Cholic Acid (Cholate)
Cholic acid is one of the most abundant bile acids in humans. Cholic acid is usually conjugated in amide linkage with the amino acids glycine or taurine, yielding glycocholate and taurocholate, respectively. Cholic acid is sparingly soluble in water. Soluble in glacial acetic acid and some organic solvents.
In nature, cholic acid is produced in the liver from cholesterol. The liver converts cholesterol into the conjugated salts of glycocholic and taurocholic acid which are excreted into the bile. Bile is released into the intestine where the bile salts emulsify fats and promote digestion. About 90% of the bile salts are reabsorbed by the intestine and pass back to the liver by a process referred to as enterohepatic circulation.
Bile salts play important roles in emulsification of fat in the digestion process. Bile salts are detergent-like substances secreted from the gallbladder that aid in the digestion and absorption of lipids. A bile salt is made up of a bile acid and an associated cation, usually an amino acid. Examples include glycocholate and taurocholate.
The main use of cholic acid is as an intermediate for the production of ursodeoxycholic acid. Ursodeoxycholic acid is a pharmaceutical product which is used for several indications including the dissolution of gall stones and the treatment and prevention of liver disease.
Cholic acid has many different uses in traditional Chinese medicine. Its main use is as an ingredient in the manufacture of artificial calculus bovis (artificial gall stones).
Like a detergent, bile salts contain hydrophobic and hydrophilic components. The hydrophobic portions of the molecule associate with the fat, and the hydrophilic parts associate with water, serving to solubilize (emulsify) the otherwise insoluble fat.
Cholic acid is a family of steroids comprising the bile acids (or salts), generally in conjugated form (e.g., glycocholic and taurocholic acids). Chemically, cholic acids are cholan-24-oic (cholanic) acids (the terminal C24 of cholane becoming a -COOH group); biologically, cholic acids are derived from cholesterol (a cholestane derivative) and display varying degrees of oxidation (OH groups) and orientation at positions 3, 7, and 12. It is these oxidations and orientations that distinguish the several cholic acid; e.g., cholic acid is 3a,7a,12a-trihydroxy-5b-cholan-24-oic acid, deoxycholic acid is 3a,12a-dihydroxy-5b-cholanic acid.
Bile acids are derived from cholesterol and have detergent properties which aid in fat digestion and absorption. Bile acid synthesis is the major metabolic end product of cholesterol, accounting for about half of the 800 mg/day that is made in the body. By contrast, synthesis of steroid hormones from cholesterol requires only about 50 mg/day of cholesterol. Although the body synthesizes about 400 mg of bile acids per day, closer to 20-30g of bile acids per day are secreted into the upper small intestine. To meet this need, the body recycles bile acids from the lower small intestine to the liver via enterohepatic circulation.
Bile acids are eliminated in the feces but, due to recycling, only about 0.5g/day or less are eliminated in this way.
Cholic acid and chenodeoxycholic acid are the predominant bile acids in humans. The bile acid deoxycholate is abundant in the bile of some other mammals. Conjugates of cholic acid with glycine and taurine form salts called glycocholate and taurocholate, respectively.
Synonym: cholalic acid, cholanic.
Molecular Weight: 408
CAS Number: 81-25-4
Packaging: Cholic acid is sealed in a polyethylene liner and packed in 25kg fibre drums. Customer specific packaging can be provided.