Inhibition of Clostridium botulinum 62A by fumarates and maleates and relationship of activity to some physicochemical constants

Abstract

A series of n-monoalkyl maleates and n-mono-, di-, and methyl n-alkyl fumarates were prepared, 18 esters of each, with R = CH3 to C18H37. Their activity against Clostridium botulinum was determined in culture medium. The n-monoalkyl maleates and fumarates possessed significant activity, particularly those esterified with higher C13 to C18 alcohols. Somewhat lower activity was exhibited by methyl n-alkyl fumarates, while symmetrical esters, di-n-alkyl fumarates, were almost inactive. An attempt was made to correlate the activity of n-monoalkyl maleates and fumarates with chain length, solubility in water, apparent dissociation constant (pKa'), and infrared and UV absorption frequencies. The active esters may have potential as preservatives in foods.