78 II. DIGESTION AND ADSORPTION OF FATS 



number of investigations, 454-457 it remains unsolved. However, Fieser and 

 Fieser 399 have postulated the structure shown by IX. Hammarsten 458 



OH CH 3 

 CH 3 



HO H 



(IX) Scymnol 



isolated what proved to be an unusual bile acid from the seals, Phoca 

 barbata, P. groenlandica (harp seal), P. foetida, and Cystophora cristata 

 (hooded or "bladder-nose" seal) and from the walrus (Odobaenus, spp.). 

 He called it "/3-phocaecholic" acid; it is believed to be 3,7,23-trihydroxy- 

 cholanic acid, 459 but the configuration of the hydroxyls is not known. 



Haslewood 460 reported that, in addition to the regular occurrence of 

 cholic acid in the Teleostei, chenodesoxycholic acid was present in many 

 species. A tetrahydroxy acid was reported in four different biles; in all 

 cases, the bile acids were conjugated with taurine. 460 Tukamoto and Ka- 

 taoka 437 found that the bile acids in two marine fishes, namely the goby 

 or haze (Acantfwgobius flavimanus) and the tobihaze or walking fish 

 (Periphthalmus canto nensis) consisted of cholic and chenodesoxycholic 

 acids. However, Ohta 461 and Isaka and Azato 462 reported a C 27 -acid having 

 the empirical formula of C07H46O6, which is 3, 6, 12, 24-tetrahydroxy- 

 norsterocholanic acid (formula X), in the bile of the "gigi" or bone-fish 

 (Pelteobagrus nudiceps, recte Pimelodus fulvidracus) , while Tsaka and Azato 462 

 isolated this acid from the "aigo" or tang (Siganus fuscescens Hauttyn) 

 and the "fugu" or globe-fish (Tetrodon porphyleus Sieb.). Strangely 

 enough, Yamasaki 463 recorded the presence of this same tetrahydroxy- 

 norsterocholanic acid in the bile of the hen. 



454 A. Windaus, W. Bergmann, and G. Konig, Z. physiol. Chem., 189, 148-154 (1930). 



466 R. Tschesche, Z. physiol. Chem., 203, 263-271 (1931). 



456 H. Asikari, J. Biochem. {Japan), 29, 319-324 (1939); Chem. Zentr., 110, II, 2666 

 (1939). 



467 W. Bergmann and W. T. Pac-e, J. Am. Chem. Soc, 65, 477-478 (1943). 



458 O. Hammarsten, Z. physiol. Chem,., 61, 454-494 (1909); 68, 109-118 (1910). 

 469 A. Windaus and A. van Schoor, Z. physiol. Chem., 173, 312-320 (1928). 



460 G. A. D. Haslewood, Biochem. J., 47, liv-lv (1950). 



461 K. Ohta, Z. physiol. Chem., 259, 53-61 (1939). 



462 H. Isaka and M. Azato, ./. Biochem. {Japan), 32, 241-247 (1940). 

 163 K. Yamasaki, /. Biochem. {Japan), 38, 93-98 (1951). 



