700265 | Glycocholic acid

5β-cholanic acid-3α,7α,12α-triol N-(carboxymethyl)-amide

Glycocholic acid

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Glycocholic acid

5β-cholanic acid-3α,7α,12α-triol N-(carboxymethyl)-amide

Glycocholic Acid (Cholylglycine / N-Cholylglycine) is a crystalline bile acid (BA), found as a sodium salt in the bile of mammals. The metabolite is a conjugate of cholic acid, and its anions are called glycocholates.

Cholic acid is one of the two major BAs, together with chenodeoxycholic acid. They are the two most important human BAs, occurring at roughly equal concentrations in humans. Cholic acid molecules are insoluble in water and soluble in alcohol and acetic acid. The compound is widely used in the treatment of various BA synthesis disorders, caused by enzyme defects, peroxisomal disorders, steatorrhea, liver disease, etc.

Cholic acid derivatives, like Glycocholic Acid, are obtained from cholyl-CoA, which exchanges CoA with amino acids glycine or taurine. In this case, the conjugation with glycine that occurs in liver hepatocytes results in Glychocholic Acid. The conjugate can be synthesized from glycochenodeoxycholic acid, as well. More specifically, there are enzymes from the bacterial flora in the colon, involved with Glycocholic Acid synthesis. Associated microbial species are Bacterodes, Clostridium, Lactobacillus, and Bifidobacterium.

As a glycine conjugate of cholic acid, Glycocholic Acid has the ability to solubilize fats and other sterols for absorption and is also absorbed itself.

Glycholic acid is also used as an additional component in water-soluble and fat-soluble vitamin formulations, included in total parenteral nutrition. Its addition helps form a vitamin formulation that aids in the combination of many vitamins into one supplement.

Separate studies prove that Glycocholic Acid at a concentration of 1.6μmol/ml limits the expression of the gene that encodes farnesoid X receptor and increases genes encoding BA receptors such as TGR5 and S1PR2 which contribute to the normal flow of different metabolic pathways.

Glycocholic Acid has also been found to increase intracellular accumulation and cytotoxicity of anthracycline drug Epirubicin, used in chemotherapy.

Levels of Glycocholic Acid are elevated in the bile of patients with cholangiocarcinoma, compared to pancreatic cancer and benign biliary diseases. Serum concentrations of the metabolite are raised in patients with hepatocellular carcinoma as opposed to healthy individuals.

In addition, Glycocholic Acid hydrate has been the subject of studies to evaluate the invasiveness of Cryptosporidium spp. into cultured cells, and to assess the interaction between chitosan and oil-in-water emulsions under conditions triggering the digestive tract.

Avanti Polar Lipids follows the latest scientific standards to manufacture pure and effective lipid molecules, among which is Glycocholic Acid. So, purchase Avanti's Glycocholic Acid for successful research and development projects.

Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula

C26H43NO6

Percent Composition

C 67.07%, H 9.31%, N 3.01%, O 20.62%

Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
475-31-0
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
465.63
Exact Mass
465.31
Certificates of Analysis

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