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Long chain carboxylic acids containing ether linkage: IV. The antibacterial activities of 0‐(2‐alkylaminoethyl)‐3‐oxypropionic and N‐(2‐alkyloxyethyl)‐3‐aminopropionic acids
Author(s) -
Abe Yoshiro,
Osanai Shuichi,
Matsumura Shuichi
Publication year - 1972
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02633389
Subject(s) - ether , antibacterial activity , chemistry , amine gas treating , aqueous solution , amino acid , carboxylic acid , escherichia coli , organic chemistry , medicinal chemistry , stereochemistry , bacteria , biochemistry , biology , genetics , gene
The carboxylic amphoteric surfactants containing ether and substituted amine groups such as 0‐(2‐alkylaminoethyl)‐3‐oxypropionic‐and N‐(2‐alkyloxyethyl)‐3‐aminopropionic acids were synthesized, and their antibacterial activities in terms of growth inhibition of Staphylococcus aureus and Escherichia coli were examined. The structural effect, such as bonding position of ether and amino groups, and the chain length effect between undecyloxy‐, dodecyloxy‐ and tridecyloxy radicals were examined, but no definite correlation between positional isomers and chain length and antibacterial activities was observed. Furthermore, to study the effect of the increase of the number of ether or amino groups on the antibacterial activities, N‐(2‐(2‐dodecyloxyethyl)‐aminoethyl)‐3‐aminopropionic acid and N‐(2‐(2‐dodecyloxyethyl)oxyethyl)‐3‐aminopropionic acid were synthesized. Their antibacterial activities were almost as effective as the corresponding amino or ether acids. Moreover aqueous solution of these substituted propionic acids showed better surface activities at pH 4.0, 7.0 and 10.0.