| IUPAC names
|3D model (Jmol)||Interactive image|
|Molar mass||392.57 g/mol|
|Melting point||165 to 167 °C (329 to 333 °F; 438 to 440 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|(what is ?)|
Chenodeoxycholic acid (also known as chenodesoxycholic acid, chenocholic acid and 3α,7α-dihydroxy-5β-cholan-24-oic acid) is a bile acid. It occurs as a white crystalline substance insoluble in water but soluble in alcohol and acetic acid, with melting point at 165-167 °C. Salts of this carboxylic acid are called chenodeoxycholates. Chenodeoxycholic acid is one of the main bile acids produced by the liver.
Chenodeoxycholic acid is synthesized in the liver from cholesterol by a process which involves several enzymatic steps. Like other bile acids, it can be conjugated in the liver with taurine or glycine, forming taurochenodeoxycholate or glycochenodeoxycholate. Conjugation results in a lower pKa. This means the conjugated bile acids are ionized at the usual pH in the intestine and will stay in the gastrointestinal tract until reaching the ileum where most will be reabsorbed. Bile acids form micelles which facilitate lipid digestion. After absorption, they are taken up by the liver and resecreted, so undergoing an enterohepatic circulation. Unabsorbed chenodeoxycholic acid can be metabolised by bacteria in the colon to form the secondary bile acid known as lithocholic acid.
Choendeoxycholic acid is the most potent natural bile acid at stimulating the nuclear bile acid receptor, farnesoid X receptor (FXR). The transcription of many genes is activated by FXR.
Chenodeoxycholic acid has been used as medical therapy to dissolve gallstones.
Chenodeoxycholic acid can be used in the treatment of cerebrotendineous xanthomatosis.
In supramolecular chemistry, molecular tweezers based on a chenodeoxycholic acid scaffold is a urea receptor that can contain anions in its binding pocket in order of affinity: H2PO4− (dihydrogen phosphate) > Cl− > Br− > I− reflecting their basicities (tetrabutylammonium counter ion).
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- Giaconda. "Press release". Retrieved 5 April 2014.
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- Rao AS, Wong BS, Camilleri M, et al. (November 2010). "Chenodeoxycholate in females with irritable bowel syndrome-constipation: a pharmacodynamic and pharmacogenetic analysis". Gastroenterology. 139 (5): 1549–58, 1558.e1. doi:10.1053/j.gastro.2010.07.052. PMC 3189402. PMID 20691689.
- Ki Soo Kim, Hong-Seok Kim Molecular Tweezer Based on Chenodeoxycholic Acid:Synthesis, Anion Binding Properties. Bulletin of the Korean Society 1411-1413 2004 Article Archived September 27, 2007, at the Wayback Machine.