-13-2Relevant articles and documents

Novel FXR (farnesoid X receptor) modulators: Potential therapies for cholesterol gallstone disease

Yu, Donna D.,Andrali, Sreenath S.,Li, Hongzhi,Lin, Min,Huang, Wendong,Forman, Barry M.

, p. 3986 - 3993 (2016)

Metabolic disorders such as diabetes are known risk factors for developing cholesterol gallstone disease (CGD). Cholesterol gallstone disease is one of the most prevalent digestive diseases, leading to considerable financial and social burden worldwide. Ursodeoxycholic acid (UDCA) is the only bile acid drug approved by FDA for the non-surgical treatment of gallstones. However, the molecular link between UDCA and CGD is unclear. Previous data suggest that the farnesoid X receptor (FXR), a bile acid nuclear receptor, may protect against the development of CGD. In studies aimed at identifying the role of FXR, we recently identify a novel chemical tool, 6EUDCA (6-αethyl-ursodeoxycholic acid), a synthetic derivative of UDCA, for studying FXR. We found that 6EUDCA binds FXR stronger than UDCA in a TR-FRET binding assay. This result was supported by computational docking models that suggest 6EUDCA forms a more extensive hydrogen bound network with FXR. Interestingly, neither compound could activate FXR target genes in human nor mouse liver cells, suggesting UDCA and 6EUDCA activate non-genomic signals in an FXR-dependent manner. Overall these studies may lead to the identification of a novel mechanism by which bile acids regulate cell function, and 6EUDCA may be an effective targeted CGD therapeutic.

Regioselective oxidation of cholic acid and its 7β epimer by using o-iodoxybenzoic acid

Dangate, Prasad S.,Salunke, Chetan L.,Akamanchi, Krishnacharya G.

, p. 1397 - 1399 (2011)

Rational exploration directed by DFT (density functional theory) based atomic Fukui indices, lead to development of regioselective oxidation of cholic acid and its 7β epimer by o-iodoxybenzoic acid. In case of cholic acid only, 7α-hydroxyl underwent oxidation, where as in its 7β epimer the selectivity was towards 12α-hydroxy group. Since these oxidations are the key steps in synthesis of ursodeoxycholic acid starting from cholic acid these findings may be useful in devising a protection free synthetic route.

Engineering Regioselectivity of a P450 Monooxygenase Enables the Synthesis of Ursodeoxycholic Acid via 7β-Hydroxylation of Lithocholic Acid

Grobe, Sascha,Badenhorst, Christoffel P. S.,Bayer, Thomas,Hamnevik, Emil,Wu, Shuke,Grathwol, Christoph W.,Link, Andreas,Koban, Sven,Brundiek, Henrike,Gro?johann, Beatrice,Bornscheuer, Uwe T.

, p. 753 - 757 (2021)

We engineered the cytochrome P450 monooxygenase CYP107D1 (OleP) from Streptomyces antibioticus for the stereo- and regioselective 7β-hydroxylation of lithocholic acid (LCA) to yield ursodeoxycholic acid (UDCA). OleP was previously shown to hydroxylate testosterone at the 7β-position but LCA is exclusively hydroxylated at the 6β-position, forming murideoxycholic acid (MDCA). Structural and 3DM analysis, and molecular docking were used to identify amino acid residues F84, S240, and V291 as specificity-determining residues. Alanine scanning identified S240A as a UDCA-producing variant. A synthetic “small but smart” library based on these positions was screened using a colorimetric assay for UDCA. We identified a nearly perfectly regio- and stereoselective triple mutant (F84Q/S240A/V291G) that produces 10-fold higher levels of UDCA than the S240A variant. This biocatalyst opens up new possibilities for the environmentally friendly synthesis of UDCA from the biological waste product LCA.

NAD+-Dependent Enzymatic Route for the Epimerization of Hydroxysteroids

Tonin, Fabio,Otten, Linda G.,Arends, Isabel W. C. E.

, p. 3192 - 3203 (2019)

Epimerization of cholic and chenodeoxycholic acid (CA and CDCA, respectively) is a notable conversion for the production of ursodeoxycholic acid (UDCA). Two enantiocomplementary hydroxysteroid dehydrogenases (7α- and 7β-HSDHs) can carry out this transformation fully selectively by specific oxidation of the 7α-OH group of the substrate and subsequent reduction of the keto intermediate to the final product (7β-OH). With a view to developing robust and active biocatalysts, novel NADH-active 7β-HSDH species are necessary to enable a solely NAD+-dependent redox-neutral cascade for UDCA production. A wild-type NADH-dependent 7β-HSDH from Lactobacillus spicheri (Ls7β-HSDH) was identified, recombinantly expressed, purified, and biochemically characterized. Using this novel NAD+-dependent 7β-HSDH enzyme in combination with 7α-HSDH from Stenotrophomonas maltophilia permitted the biotransformations of CA and CDCA in the presence of catalytic amounts of NAD+, resulting in high yields (>90 %) of UCA and UDCA.

