1887

Abstract

Summary: Studies of the -oxidation of the fatty acid side-chain of certain -aryl- and -aryloxy--alkylcarboxylic acids by (strain T) and sp. (strain P) show that y-phenylbutyric is more rapidly oxidized than y-phenoxy- butyric acid. The effect of the oxygen bridge is even more striking when -(1-naphthyl)- and -(1-naphthyloxy)-butyric acids are compared. The rate of -oxidation (by strain T) of 3-, 4-, and 2-isomers decreases in that order. This applies to mono-chloro- and monomethylphenoxybutyric acids and to monochlorophenoxypropionic acids. Substitution in position 2 has by far the greatest effect and chlorine exerts a bigger influence than a methyl group in all positions. The conversion of -(2-methyl- 4-chlorophenoxy)-butyric acid (MCPB) and -(2:4-dichlorophenoxy)-butyric acid (2:4-DB) is very slow and proceeds only to -hydroxy acids. On the other hand, -(2-methyl-4-chlorophenoxy)-, -(2:4-dichlorophenoxy)- and -(2-chlorophenoxy)-caproic acids are relatively rapidly converted to their corresponding butyric acid derivatives. With strain T -(2-naphthyloxy)-butyric and propionic acids are more rapidly converted to their corresponding acetic acids and phenols respectively than the -(1-naphthyloxy) compounds. The rate of -oxidation of -phenyl-, -(3-indolyl)- and -(1-naphthyl)- butyric acids (by strain P) decreases in that order. It has been shown that -hydroxy acid intermediates are formed from -aryloxybutyric acids and those from MCPB, -(2-methyl-4-chlorophenoxy)-crotonic and -(2-naphthyl-oxy)-butyric acids have been isolated and identified.

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/content/journal/micro/10.1099/00221287-18-3-733
1958-06-01
2021-10-25
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