316 



VII. ACIDS, AMIDES, ALDEHYDES AND HYDROCARBONS 



The oxidation of the amide is interfered with by the methyl group on 

 the /?-carbon atom; the body in this emergency reverts to w-oxidation. 



Another instance in which an inhibition of oxidation has been noted 

 through amide formation is in the case of the polyene acid amide. Kuhn, 

 Kohler, and Kohler^^ observed that jS-oxidation was inhibited, and co- 

 oxidation was strongly augmented in rabbits, mider such conditions, with 

 the resultant formation of polyene-w,w'-dicarboxylic acid amides. Thus, 

 the amide of octatrienoic acid gave rise to a dicarboxylic acid to the extent 

 of 42%, as follows: 



CH3CH;CHCH:CH-CH:CHCONH2 > 



2,4,6-Octatrienoic acid amide 



H00CCH:CH-CH:CHCH:CH-C0NH2 



Hexatriene('2,4,6)-dicarboxylic 

 acid (1,6) amide (1) 



The Inhibition of Complete Oxidation of Fatty Acid Amides in Polyene Acids 



Table 1 



The Extent of Absorption of Fatty Acid Amides 



AND THE Quantity Excreted as Dicarboxylic Acids by Dogs" 



n-Decanoic acid-A^-methyl- 



amide 67-68 



n-Dodecanoic acid-A'^-methyl- 



amide 57-58 



2-Methylnonanoic acid amide 75 . 5-76 

 4-Methyldodecanoic acid 



amide 75 . 0-76 



2-Methyltridecanoic acid 



amide 94.0-95 



5-Methyltetradecanoic acid 



amide 61.5-62 



35.0 



9.5 



140 



" Adapted from G. Weitzel, H. Schon, and H. Kalbe, Z. physiol Chem., 295, 173-187 

 (1953),pp. 176, 178. 



In an extended study of the metaboUsm of various straight-chain and 

 methyl-substituted acid amides, Weitzel, Schon, and Kalbe ^"'^ reported 



10^ G. Weitzel, H. Schon, and H. Kalbe, Z. physiol. Chem., 296, 173-187 (1953). 