7α-OH epimerisation of bile acids via oxido-reduction with Xanthomonas maltophilia

Medici, Alessandro,Pedrini, Paola,Bianchini, Ercolina,Fantin, Giancarlo,Guerrini, Alessandra,Natalini, Benedetto,Pellicciari, Roberto

, p. 51 - 56 (2002)

The microbial 7α-OH epimerisation of cholic, chenodeoxycholic, and 12-ketochenodeoxycholic acids (7α-OH bile acids) with Xanthomonas maltophilia CBS 827.97 to corresponding 7β-OH derivatives with scarcity of oxygen is described. With normal pressure of oxygen the 7-OH oxidation products are obtained. No biotransformations are achieved in anaerobic conditions. The microbial 7α-OH epimerisation is achieved by oxidation of 7-OH function and subsequent reduction. Partial purification, in fact, of the enzymatic fraction revealed the presence of two hydroxysteroid dehydrogenases (HSDH) α- and β-stereospecific together with a glycocholate hydrolase. On the basis of these results a further application is the microbial reduction of 6α-fluoro and 6β-fluoro-3α-hydroxy-7-oxo-5β-cholan-24-oic acid methyl esters to the corresponding 7α-OH and 7β-OH derivatives.

A Facile Route to Ursodeoxycholic Acid Based on Stereocontrolled Conversion and Aggregation Behavior Research

Dou, Qian,Jiang, Zhongliang

, p. 588 - 594 (2016)

A facile route to ursodeoxycholic acid (UDCA) and its aggregation behavior in aqueous phase solution, which is rarely known, are reported. The starting material, hyodeoxycholic acid (HDCA), is a relatively less expensive material and more easily obtained compared with chenodeoxycholic acid (CDCA). A facile route was developed to synthesize UDCA from HDCA with a Shapiro reaction as the key step and in 26% overall yield. A new strategy using organosilane reagent considering its stability, nontoxicity, and abundance in nature was carried out for a more rapid route and higher yield. It was found that the critical micelle concentration value, which is a critical value for surfactants of bile salts, was influenced by the number of hydroxyl groups.

Synthesis of ursodeoxycholic acid from plant-source (20S)-21-hydroxy-20-methylpregn-4-en-3-one

Gu, Xiang-Zhong,He, Li-Ming,Li, Chen-Chen,Qiu, Wen-Wei,Wang, Jie

, (2020)

A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from cheap and commercially available bisnoralcohol (BA). The key reaction conditions, including solvents, bases and reaction temperatures of the route were investigated and optimized. In the straightforward route for preparation of UDCA, most of the reaction steps have high conversions with average yields of 91%, and overall yield up to 59% (6 steps) from the plant-source BA. Especially in the last step of reduction and hydrolysis, there are five functional groups converted with calcd 97% per conversion in one-pot reaction. This promising route offers economical and efficient strategies for potential large-scale production of UDCA.

Microbial 7-OH epimerisation of bile acids

Dean, Mariangela,Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola,Poli, Silvia

, p. 693 - 694 (1999)

The microbial 7-OH epimerisation of cholic and chenodeoxycholic acids with Xanthomonas maltophilia CBS 827.97 to ursocholic and ursodeoxycholic acids with scarsity of oxygen is described. With normal pressure of oxygen the 7-ketocholic and the 7-ketochenodeoxycholic acids are obtained. No biotransformation is achieved in anaerobic conditions.

Purification method of ursodesoxycholic acid

-

Paragraph 0071-0082, (2021/10/11)

The invention discloses a purification method of ursodesoxycholic acid. The purification method comprises the following steps: step A, preparing 4-dimethyl pyridine ammonium salt of ursodesoxycholic acid; and step B, performing hydrolysis of 4-dimethyl pyridine ammonium salt of ursodesoxycholic acid. The method is simple and convenient to operate, the used solvent and reagent are cheap and easy to obtain, the method is suitable for industrial production, and the obtained ursodesoxycholic acid is high in purity.

A method of synthesis of ursodesoxycholic acid(UDCA) using bile salt hydrolase(BSH) from Porcine intestinal flora Bifidobacterium thermophilum

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Paragraph 0045-0046, (2020/07/11)

The present invention relates to a method for synthesizing ursodesoxycholic acid (UDCA) from porcine bile acid by using bile salt hydrolase (BSH) derived from Bifidobacterium thermophilum in porcine gut microbiota. The present inventors have found that, compared to existing synthesis methods involving repeated purification processes, an UDCA synthesis method using the BSH of Bifidobacterium thermophilum in porcine gut microbiota is simple and time-saving; provides remarkable advantages in terms of high-throughput production and stability; is significantly more economical; and can increase an UDCA yield. In addition, the present invention is expected to provide a significant economic advantage in that it provides high-value added UDCA effective in improving hepatic functions, alleviating fatigue through liver improvement, cholesterol reduction, gallstone dissolution, primary biliary cirrhosis, and the like by utilizing porcine waste by-products.(AA) First step : Extract bile acid derived from by-products(BB) Second step : Extract BSH enzyme(CC) Third step : Extract CDCA(DD) Fourth step : Synthesize and purify UDCA(EE) Fifth step : Analyze UDCA(FF) Process of extracting bile acid for use in UDCA synthesis in by-products, Extract bile acid soluble by use of organic solvent methanol and evaporate methanol to obtain bile acid(GG) Extract BSH enzyme by expression and purification of BSH from lactic acid bacteria having BSH enzyme used in CDCA extraction(HH) Extract bile acid from CDCA as a measure to increase the purity and yield of UDCA from extracted bile acid(II) Synthesize UDCA by redox reaction using CDCA from the bile acid extracted from respective by-products(JJ) Analyze CLA via HPLC in order to confirm the synthesis and yield of synthesized UDCACOPYRIGHT KIPO 2020

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