392 



IV. WAXES, HIGHER ALCOHOLS, ETC. 



Lupeol 



3. Glyceryl Ethers 



The glyceryl ethers consist of the three alcohols: batyl, chimyl, and 

 selachyl. In these compounds, the component aliphatic alcohol (palmityl, 

 stearyl, or oleyl) is combined with glycerol at the a-position in an ether 

 linkage which forms a stable non-hydrolyzable union. Selachyl alcohol is 

 found most abundantly in natiu'e, while chimyl alcohol appears least fre- 

 quently and in the smallest amount. Selachj'l alcohol is the ether of 

 oleyl alcohol and glycerol, while batjd alcohol can only be the correspond- 

 ing stearyl ether, since it originates upon the hydrogenation of selachyl 

 alcohol. 



CHj(CH2)tCH:CH(CHj)7CH20CHj CHOH CH2OH 

 Selachyl alcohol 



CHj(CH2)i6CH20 CHzCHOH CH20H 

 Bat\l alcohol 



Chimyl alcohol, CH3(CHo)i4CH2 0CH2CHOHCH20H, is the lower 

 homologue of batyl alcohol in which cetyl (palmityl) alcohol replaces the 

 stearjd alcohol. Like the corresponding oleyl alcohol and triolein, selachyl 

 alcohol is liquid at room temperature. Also in line with the melting points 

 of cetyl and stearjd alcohols (as well as of tripalmitin and tristearin), 

 chimyl and batyl alcohols have relativel}'^ high melting points (60-61. 5°C. 

 and 70-71 °C., respect iveh'.-^^^ 



^^ T. P. Hilditch, in H. Schonfeld, Chemie und Technologie der Felte inid Fettprodukie, 

 Vol. T, Springer, Vienna, 19.36, pp. 60-110. 



