700199 | Ursodeoxycholic acid

5β-cholanic acid-3α,7β-diol


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Ursodeoxycholic acid

Ursodeoxycholic acid

5β-cholanic acid-3α,7β-diol

An epimer of chenodeoxycholic acid, Ursodeoxycholic acid (UDCA), or ursodiol is a mammalian secondary bile acid, a product of the intestinal bacteria metabolism, that has a wide range of applications in clinical trial and research.

Common depositor-supplied synonyms are:

  • Actigall
  • Ursofalk
  • Ursolvan
  • Delursan
  • Ursobilin
  • Ursodamor
  • Deursil
  • Ursacol
  • Ursosan
  • Lyeton
  • Peptarom
  • Urosiol

The microbiota within the colon produces epimerizing enzymes that prompt epimerization of the conjugated primary chenodeoxycholic bile. 

It’s a process that comprises two steps: 

  1. 1. Oxidation 
  2. 2. Stereospecific reduction 

The result is the formation of UDCA. Ursodiol is the major type of bacterial metabolite in the large intestine, alongside short-chain fatty acids.

UDCA holds an established role in a variety of processes in the human body.

The compound is proven to regulate cholesterol metabolism and homeostasis. The exact mechanism of its action is not completely understood. However, it is believed that UDCA decreases biliary cholesterol in 2 ways:

  • - UDCA inhibits hepatic cholesterol production and secretion.
  • - UDCA suppresses the absorption of cholesterol in the intestines.

This leads to reduced biliary cholesterol levels resulting in gradual cholesterol solubilization from gallstones and their eventual dissolution. So, UDCA might even prevent gallstone formation. Additionally, ursodiol has been shown to reduce serum total and low-density lipoprotein (LDL).

Ursodeoxycholic acid is essential for lipid metabolism since it accelerates the digestion and absorption of lipids in the gut. That also appears to decrease LDL catabolism.

The anticholestatic abilities of ursodeoxycholic acid suggest that it has positive effects on intrahepatic cholestasis, even primary biliary cholangitis, and other hepatobiliary disorders, as well as chronic hepatitis. 

Anticholestatic effects of ursodiol have also been reported in intrahepatic cholestasis occurring during pregnancy, cystic fibrosis liver disease, and progressive familial intrahepatic cholestasis.

In addition, UDCA shows favorable effects on liver cells and liver enzyme levels by facilitating the bile flow through the liver.

The beneficial effects of the product are believed to be due to its well-established antioxidant, anti-inflammatory, and cytoprotective properties. It’s shown to prevent oxidative stress in the kidneys of diabetic mice. 

Recently, ursodeoxycholic acid has been the subject of research on its anticancer effects with persuasive outcomes that it reduces experimentally induced liver and colon carcinogenesis in rats.

The tauro-conjugated form of ursodiol shows neuroprotective potential in animal models of frontotemporal dementia, Huntington’s disease, and other neurological conditions.

Recent studies reveal that bile acids act additionally as signaling ligands for receptors such as G-protein-coupled bile acid receptor and Farnesoid X receptor to modulate and improve metabolism of glucose and energy, as well. Thus, ursodiol alongside other bile acids is emerging as a key regulator of glucose homeostasis.

Choose Avanti Polar Lipids to provide you with the highest quality Ursodeoxycholic acid products for your studies.

Hygroscopic
No
Light Sensitive
No
Molecular Formula

C24H40O4

Percent Composition

C 73.43%, H 10.27%, O 16.30%

Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
128-13-2
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
392.580
Exact Mass
392.290