402 IV. WAXES, HIGHER ALCOHOLS, ETC. 



which decomposes on treatment with water to carbon dioxide, formalde- 

 hyde, acetone, succinic, and levulinic acids, and, in addition, to two unde- 

 fined acids with the formulas CeHwOs and CsHuOe."^^'^^" On dry distillation 

 of squalene, isoprene and cyclodihydromyricin are formed; this is taken to 

 indicate that it is a dihydroterpene. Heilbron et al^^^ were also able to 

 separate a series of hemiterpenes, monoterpenes, sesquiteipenes, and 

 diterpenes by the distillation of squalene. These reactions would all seem 

 to offer justification for defining this hydrocarbon as a class of triterpenes 

 which is non-cyclized. 



(2) Pristane 



Pristane, CisHsg, is another hydrocarbon which has been separated by 

 Tsujimoto'"*'^" from the liver oil of the basking shark, where it was 

 present to the extent of 6-10%. According to Toyama,^^- pristane is 

 present in most liver oils which contain squalene, but only in small amounts. 

 Toyama and Tsuchiya^^^ have found it also in sardine, herring, sperm whale, 

 and other oils. It is presumably a branched-chain, saturated hydrocarbon, 

 but the structure is unknown. It is a colorless liquid which boils at 296 °C. 



(3) Other Hydrocarbons 



Gadusene, CisHsa, has been isolated from wheat germ oil by Drummond 

 et aL,^** which is probably the same as the material separated earlier by 

 Tsujimoto^*^ from the liver oil of the Japanese ishinagi (Stereolepis 

 ishinagi) . Nakamiya**® isolated gadusene from the unsaponifiable fraction 

 of rice germ oil, soybean oil, and some fish liver oils. It had the same ab- 

 sorption spectrum as the samples that Tsujimoto^^^ and Drummond et aZ.^*^ 

 had prepared from other sources; thus, it is apparently identical with 

 them. Oleastane, C21H36, has been isolated from the fruit of the olive,*" 

 while another octadecylene called zamene, CisHse, has been prepared from 

 the liver oil of the basking shark.^^s Marcelet**^ reported that the non- 

 saponifiable fraction of peanut oil contains hypogene, C15H30, and arachi- 

 dene, C19H38. The following hydrocarbons were identified from olive oils: 



"9B. Kubota, J. Chem. Soc. Tokyo, 39, 879-907 (1918); Chem. AbsL, 13, 441 (1919). 



^« R. Majima and B. Kubota, Japanese J. Chem., 1, 19-33 (1922). 



4" M. Tsujimoto, Ind. Eng. Chem., 9, 1098-1099 (1917). 



^^2 Y. Tovama, Chem. Umschau Fette, Die, Wachse Harze, 30, 181-187 (1923); Chein. 

 AbsL, 17, 3616 (1923). 



^" Y. Toyama and T. Tsuchiya, J. Soc. Chem. Ind. Japan, 38, suppl., 254-258 (1935). 



'^^ J. C. Drummond, E. Singer, and R. J. Mac Walter, Biochem. J., 29, 456-471 (1935). 



*« M. Tsujimoto, Btdl. Chem. Soc. Japan, 6, 237-239 (1931); Chem. Abst., 26, 612-613 

 (1932). 



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



<« G. Sani, Alti accad. Lincei, 12, 238-242 (1930). 



^^8 H. Marcelet, Bnll. soc. chim. [5], 3, 1156-1160, 2055-2057 (1936); Compt. rend., 

 202, 867-869, 1809-1811 (1936). 



