Tauroursodeoxycholic acid

Catalog Number	ACM14605222-2
CAS	14605-22-2
Structure
Synonyms	TUDCA Soduim salt
IUPAC Name	2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
Molecular Weight	499.7
Molecular Formula	C26H45NO6S
Canonical SMILES	CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
InChI	InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1
InChI Key	BHTRKEVKTKCXOH-LBSADWJPSA-N
Boiling Point	496.4ºC at 760mmHg
Melting Point	173-175 °C
Flash Point	214.2 °C
Purity	95%
Density	1.216±0.06 g/cm³
Appearance	White solid
Storage	15-30 °C
Complexity	858
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	10
Exact Mass	499.29675933
Heavy Atom Count	34
Hydrogen Bond Acceptor Count	6
Hydrogen Bond Donor Count	4
Isomeric SMILES	C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
Monoisotopic Mass	499.29675933
Rotatable Bond Count	7
Topological Polar Surface Area	132 Ų
WGK Germany	2

Knowledge & Learning Case Study Q&A

Therapeutic Potential of Tauroursodeoxycholic Acid (TUDCA) in Liver Health

Baba B, et al. Archives of Gerontology and Geriatrics, 2024, 125, 105517.

Tauroursodeoxycholic acid (TUDCA) is known for its cytoprotective and anti-inflammatory properties, particularly in liver disorders. This study investigates the combined effects of TUDCA and SCD Probiotics on liver health in elderly male Sprague-Dawley rats. The study evaluates the biomolecular composition, histopathological changes, and inflammasome activity in the liver following treatment.
Methodology: Elderly male Sprague-Dawley rats were administered intravenous TUDCA (300 mg/kg) and oral SCD Probiotics daily for one week. Analytical techniques included ATR-FTIR spectroscopy integrated with machine learning to assess biomolecular structures, RT-qPCR for quantifying inflammasome markers (NLRP3, ASC, Caspase-1, IL18, IL1β), and histological examinations for liver pathology.
Results
Lipid Metabolism: TUDCA significantly enhanced lipid metabolism by reducing cholesterol esters. SCD Probiotics modulated lipid and protein profiles, notably affecting fatty acid chain lengths and protein configurations.
Histopathology: Both treatments resulted in significant reductions in cellular degeneration, lymphatic infiltration, and hepatic fibrosis. Histological analysis indicated improved liver morphology.
Inflammasome Activity: TUDCA and SCD Probiotics reduced the expression of inflammasome-related genes, including NLRP3 and ASC. This suggests a suppression of inflammasome activity, which is associated with decreased liver inflammation and fibrosis.
Biochemical Markers: SCD Probiotics paradoxically increased AST and LDH levels, indicating potential liver stress, while exclusively elevating albumin levels, suggesting a protective effect against liver damage.
Conclusion: TUDCA's role in improving lipid profiles and reducing cholesterol esters, coupled with SCD Probiotics' modulation of fatty acids and protein structures, highlights their therapeutic synergy. Both agents effectively reduce liver inflammation and fibrosis, though SCD Probiotics may introduce some stress markers.

Tauroursodeoxycholic Acid for the Preparation of TUDCA/Emodin liposomes

Zhao J, et al. Colloids and Surfaces B: Biointerfaces, 2024, 236, 113798.

Amphiphilic bile acid, tauroursodeoxycholic acid (TUDCA), can be used as a substitute for cholesterol (CHL) in traditional liposomes to create TUDCA/Emodin liposomes. The results indicated that these TUDCA/Emodin liposomes demonstrated uniform particle size distribution, good stability, low cytotoxicity, enhanced mucus permeability, and anti-inflammatory activity. Additionally, they provided cellular protection against oxidative stress.
Preparation of TUDCA/Emodin Liposomes:
All TUDCA liposomes were prepared using the thin film hydration method. The ratios of soybean lecithin to TUDCA and emodin were 3:1 and 30:1, respectively. In brief, soybean lecithin, TUDCA, and emodin were dissolved in 4.0 mL of ethanol and evaporated to form a thin film on the inner walls of a flask at 50°C. Sterile deionized water was then added, and the flask was rotated at 50°C to hydrate the film. The resulting dispersion was filtered using a 0.22 µm PES membrane and subsequently extruded 15 times through a liposome extruder. The preparation of cholesterol liposomes followed the same procedure, substituting cholesterol for TUDCA.

What is the molecular formula of tauroursodeoxycholic acid?

The molecular formula of tauroursodeoxycholic acid is C26H45NO6S.

What is the molecular weight of tauroursodeoxycholic acid?

The molecular weight of tauroursodeoxycholic acid is 499.7 g/mol.

What is the PubChem CID of tauroursodeoxycholic acid?

The PubChem CID of tauroursodeoxycholic acid is 9848818.

What is the IUPAC name of tauroursodeoxycholic acid?

The IUPAC name of tauroursodeoxycholic acid is 2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid.

What is the InChI of tauroursodeoxycholic acid?

The InChI of tauroursodeoxycholic acid is InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1.

What is the Canonical SMILES of tauroursodeoxycholic acid?

The Canonical SMILES of tauroursodeoxycholic acid is CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C.

What is the CAS number of tauroursodeoxycholic acid?

The CAS number of tauroursodeoxycholic acid is 14605-22-2.

What is the UNII of tauroursodeoxycholic acid?

The UNII of tauroursodeoxycholic acid is 60EUX8MN5X.

What is the ChEMBL ID of tauroursodeoxycholic acid?

The ChEMBL ID of tauroursodeoxycholic acid is CHEMBL272427.

Is tauroursodeoxycholic acid a natural product found in Homo sapiens?

Yes, tauroursodeoxycholic acid is a natural product found in Homo sapiens.

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