308 IV. WAXES, HIGHER ALCOHOLS, ETC. 



n-Octanol, n-decanol, and n-dodecanol have been found in traces in the 

 bhibber oil of the sperm whale (Physeter macrocephalus) ^ Gill and 

 Tucker^ noted the presence of both C12 and Ch alcohols in the head oil of 

 the porpoise {Phocaena communis), although Lovern^ failed to confirm this 

 observation. Dodecanol is the lowest alcohol to be reported as a com- 

 ponent of a vegetable wax; this has been found in the cuticle wax of the 

 cascara sagrada {Rhamnus 'purshiana)? n-Tetradecanol occurs to the 

 extent of about 8% in the wax esters of the head oil of the sperm whale^-* 

 and porpoise.^ 



Cetyl alcohol, or n-hexadecanol, was observed as early as 1817 by 

 ChevreuP" in sperm head oil,^ where it comprises about 45% of the total 

 alcohols.^ This compound has been reported, also, as a component of 

 Arctic sperm blubber oil,^^-^^ as well as of porpoise head oil.*' Cetyl alcohol 

 is present to the extent of 25% in the total alcohols of sperm blubber oil." 

 The wax found in the skulls of whales and dolphins is frequently referred 

 to as "spermaceti." 



Octadecanol is likewise a component of the so-called "spermaceti." It is 

 known to be present in small amounts in sperm head^'" and blubber oils,"'^'- 

 as well as in porpoise and dolphin blubber oils.*' In most cases it does not 

 exceed 5% of the total alcohols present. n-Eicosanol has been found as a 

 component of dermoid cysts. ^^ It may also occur in some of the preceding 

 sources in amounts too small to be identified. This C20 alcohol has been 

 reported in the seed oil of the Simmmidsia chinensis {californica) or goat- 

 nut (jojoba) in the amount of 14.6%, and the next higher homologue {n- 

 docosanol) to the extent of 33.7%. ^ Carnaubyl alcohol, C24H49OH, occurs 

 in wool fat,'' alkanet root wax {Anchusa tincioria) ,^^ and in the felted beech 

 coccus {Cryptococcus jagi) }^ 



Although there is some doubt as to whether ceryl alcohol (hexacosanol), 

 as frequently separated, is a single substance or rather a mixture of several 

 homologues, there seems to be some proof that it is distributed widely. 



4 S. Ueno and R. Kovama, Bull. Chem. Soc. Japan, 11, 39-1-403 (1936). 



6 A. H. Gill and C. M. Tucker, Oil & Fat Industries, 7, 101-102 (1930). 



6 J. A. Lovern, Biochem. J., 28, 394-402 (1934). 



^ R. A. Gortner, Outlines of Biochemistry, 3rd ed., Wiley, New York, 1949, p. 790. 



8 E. Andre and M. T. Francois, Compt. rend., 183, 663-665 (1926). 



9 T. P. Hilditch and J. A. Lovern, J. Soc. Chem. Ind., 48, 365-368T (1929). 

 i» M. E. Chevreul, Ann. chim. phys. [2], 7, 155-181 (1817). 



11 M. Tsujimoto, Chem. Umschau Felte, Ole, Wachse Harze, 32, 127-128 (1925); Chem. 

 AbsL, 19, 2882 (1925). 



12 Y. Tovama, J. Soc. Chem. Ind. Japan, 30, .527-532 (1927); Chem. Abst., 21, 4079, 

 (1927). 



13 F. Ameseder, Z. physiol. Chem., 52, 121-128 (1907). 



14 M. V. Betrabet and G. C. Chakravorti, ./. Indian Inst. Sci., AW, 41-51, 52-53 

 (1933). 



16 B. K. Blount, /. Chem. Soc, 1935, 391-393. 



