3 AZAFRIN 285 



Solvent Absorption maxima 



Carbon disulphide 483 452 m^ 



Chloroform 472 440 m^ 



Petrol 454 429 m/z 



Azafrinone m.onoxim.e C27H37O4N: 

 CHo CHi 



\/ 



C CH3 GS3 CHo 



/\ I I I 



CH2 CO- CH=CH- C=CHCH=CH- C=CHCH=CHCH=C- CH=CH- COOH 



CH, C=NOH 



\ / \ Azafrinone monoxime 



CH2 CH3 



Like semi-j8-carotenone, azafrinone only forms a monoxime. It separates from 

 acetone in crystals, m.p. 194° (corr.)^^^. 



A zafrinone methyl ester CgsHjgO^ : 

 CHo CHo 



A r r r 



CH3 CO- CH=CH- C=CHCH=CH- C=CHCH=CHGH=C- CH=CH- COOH. 



I 



CH, CO-CH, 



Azafrinone methyl ester 

 CHa 



This compound is obtained by the esterification of azafrinone suspended in 

 ether with diazomethane^^^, or by the oxidation of azafrin methyl ester with 

 chromic acid^®'*. 



The ester crystallises from petrol in red needles, m.p. 112° (corr.). It is 

 sparingly soluble in hexane, somewhat more soluble in ethanol, ether and acetic 

 acid, and easily soluble in chloroform, acetone, benzene, and pyridine. The 

 chromatographic behaviour of azafrinone methyl ester is similar to that of 

 azafrin methyl ester. 



Solvent Absorption maxima 



Carbon disulphide 483 452 m^ 



Chloroform 472 440 va.fi 



Petrol 454 429 m/i 



Azafrinone amide C27H37O3N: 

 CH, CHo 



(of. Fig. 23, p. 357) 



C CHs CH3 CH3 



CH2 CO- CH=CH- C=CHCH=CH- C=CHCH=CHCH=C- CH=CH- CO- NH^ 



CHa CO-CHs 



Azafrinone amide 

 CH, 



References p. 2go-2g4. 



