Sorbic Acid as an Alkylating Agent |
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Authors: | M Teresa Pérez-Prior José A Manso M del Pilar García-Santos Emilio Calle Julio Casado |
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Institution: | (1) Departamento de Química Física, Universidad de Salamanca, Plaza de la Merced, 37008 Salamanca, Spain |
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Abstract: | A kinetic study of the alkylating potential of the sorbic acid + NaOH and sorbic acid + KOH systems was performed in 7:3 (volume/volume)
water + dioxane solvent mixtures. The following conclusions were drawn. First, the sorbic acid + sorbate system shows alkylating
activity on the nucleophile 4-(p-nitrobenzyl)pyridine (NBP), which is used as a trap for alkylating agents having nucleophilic characteristics similar to
DNA bases. Second, the maximum alkylating capacity is observed in the pH = 5.0 to 6.5 range. Third, the alkylation reactions
comply with the rate equation r=k
alkH+]S]NBP]/(K
a
+H+]), with K
a
being the dissociation constant of sorbic acid. Fourth, an enthalpy–entropy (ΔH
#/ΔS
#) compensation effect for activation quantities is observed by comparing NBP alkylation reactions due to sorbic acid + NaOH,
sorbic acid + KOH, as well as potassium sorbate + HCl mixtures. Fifth, the results may help to establish suitable expiration
times for products preserved with sorbic acid. |
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Keywords: | Sorbic acid Alkylating potential Food preservatives |
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