Anticlostridial Agents

1. Field of the Invention

This invention relates to mono-, di-, and mixed-n-alkyl maleates and fumarates as food preservatives, and more particularly, to the extraordinary anticlostridial activity exhibited by some selected long chain esters.

2. Description of the Art

The methyl, ethyl and propyl dialkyl esters of fumaric acids have been shown to possess antimicrobial activity and methyl and ethyl fumarates were found to exhibit some antibotulinal activity.

An object of this invention is to provide novel compounds that are potent inhibitors of the growth of Clostridium botulinum.

Another object is to provide a method of preventing spoilage in food and other products.

A further object is to provide a method of treating foods so they can be stored safely for extended periods of time.

According to this invention, the above objects are accomplished by a number of mono-, di-, and mixed n-alkyl maleates and fumarates and their use as inhibitors of the growth of Clostridium botulinum. The objects are especially accomplished by the monoalkylesters of maleic and fumaric acids in which the alkyl group of each ester is selected from those alkyl groups containing from 13 to 18 carbon atoms, and by the incorporation of one or more of these esters in foodstuffs in a Clostridium botulinum inhibiting effective amount.

A number of n-alkyl esters of maleic and fumaric acids were found to exhibit some anticlostridial activity. However, the minimum inhibitory concentration (MIC) of these esters is, in many cases, 1.5 to 2.0 times that of sodium nitrite. Although the amounts of these compounds required to protect food products from the deleterious effects of Clostridium botulinum may be considered high, the compounds have the advantage of being essentially nontoxic and useable in place of sodium nitrite and ethylene dibromide which are known to have carcinogenic properties.

The main focus of our invention is our discovery that certain esters of maleic and fumaric acids are very potent inhibitors of the growth of Clostridium botulinum. In fact, some of them are 1000 times more active, that is, their MIC is 1000 times less, than sodium nitrite.

As shown in the table, the n-monoalkylmaleates and n-monoalkylfumarates in which the ester moiety has a 13 to 18 carbon atom chain length are very potent inhibitors of the growth of Clostridium botulinum. The MIC for these compounds ranges from 0.2 to 3.1 .mu.g/ml. The n-dialkylfumarates and the n-methylalkylfumarates which have ester moieties in the same chain length range as those of the monoalkyl compounds are generally more potent than sodium nitrite in anticlostridial activity, but they are not comparable in activity to the highly potent monoalkylmaleates and fumarates.

Since the compounds of this invention do not present a problem with regard to toxicity and have extremely low MIC values, they are excellent compositions to use in place of sodium nitrite and ethylene dibromide in the preservation of a variety of foodstuffs.