Chenodeoxycholic acid

From Wikipedia, the free encyclopedia

Chenodeoxycholic acid

Systematic name	chenodiol 3α,7α-dihydroxy-5β-cholanic acid 5β-cholanic acid-3α,7α-diol
Chemical formula	C₂₄H₄₀O₄
Molecular mass	xx.xx g/mol
Density	x.xxx g/cm³
Melting point	165-167 °C
Boiling point	xx.x °C
CAS number	[474-25-9]
SMILES	C[C@@]34[C@] (CC[C@@H]4[C@@H] (CCC(O)=O)C) ([H])[C@]2([H]) [C@H](O)C[C@]1 ([H])C[C@H](O) CC[C@@](C)1 [C@]([H])2CC3
Disclaimer and references

Chenodeoxycholic acid is a bile acid, a white crystalline substance insoluble in water, with melting point at 165-167 °C. Its salts is called chenodeoxycholates. Chenodeoxycholic acid is one of the 4 main organic acids produced by the liver. It is soluble in alcohol and acetic acid.

Chenodeoxycholic acid is synthetized in the liver from cholesterol.

This compound, when altered by bacteria in the colon, will result in conversion to its secondary bile acid known as lithocholic acid. Both of these bile acids, in addition to the others, can be conjugated to taurine or glycine. Conjugation, a function carried out by the liver will result in a lowered pKa and therefore, the compounds will remain ionized. These ionized compounds will stay in the gastrointestinal tract until reaching the ileum where they will be reabsorbed. The purpose of this conjugation is to keep the bile acids in the tract until the end to facilitate lipid digestion all the way to the ileum.

In cases where bacteria overgrow in the small intestine, often due to a blind loop in the intestine retaining chyme in one place, the bacteria will de-conjugate the bile acids and therefore impede fat digestion and absorption. This can lead to steatorrhea.

Chenodeoxycholic acid and cholic acid are the most important human bile acids. Some other mammals synthetize predominantly deoxycholic acid.

The Australian biotechnology company Giaconda has developed a treatment for Hepatitis C infection that combines chenodeoxycholic acid with bezafibrate.