丨
Tauroursodeoxycholic acid
| Chinese Name | 牛磺熊去氧胆酸 |
| Chinese Synonyms | 牛磺熊去氧胆酸(牛磺脱氧胆酸,牛熊去氧胆酸钠,牛磺酸熊脱氧胆酸,牛磺熊脱氧胆酸钠盐,牛磺酸熊去脱氧胆酸); 牛磺雄去氧胆酸;牛磺熊脱氧胆酸;牛磺熊去氧胆酸Chemicalbook(牛磺熊脱氧胆酸);牛熊去氧胆酸;牛磺酸熊去脱氧胆酸; TAUROURSODEOXYCHOLICACID牛磺熊去氧胆酸;牛磺熊去氧胆酸标准品;牛磺熊去氧胆酸 |
| English Name | Tauroursodeoxycholic acid |
| English Synonyms | ursodeoxycholyltaurine;yl)amino)-;3a,7b-Dihydroxy-5b-cholan-24-oicAcidN-(2-Sulfoethyl)amide;Ursodeoxycholyltaurin; 3α,7β-dihydroxChemicalbooky-5β-cholan-24-oicacidn-(2- sulfoethyl)amide;TUDCASoduimSalt;TAUROURSODEOXYCHOLICACIDDIHYDRATE:90%;tauroursodeoxycholicacidsodium |
| CAS | 14605-22-2 |
| Molecular Formula | C26H45NO6S |
| Molecular Weight | 499.7 |
| EINECS | 1308068-626-2 |
| Related Categories | Reference substance; Cholic acid series; Pharmaceutical raw materials; Standard products; Detergent; Chinese medicine reference substance; Standard and reference materials; Biochemical reagents; Other reagents; Active pharmaceutical ingredients; Plant extracts; Raw materials; Small molecule inhibitors; Small molecule inhibitors, natural products; Animal extracts; Chinese herbal ingredients; intermediate; Pharmaceutical raw materials; Health product additives; Digestive system related; Analytical reagent standards; API for active pharmaceutical ingredients; Other raw materials; Reference standard – Chinese medicine reference standard; Standard products – Chinese medicine standard products; Other terpenoids; Analytical reagents – reference standards; Medical raw materials; Intermediate of synthetic materials; Pharmaceutical and organic synthesis intermediates; Pharmaceutical raw materials; Chemical raw materials; Impurity reference standard; Dye intermediates; Organic chemical raw materials; MiscellaneousNaturalProducts; BileAcids; Biochemistry; Steroids; ChiralReagents; Inhibitors; Intermediates&FineChemicals; Pharmaceuticals; Herbextract; Research materials; Raw material intermediates; Products with pictures; Chemical Reagents; Clinical testing standard substances; chemical intermediate |
| Mol File | 14605-22-2.mol |
| Structural Formula | 14605-22-2 |
丨
Tauroursodeoxycholic acid [Properties]
| Melting Point | 173-175°C |
| Density | 1.216±0.06 g/cm3(Predicted) |
| Refractive Index | 46 ° (C=1, EtOH) |
| Storage Conditions | 15-25℃ |
| Solubility | Soluble in DMSO (up to 30mg/ml) or ethanol (up to 20mg/ml when heated) |
| Form | solid |
| Acidity Coefficient (pKa) | 1.42±0.50(Predicted) |
| Color | white |
| Stability | Maintain stability within one year from the date of purchase. DMSO or ethanol solution can be stored at -20 ° C for up to one month. |
| Main Applications | lipidomics |
| InChIKey | BHTRKEVKTKCXOH-LBSADWJPSA-N |
| SMILES | [C@@]12([H])CCC@HNCCS(=O)(=O)O)[C@@]1(C)CC[C@]1([H])[C@@]3(C)CCC@@HC[C@@]3([H])CC@H[C@@]21[H] |&1:0,4,5,18,22,24,28,31,34,36,r| |
| CAS Database | 14605-22-2(CAS DataBase Reference) |
| CAS Number Unlabeled | 35807-85-3 |
丨
Tauroursodeoxycholic acid Application and synthesis method
Introduction
Tauroursodeoxycholic acid is the main effective component of bear bile and also the main component of synthetic bear bile. It is a conjugated bile acid that widely exists in human and various animal bile and has a variety of physiological and pharmacological effects. This drug and its preparations have 20 years of clinical experience in marketing abroad, and are mainly used for steroidal gallbladder chemobooks stones, cholestatic liver diseases (such as primary biliary cirrhosis), bile reflux gastritis, autoimmune hepatitis (AIH), primary biliary cirrhosis (PBC), and primary sclerosing cholangitis (PSC C). Chronic hepatitis (hepatitis B, hepatitis C, etc.), alcoholic fatty liver, non-alcoholic fatty liver, drug-induced liver damage, prevention and treatment complications before and after liver transplantation.
