Tabulation of Known Acids and Alcohols

This acid, the parent compound of the hydroxylated C24 5 acids, was detected as a trace component of human feces by Ali et al. in 1966 (50). It has not been detected elsewhere as a naturally occurring substance. Preparations of cholanic acid have been obtained by Clemmenson or Wolff-Kishner reduction of fully oxidized bile acids or by pyrolysis of hydroxy acids followed by hydrogenation of the resulting mixture (1). 

Lithocholic acid was first isolated from a gallstone by Fischer in 1911 (30). It was later isolated from ox bile (1 g from 100 kg of bile) (64) from rabbit bile (0.4 g from 900 ml) (65) and subsequently from monkey, human, pig, and guinea pig bile (2, 66, 67). Lithocholic acid has been identified as one of the bile acids in human blood (68) and as a principal fecal bile acid. Moset-tig et al. (69) isolated lithocholic acid from human stool and estimated its concentration to be 3 g/100 kg of fresh stool. Lithocholic acid is particularly insoluble, is not hydroxylated to an appreciable extent in man (70), and may be the cause of liver disease (4). In early studies lithocholic acid was not available in sufficient amounts from natural sources and was prepared from cholic acid. Lithocholic acid was particularly valuable in establishing the correspondence of the B/C ring structure between bile acids and cholesterol (71). 

This acid, the 3/3-epimer of lithocholic acid, has been detected as a component of the feces of man and rabbit (32, 62, 73, 74). A compound named isolithocholic acid was isolated from chicken bile in an early study by Hosizima et al. (15). However, the properties of this acid do not coincide with those of 3/3-hydroxycholanic acid. The 3 acid has been prepared from the ketone by hydrogenation under acidic conditions (72). 

This acid was detected by Ali et al. (50) as a trace component of human stool. It has not been detected elsewhere in nature. 7/3-Hydroxycholanic acid may be prepared by reduction of the 7-keto acid with sodium and propanol (76). 

Wieland (32) and Windaus (33) independently discovered chenodeoxycholic acid in different biles (man and goose) in 1924. The same acid had been detected previously in goose bile in 1848 by Marsson (22), who named 

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A thorough review of the chemistry of many of the naturally occurring bile acids and related substances may be found in the monograph by Fieser and Fieser (1). A tabulation of known acids and alcohols, their properties, and a brief description of their origins is presented in the next section of this chapter. Identifications in some cases have not been confirmed but the burden of accuracy has been left with the original authors. 

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