Chenodesoxycholic acid

The 13C NMR spectra of lithocholic acid, chenodesoxycholic acid, desocycholic acid and cholic acid have been analyzed and are discussed in the literature [570]. 

Medicinal agents (such as contraceptives) may result in proliferations of the intima in the hepatic artery and its branches. In some cases, these arterial alterations were associated with thrombosis in the hepatic veins. Phar-macons can trigger three different forms of damage to the sinusoids (7.) dilation of the sinusoids (e.g. by contraceptives), (2.) perisinusoidal fibrosis (e.g. by azathio-prine, vitamin A and cytostatic agents), and (i.) peliosis hepatis (e. g. by contraceptives, anabolic and androgenic steroids, azathioprine, chenodesoxycholic acid). (13, 28, 130) (s. p. 398) (s. fig. 21.8)... 

Prepn from coprostane, cholic acid, lithocholic acid, desoxy-and chenodesoxycholic acid Wieland, Weil, Z. Physio/. 

Most often Pj values are 3 to 5 decades smaller than the corresponding values the differences can be larger, e.g. for salicylic acid (19) which contains two acidic groups (Figure 25) [463], but also much smaller, e.g. for chenodesoxycholic acid, which forms micelles [462], or in the presence of lipophilic counter ions, e.g. for salicylic acid in the presence of tetrabutyl-ammonium bromide (20) (Figure 26) [463]. Lipophilicity and polarizability of the counterion have a significant influence on the partitioning of ion pairs e.g. [465 — 468]). 

The dehydration of desoxycholic acid (33) yielded a diene mixture that could be hydrogenated to cholanic acid (34). Wieland and his co-workers also showed that both lithocholic and chenodesoxycholic acids were related to cholanic acid (35, 36). The positions and configurations of the hydroxyl groups were determined in the course of a series of oxidative cleavage studies, which actually bore upon the question of the ring structure. 

Fig. 5. Cholic acid (III) Chenodesoxycholic acid (VII) desoxycholic acid (VIII) hyodesoxycholic acid (IX) lithocholic acid (X).

In mammalian liver parenchyma cells, the synthesis of the steroid skeleton which was described on p. 236 is extended by acquisition of an enzyme system leading to the production of the substances known as bile acids. In man, this s3mthesis yields cholic acid, desoxycholic acid and chenodesoxycholic acid. The hepatic parenchyma in mammals also conjugates these bile acids with taurine and with glycine. 

Bergstrom, S., and J. Sjovall Occurrence and metabolism of chenodesoxycholic acid in the rat. Bile acids and steroids 13. Acta chem. Scand. 8, 611 (1954). 

Some of the more abundant transformation products of cholesterol include the group of substances known as the bile acids. The acids which predominate in the bile of man are cholic acid (XVIII), desoxycholic acid (XIX), chenodesoxycholic acid (XX), and lithochoUc acid (XXI). 

Cholic (III) and chenodesoxycholic (VII) acids (Fig. 5), two of the common primary bile acids, undergo further chemical alterations by the action of microbial flora in the gut to give rise to several secondary bile acids (also possessing 24 carbon atoms), such as desoxycholic (VIII), hyodesoxy-cholic (IX), and lithocholic (X) acids (Fig. 5). 

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