NATURAL WAXES 311 



tode {Ascaris megalocephala) and from the round worm {Ascaris lum})ri- 

 coides) ; this alcohol probably also contains some carbonyl groups, as it has 

 four oxygens (C3sH6804).^'' 



Another interesting ketonic alcohol which has been prepared from 

 cochineal wax {Coccus cacti) is 15-keto-n-tetratriacontanol, CH3(CH2)i8- 

 CO(CH2)i3CH20H, which melts at 100.5-100.7.^^ Becker^« reports the 

 preparation of cocceryl alcohol from the cochineal wax coccerin, which has 

 two less carbons than the ketonic alcohol, and which is diatomic. The 

 formula is given as C32Hg4(OH)2, and it has a melting point of 102°C. One 

 wonders whether these two products may be identical. Phthiocerol is a 

 dihydrox}'^ monomethoxj^ alcohol, C36H72O3, which has been found to be a 

 component of the wax of tubercle bacilli. Although it was first separated 

 from the human tubercle bacilli, ^^-^^ it has since been shown to be a com- 

 ponent of the bovine type. ^^ This alcohol is optically active, [«]„ = —4.8°, 

 and it melts at 73-74 °C. 



A list of some of the unsaturated alcohols which have been found as com- 

 ponents of waxes is given in Table 2. 



Octadecyl alcohol (or oleyl alcohol), CH3(CH2)7CH:CH(CH2)7CH20H, 

 is the most important member of the group of unsaturated alcohols. It is 

 found largely in fish oils. Tsujimoto*" and Toyama^^'^' first discovered it in 

 certain shark oils; they later found it in sperm oils,^^ including the oil 

 from the Arctic sperm whale. The blubber oil is composed of 66 to 70% of 

 oleyl alcohol, while the head oil contains 27 to 30% of this component.'*'- 

 Oleyl alcohol comprises 25% of spermaceti.^* About 30% of the head oil 

 of the porpoise also consists of octadecyl alcohol.^ 



In addition to oleyl alcohol, most of the other unsaturated alcohols are of 

 marine origin. Thus, Toyama and Tsuchiya,^* citing Tsujimoto,*" have 

 reported 5-tetradecenol (physeteryl) and 9-hexadecenol (zoomaryl alcohol) 

 in sperm head oil. Moreover, Toyama and Akiyama have demonstrated 

 that hexadecenol in sperm blubber oil is identical with zoomaryl alcohol 



34 F. N. Sfhulz and M. Becker, Biochem. Z., 265, 253-259 (1933). 



^ A, C. Chibnall. A. L. Latner, E. F. Williams, and A. Ayre, Biochem. J., 28, 313-325 

 (1934). 



38 M. Beciker, Biochem. Z., 239, 235-242 (1931). 



3^ F. H. Stodola and R. J. Anderson, ./. Biol. Chem., II4, 4G7-472 (193G). 



38 C. W. Wieghard and R. J. Anderson, /. Biol. Chem., 126, 515-526 (1938). 



33 J. Cason and R. J. Anderson, J. Biol. Chem., 126, 527-541 (1938). 



^» M. Tsujimoto, /. Soc. Chem. Ind. Japan, 24, 41-45 (1920); Chem. AbsL, 15, 2006 

 (1921). 



*i Y. Tovama, Chem. Umschaii Felte, Ole, Wachse Harze, 29, 237-240, 245-247 (1922); 

 Chem. AbsL, 17, 892-893 (1923). 



« T. P. Ililditch and J. A. Lovern, ./. Soc. Chem. Ind., 48, 359-364T (1929). 



« M. T. Francois, ./. pharm. chim., 12, 189-191 (1930). 



*^ Y. Toj'ama and T. Tsuchiya, Bull. Chem. Soc. Japan, 10, 563-569, 570-573, 573- 

 579(1935). 