Purpose
Ursodeoxycholic acid has antispasmodic, anticonvulsant, anti-inflammatory, and cholelithiasis dissolving effects. It is mainly used clinically to treat gallbladder cholesterol stones, primary sclerosing cholangitis, primary biliary cirrhosis, and chronic hepatitis C.
Drug action and clinical application
Sodium taurochodeoxycholic acid, also known as taurochodeoxycholic acid or taurochodeoxycholic acid, with the chemical name 3 α, 7 β dihydroxycholanyl-N-Taurine, is mainly present in black bear bile and is a characteristic active ingredient in bear bile. Has antispasmodic, anticonvulsant, anti-inflammatory, and cholelithiasis dissolving effects.
The modern synthetic drug taurodeoxycholic acid is a conjugated bile acid formed by the condensation between the acetyl group of ursodeoxycholic acid and the amino group of taurine. Ursodeoxycholic acid capsules have been launched overseas and were approved for sale in China as an imported drug in 2007. They are mainly used clinically to treat gallbladder cholesterol stones, primary sclerosing cholangitis, primary biliary cirrhosis, and chronic hepatitis C. At present, there is no drug registration for taurodeoxycholic acid raw materials and their preparations in China.
Sodium taurodeoxycholic acid is a natural bile acid isolated from bear bile. It belongs to a chemical preparation and exists in bile in combination with taurine in the body. It is a hydrophilic bile acid and a cholesterol stone dissolving agent. It can reduce the secretion of cholesterol by the liver, lower the saturation of cholesterol in bile, promote the secretion of bile acids, increase the solubility of cholesterol in bile, dissolve cholesterol stones or prevent the formation of stones. It can increase the secretion of bile, relax the sphincter muscle of the bile duct, and produce a choleretic effect, which is beneficial for the expulsion of stones. This product cannot dissolve other types of gallstones. Suitable for treating cholesterol stones, hyperlipidemia, bile secretion disorders, primary biliary cirrhosis, chronic hepatitis, bile reflux gastritis, and preventing acute rejection and reactions in liver transplantation. The stone dissolving effect of this product is slightly weaker than that of chenodeoxycholic acid.
Preparation
1) The preparation of crude taurodeoxycholic acid is carried out according to the following steps:
In the reaction vessel, 4.0KG of ursodeoxycholic acid was added, 19KG of acetone was added, and 1650ml of triethylamine was added while stirring. The jacket refrigeration was turned on to lower the temperature of the mixture to -10 ℃. 1120ml of ethyl chloroformate was added and the addition rate was controlled to maintain the temperature of the reaction solution between -5-0 ℃. After 30 minutes, the mixture was added and stirred for another 40 minutes to obtain a mixed anhydride of ursodeoxycholic acid and ethyl chloroformate. The mixed anhydride reaction solution was filtered through a filter with nitrogen gas into a 50 liter reaction vessel containing 4.2KG of purified water, 1.4KG of taurine, and 0.4KG of sodium hydroxide. The reaction was thoroughly stirred for 3 hours to obtain 4.0KG of crude taurodeoxycholic acid.
2) The refinement of crude taurodeoxycholic acid is carried out according to the following steps:
(1) Put 4.0KG of Ursodeoxycholic acid taurosulfonate into a 50L reaction kettle, add 4KG of water and 580ml of acetone, heat and stir until completely dissolved;
(2) Cool to -5-0 ℃ while stirring, and crystallize for 30 hours;
(3) Put the material into the filter and filter it. After draining, rinse the filter cake with ice water (-3-0 ℃) and then drain it again to obtain 3.3KG of taurodeoxycholic acid (purity 99.6%), HPLC)， The content of taurodeoxycholic acid is 0.3%, and the maximum content of other impurities is 0.05% (determined by liquid chromatography).
Bioactivity
Tauroursodeoxycholic acid (TUDCA) is a taurine conjugate of ursodeoxycholic acid, which can serve as a mitochondrial stabilizer and anti apoptotic agent in various neurodegenerative diseases such as Alzheimer’s disease, Parkinson’s disease, and Huntington’s disease.
