Ursodeoxycholic acid

Product information

 

Ursodeoxycholic acid Basic information

Choleretic drugs Pharmacological effects Chenodeoxycholic acid Drug Interactions Adverse reactionsPrecautions Determination of the content ursodeoxycholic acid and chenodeoxycholic acid in bear bile by TLCS method Chemical Properties Application Production method

Product Name:	Ursodeoxycholic acid
Synonyms:	7BETA-HYDROXYLITHOCHOLIC ACID;6BETA-CHOLANIC ACID-3A,7BETA-DIOL;(6-BETA)-CHOLANIC ACID-(3-ALPHA)-(7-BETA)-DIOL;3A,7B-DIHYDROXY-5B-CHOLAN-24-OIC ACID;3ALPHA, 7BETA-DIHYDROXY-5BETA-CHOLANIC ACID;3ALPHA,7BETA-DIHYDROXY-5BETA-CHOLAN-24-OIC ACID;3alpha,7beta-dihydroxy-6beta-cholan-24-oic acid;3ALPHA, 7BETA-DIOXYCHOLANIC ACID
CAS:	128-13-2
MF:	C24H40O4
MW:	392.57
EINECS:	204-879-3
Product Categories:	Bile Acids;Biochemistry;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;API's;API;Herb extract;DEPACON;BPC;Inhibitors
Mol File:	128-13-2.mol

Ursodeoxycholic acid Chemical Properties

mp	203-204 °C(lit.)
alpha	60 º (c=2, EtOH)
refractive index	60.5 ° (C=2, EtOH)
storage temp.	Refrigerator
solubility	ethanol: 50 mg/mL, clear
Water Solubility	practically insoluble
Merck	14,9889
CAS DataBase Reference	128-13-2(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	24/25-36-26
WGK Germany	2
RTECS	FZ2000000
F	10

MSDS Information

Provider	Language
3alpha,7beta-Dihydroxy-6beta-cholan-24-oic acid	English
ACROS	English
SigmaAldrich	English
ALFA	English

Ursodeoxycholic acid Usage And Synthesis

Determination of the content ursodeoxycholic acid and chenodeoxycholic acid in bear bile by TLCS method	(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  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 Figure 3 The content of ursodeoxycholic acid and chenodeoxycholic acid in bear bile
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.
Application	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.
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%.

 

 

Company information

 Henan sunlake enterprise corporation is located in Henan Province , The central plain of China , Which enjoys favorable geogeaphical position and convenient transportion, The com[any was established in june. 1998 , until now having more than 18 years experience in manufacturing & exporting chemical raw material .

  Sunlake is a professional manufacturer engaged in producing and selling chemicals,including Organic & inorganic chemicals , pigments & Dyestuffs ,  Water treatment chemicals , Food & FEED additives and others . these products have been being well exported to europe , southeast Asia , the Middle East ,  Africa , South America and some other countries and areas.

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