3 AZAFRIN 287 



purification, the reaction mixture is chromatographed on alumina from benzene 

 solution. The derivative crystallises from dilute methanol in dark red leaflets 

 with a violet lustre. M.p. 149-150°. 



Solvent Absorption maxima 



Petrol 476 447 420 m/^ 



Anhydroazafrinone amide C2-jii2b^2^-^^^ 



The preparation of anhydroazafrinone amide from /3-carotene or azafrinone 

 has already been described (pp. 134 and 283). The amide crystallises from 

 methanol in red-violet needles, m.p. 215°. It is sparingly soluble in hexane, 

 petroleum ether and petrol, but somewhat more easily soluble in chloroform 

 and hot benzene. 



Solvent Absorption maxima 



Carbon disulphide 508 474 444 vn.(x 



Hexane 475 444 419 m^ 



Petroleum ether 473 443 418 m/^ 



Benzene 477 447 420 vafi 



Chloroform 492 459 430 mn 



Ethanol (481) (450) mjx 



Perhydroazafri?i C27H52O4 : 



Perhydroazafrin can be obtained either by the catalytic hydrogenation of 

 azafrin^^^ or by the saponification of perhydroazafrin methyl ester^^". It is a 

 colourless, viscous oil which can be distilled in high vacuum. 



Optical rotation in ethanol.- [a]^ = —6.7° (c = 3.2)169. 



Apo-i-azafrinal CgjHjgOg: 



\/ 



C OH CH, CH, CH, 



/\/ I I I 



CHg C- CH=CH- C=CHCH=CH- C=CHCH=CHCH=C- CHO 



I I 



CHo C'CHj 



^ Apo-i-azafrinal 



CHj OH 



This aldehyde was obtained by Karrer, Obst and Solmssen"^ by the 

 careful permanganate oxidation of azafrin. It crystallises from benzene in 

 orange-yellow needles, m.p. 17.1°. 



Solvent Absorption maxima 



Carbon disulphide 461 m/z 



Petroleum ether 431 m// 



Ethanol diffuse 



References p. 2go-2g4. 



