|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.
It was first isolated from the bile of the domestic goose, which gives it the "cheno" portion of its name (Greek: χήν = goose).
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.
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).
- Russell DW (2003). "The enzymes, regulation, and genetics of bile acid synthesis". Annu. Rev. Biochem. 72: 137–74. doi:10.1146/annurev.biochem.72.121801.161712. PMID 12543708.
- Carey MC (December 1975). "Editorial: Cheno and urso: what the goose and the bear have in common". N. Engl. J. Med. 293 (24): 1255–7. doi:10.1056/NEJM197512112932412. PMID 1186807.
- Parks DJ, Blanchard SG, Bledsoe RK, et al. (May 1999). "Bile acids: natural ligands for an orphan nuclear receptor". Science. 284 (5418): 1365–8. doi:10.1126/science.284.5418.1365. PMID 10334993.
- Thistle JL, Hofmann AF (September 1973). "Efficacy and specificity of chenodeoxycholic acid therapy for dissolving gallstones". N. Engl. J. Med. 289 (13): 655–9. doi:10.1056/NEJM197309272891303. PMID 4580472.
- Berginer VM, Salen G, Shefer S (December 1984). "Long-term treatment of cerebrotendinous xanthomatosis with chenodeoxycholic acid". N. Engl. J. Med. 311 (26): 1649–52. doi:10.1056/NEJM198412273112601. PMID 6504105.
- Giaconda. "Press release". Retrieved 5 April 2014.
- Bazzoli F, Malavolti M, Petronelli A, Barbara L, Roda E (1983). "Treatment of constipation with chenodeoxycholic acid". J. Int. Med. Res. 11 (2): 120–3. PMID 6852359.
- 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 . 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.