Description and references

A major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus facilitates its excretion. Facilitates fat absorption in the small intestine by micellar solubilization of fatty acids and monoglycerides. Has cathartic properties since it induces fluid secretion from large intestine. Main constituent of the bile of hens, geese and other fowl; occurs in appreciable amounts in the bile of hamster, hog, guinea pig, bear and man. Epimeric with ursodiol, q.v. Isoln: Windhaus et al., Z. Physiol. Chem. 140, 177 (1924); Wieland, Reveney, ibid. 186. Configuration: Lettré, Ber. 68, 766 (1935). Prepn from cholic acid: Fieser, Rajagopalan, J. Am. Chem. Soc. 72, 5530 (1950); Hauser et al., Helv. Chim. Acta 43, 1595 (1960); Hofmann, Acta Chem. Scand. 17, 173 (1963). Alternate prepns: Sato, Ikekawa, J. Org. Chem. 24, 1367 (1959); T. Iida, F. C. Chang, ibid. 46, 2786 (1981). Stereoselective total synthesis: T. Kametani et al., J. Am. Chem. Soc. 103, 2890 (1981). Asymmetric total synthesis of (+)-form: eidem, J. Org. Chem. 47, 2331 (1982). Dissolution of cholesterol gallstones: Danzinger et al., N. Engl. J. Med. 286, 1 (1972); Bell et al., Lancet II, 1213 (1972). Use in long-term treatment of cerebrotendinous xanthomatosis: V. M. Berginer et al., N. Engl. J. Med. 311, 1649 (1984). Monograph on bile acids: The Bile Acids, 2 vols., P. P. Nair, D. Kritchevsky, Eds. (Plenum Press, New York, 1971, 1973). Review of pharmacology and therapeutic use of chenodeoxycholic acid: J. H. Iser, A. Sali, Drugs 21, 90-119 (1981). Effect on cholesterol and bile acid metabolism: G. S. Tint et al., Gastroenterology 91, 1007 (1986).

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