Target
ERK Caspase-3 Caspase-12 Human Endogenous Metabolite
In vitro study
Tauroursodeoxycholate(TUDCA)suppressesbothviabilityandmigrationofvascularsmoothmusclecells(VSMCs)throughinhibitionofERKphosphorylation,byinductionofmitogen-activatedproteinkinasephosphatase-1(MKP-1)viaPKCα.TauroursodeoxycholateinhibitsboththeproliferationandmigrationofVSMCsviainhibitionofERK,throughCa2+-dependentPChemicalbookKCαtranslocation.Tauroursodeoxycholatepreventsplatelet-derivedgrowthfactor(PDGF)andvascularinjury-inducedMMP-9expression.Theknock-downofMKP-1usingspecificsi-RNArestoresthereducedVSMCviabilitybyTauroursodeoxycholate(200μM),whichsuggeststhatanti-proliferativeeffectofTauroursodeoxycholatedependedontheMKP-1expression.
In vivo research
TheeffectsofTauroursodeoxycholate(TUDCA)onproliferationandapoptosisofVSMCsinvivoareexaminedusingimmunohistochemistryforproliferatingcellnuclearantigen(PCNA)andthetransferasedUTPnick-endlabelling(TUNEL)assay.Tauroursodeoxycholate(10,50,and100mg/kg)increasesthecaspase3activityofinjuredtissuesinadose-dependentmanner,indicatingthatTauroursodeoxycholateinducesapoptosisofVSMCsintheneointima.Usingtheinjuredtissues,furtherexaminationandcomparisonofthephosphorylationlevelofERKandMMP-9expressionisperformedat1weekafterinjury,comparedwithnormalcontrols.BallooninjuryincreasedboththephosphorylationofERKandexpressionofMMP-9inthetissues.Tauroursodeoxycholate(10,50,and100mg/kg)inhibitsphosphorylationofERKandMMP-9expressioninadose-dependentmanner.Tauroursodeoxycholate(TUDCA)isahydrophilicbileacid.TauroursodeoxycholateasacytoprotectiveagentimprovesliverfunctionandcanpreventhepatocellularcarcinomabyreducingERstressandapoptosis.TauroursodeoxycholatesChemicalbookignificantlyreducesexpressionofapoptosismolecules,suchascaspase-3,caspase-12,C/EBPhomologousprotein,c-JunN-terminalkinase(JNK),activatingtranscriptionfactor4(ATF4),X-boxbindingprotein(XBP),andeukaryoticinitiationfactor2α(eIF2α)inAngIIinducedApoE-/-mice(p<0.05).TauroursodeoxycholatereducesAngiotensin(Ang)IIinducedabdominalaorticaneurysm(AAA)formationinApoE-/-mice.Tauroursodeoxycholateisusedatadoseof0.5g/kg/dayintreatingAngIIinducedApoE-/-mice(ERstressinhibitorgroup).Systolicbloodpressure(141.3±5.6mmHgvs145.9±8.9mmHg;p>0.05)andtotalcholesterollevels(663.6±88.7mg/dLvs655.7±65.4mg/dL;p>0.05)donotdifferbetweentheAAAmodelgroupandTauroursodeoxycholategroup.Inaddition,maximumaorticdiameterissignificantlysmallerinthoseinTauroursodeoxycholategroupcomparedwiththoseintheAAAmodelgroup(0.95±0.03mmvs1.79±0.04mm;p<0.05).AAAlesionareasarealsosmallerinthoseinTauroursodeoxycholategroupthaninthoseintheAAAmodelgroup(0.37±0.03mm2vs1.51±0.06mm2;p<0.05).
Purpose
Biochemical research; Lipase accelerator; Anion remover, used for protein dissolution; Preparation of bacterial culture medium (intestinal bacterial culture and isolation)
Purpose
Used for content determination/identification/pharmacological experiments, etc.
丨
Safety Information
| Safety Instructions | 22-24/25 |
| WGK Germany | 2 |
| RTECS | KI7372500 |
| HS Code | 29242990 |
| Storage category | 11 – Combustible solid |
| Toxicity | mouse,LD50,intravenous,350mg/kg (350mg/kg),Japanese Kokai Tokyo Koho Patents. Vol. #92-235918, |
丨
MSDS Information
丨
Tauroursodeoxycholic acid Price (reagent grade)
| Update Date | Product Number | Product Name | CAS | Package | Price |
| 2025/12/22 | T1567 | 牛磺脱氧胆酸 二水合物 Tauroursodeoxycholic Acid Dihydrate | 14605-22-2 | 1g | ￥210 |
| 2025/12/22 | T1567 | 牛磺脱氧胆酸 Tauroursodeoxycholic Acid Dihydrate | 14605-22-2 | 5g | ￥730 |
