Ursodeoxycholic acid

Catalog Number	ACM128132-2
CAS	128-13-2
Structure
Description	Ursodeoxycholic acid (INN, BAN and AAN), also known as ursodiol (USAN) and the abbreviation UDCA, from the root-word for bear urso, as bear bile contains the substance, is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria.
Synonyms	Tauroursodiol
IUPAC Name	(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]pentanoic acid
Molecular Weight	392.57
Molecular Formula	C24H40O4
Canonical SMILES	CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
InChI	InChI=1S/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)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
InChI Key	RUDATBOHQWOJDD-UZVSRGJWSA-N
Boiling Point	437.26 °C
Melting Point	203-204 °C(lit.)
Flash Point	9 °C
Purity	98%
Density	0.9985 g/cm³
Solubility	Practically insoluble in water
Appearance	Solid
Storage	2-8 °C
Complexity	605
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	10
EC Number	204-879-3
Exact Mass	392.29265975
Heavy Atom Count	28
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	3
Isomeric SMILES	C[C@H](CCC(=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
LogP	4.47790
MDL Number	MFCD00003680
Monoisotopic Mass	392.29265975
Physical State	Powder
Rotatable Bond Count	4
Stability	Stable under normal temperatures and pressures.
Storage Conditions	Store in a tightly closed container. Store in a cool, dry area away from incompatible substances.
Topological Polar Surface Area	77.8 Ų
WGK Germany	2

Knowledge & Learning Case Study Q&A

Ursodeoxycholic Acid for the Preparation of UDCA-PPG Nanoparticles

Zhou W, et al. Colloids and Surfaces B: Biointerfaces, 2024, 238, 113904.

Ursodeoxycholic acid (UDCA) was incorporated into polyethylene glycol (PEG)-polyethylenimine (PEI)-modified graphene oxide (GO) to create UDCA-PPG nanoparticles. These nanoparticles improved the solubility, dispersion, biocompatibility, and stability of UDCA.
Methodology:
To synthesize UDCA-PPG nanoparticles, 2.5 mL of 800 ng/mL PPG (using ultra-pure water as a solvent) was combined with 2.5 mL of 30 mM UDCA solution (consisting of 90% ultra-pure water and 10% TRIS-HCL at pH 8.8). The mixture was stirred overnight and subsequently collected after undergoing ultrafiltration membrane dialysis. Following the preparation of UDCA-PPG and PPG, the hydrodynamic size and morphology of the nanoparticles were determined using a particle size analyzer (Malvern Instruments Ltd, ZEN3600) and atomic force microscopy (AFM). The FTIR spectra of UDCA-PPG, PPG, and UDCA were then analyzed using an FT-IR spectrometer.

Ursodeoxycholic Acid in Non-Alcoholic Steatohepatitis (NASH) Treatment

Li H, et al. Biomedicine & Pharmacotherapy, 2024, 174, 116617.

Ursodeoxycholic acid (UDCA) is a hydrophilic bile acid primarily used to treat cholestatic liver diseases. This study explores the effects of high-dose UDCA on a mouse model of non-alcoholic steatohepatitis (NASH).
Methodology: Forty 6-week-old mice were fed a high-fat, high-cholesterol (HFHC) diet for 12 weeks to induce NASH. The mice were then divided into four groups: two groups transitioned to a normal diet, while the other two continued the HFHC diet. Each group received a daily dosage of 300 mg/kg of UDCA or saline for eight weeks. Fecal samples were collected for 16s ribosomal RNA gene sequencing, and serum bile acid profiles were analyzed using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS).
Findings: The study revealed that high-dose UDCA effectively reduced liver inflammation in NASH mice without significantly affecting liver fibrosis. UDCA treatment resulted in a notable shift in gut microbiota composition. Specifically, there was a reduction in the relative abundance of Bacteroides, Parabacteroides, and Intestinimonas, while norank_f_Muribaculaceae and Parasutterella increased in the HFHC diet groups. Additionally, UDCA altered the serum bile acid profile, increasing the total and primary bile acids while decreasing endogenous primary bile acids. A correlation analysis indicated a negative relationship between primary bile acids and the genera norank_f_Christensenellaceae and unclassified_f_Ruminococcaceae.
Conclusion: This study suggests that high-dose UDCA can alleviate liver inflammation in NASH by modifying gut microbiota composition and altering serum bile acid profiles. Although UDCA did not reduce liver fibrosis, its anti-inflammatory effects make it a promising candidate for further research in NASH treatment.

What is the molecular formula of Ursodeoxycholic acid?

The molecular formula of Ursodeoxycholic acid is C24H40O4.

What is the molecular weight of Ursodeoxycholic acid?

The molecular weight of Ursodeoxycholic acid is 392.6 g/mol.

What is another name for Ursodeoxycholic acid?

Another name for Ursodeoxycholic acid is ursodiol.

What is the role of Ursodeoxycholic acid in the body?

Ursodeoxycholic acid prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.

What is the IUPAC name of Ursodeoxycholic acid?

The IUPAC name of Ursodeoxycholic acid is (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]pentanoic acid.

What is the InChIKey of Ursodeoxycholic acid?

The InChIKey of Ursodeoxycholic acid is RUDATBOHQWOJDD-UZVSRGJWSA-N.

What is the canonical SMILES of Ursodeoxycholic acid?

The canonical SMILES of Ursodeoxycholic acid is CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C.

What is the DrugBank classification of Ursodeoxycholic acid?

Ursodeoxycholic acid is classified as a Bile Acid in DrugBank.

What is the CAS number of Ursodeoxycholic acid?

The CAS number of Ursodeoxycholic acid is 128-13-2.

How does the administration of Ursodeoxycholic acid affect bile composition?

The administration of Ursodeoxycholic acid changes the composition of bile and may dissolve gallstones.

Our products and services are for research use only and cannot be used for any clinical purposes.

Online Inquiry

Ursodeoxycholic acid (128-13-2)

Send A Message