714 VII. LIPID DISTRIBUTION IN SPECIFIC TISSUES 



has shown to be present in the liver oil of the basking shark (Cetorhinus 

 maximus) to the extent of 6 to 10%. A still more unsaturated hydrocarbon, 

 gadusene, Ci8H 32 , has been isolated from the liver of the Japanese ishinagi 

 (Stereolepis ishinagi). 61 Strangely enough, this latter compound is like- 

 wise present in the unsaponifiable fraction of soybean oil, rice germ oil, 62 

 wheat germ oil, 63 and in other fish liver oils. 62 For a more complete ex- 

 position of the chemistry and distribution of these lipids, the reader is 

 referred to Volume I, pages 400-404. 



(c) Glyceryl Ethers. The glyceryl ethers constitute very important com- 

 ponents in the liver lipids of certain fishes. The three members of this 

 group include : 



chimyl alcohol, CH 3 (CH 2 ) 14 CH 2 OCH 2 CHOHCH 2 OH, 



batyl alcohol, CH 3 (CH 2 ) 16 CH 2 OCH 2 CHOHCH 2 OH, 



selachyl alcohol, CH 3 (CH 2 ) 7 CH:CH(CH 2 ) 7 CH 2 OCH 2 CHOHCH 2 OH. 



They represent combinations of palmityl, stearyl, and oleyl alcohols, 

 respectively, with the a-hydroxyl of glycerol, to form water-insoluble ethers. 

 The glyceryl ethers were discovered by Tsujimoto and Toyama 64 in the 

 unsaponifiable fraction of the liver oil of such elasmobranch fishes as the 

 shark and ray. The glyceryl ethers may be present in a relatively high 

 concentration. Thus, practically all of the non-saponifiable fraction of 

 ratfish liver oil (Chimaera monstrosa), which constitutes 37% of the total 

 liver lipid, consists of selachyl alcohol. 65 However, the glyceryl ethers are 

 present not only in the elasmobranch family, but also in the Japanese 

 crab (Paralithoides camtschatica Tilesius). 66 In fact, batyl alcohol has been 

 isolated from the bone marrow of cattle, 67 from the spleen of pigs, 68 and from 

 the arteriosclerotic arteries of human beings, 69 although it has not been 

 detected in the liver lipids of the higher animals. For a more detailed 



61 M. Tsujimoto, Bull. Chem. Soc. Japan, 6, 237-239 (1931); Chem. Abst., 26, 612- 

 613 (1932). 



62 Z. Nakamiya, Sci. Papers Inst. Phys. Chem. Research (Tokyo), 28, 16-26 (1935). 



63 J. C. Drummond, E. Singer, and R. J. MacWalter, Biochem. J., 29, 457-471 (1935). 



64 M. Tsujimoto and Y. Toyama, Chem. Umschau Fette, Ole, Wachse, u. Harze, 29, 

 27-29, 35-37, 43-45 (1922); Y. Toyama, Ibid., 29, 237-240, 245-247 (1922); 31, 13-17, 

 61-67, 153-155 (1924). 



65 T. P. Hilditch, The Chemical Constitution of Natural Fats, Wiley, New York, 1947. 



66 M. Tsujimoto, /. Soc. Chem. Ind. Japan, 32, 362B-364B (1929); Chem. Abst., 24, 

 4650 (1930). 



67 H. N. Holmes, R. E. Corbet, W. B. Geiger, N. Kornblum, and W. Alexander, /. Am. 

 Chem. Soc, 63, 2607-2609 (1941). 



68 V. Prelog, L. Ruzicka, and P. Stein, Helv. Chim. Acta, 26, 2222-2242 (1942). 



69 E. Hardegger, L. Ruzicka, and E. Tagmann, Helv. Chim. Acta, 26, 2205-2221 

 (1943). 



