Alkylating Potential of Potassium Sorbate

Pérez‐Prior, María Teresa; Manso, José A.; García-Santos, M. Pilar; Calle, Emilio; Casado, Julio

doi:10.1021/jf052152p

Cited by 29 publications

(30 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The values of k alk at different temperatures are shown in Table 2. Table 3 shows the activation parameters for NBP alkylation in the sorbate + NaOH and sorbate + KOH systems, as well as previous the results obtained in a hydrochloric acid medium [19]. Figure 4 depicts the good fit of the results by the Eyring equation [23]: The results obtained for the alkylation of NBP by sorbic acid + NaOH and sorbic acid + KOH, as well as by potassium sorbate + HCl, show that the activation parameters fluctuate over a wide range of values.…”

Section: Kinetics Of the Alkylation Reactionmentioning

confidence: 89%

“…In our previous work the alkylating potential of potassium sorbate in aqueous hydrochloric acid conditions was studied [19]. In the present study, the alkylation of NBP by sorbic acid + KOH and sorbic acid + NaOH mixtures was investigated and the results are compared.…”

Section: Introductionmentioning

confidence: 93%

“…Because (i) the reactivity of sorbate increases with decreasing pH, and (ii) the antimicrobial activity of the organic acids and their salts is mainly attributed to the inhibiting action of the undissociated acid molecule [2,21,22], in a previous work the reaction mechanism shown in Scheme 3 was proposed by us [19], where K a is the sorbic acid dissociation constant and k alk is the NBP alkylation rate constant for the undissociated acid.…”

Section: Kinetics Of the Alkylation Reactionmentioning

confidence: 99%

See 2 more Smart Citations

Sorbic Acid as an Alkylating Agent

et al. 2008

Self Cite

View full text Add to dashboard Cite

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, with K a being the dissociation constant of sorbic acid. Fourth, an enthalpy-entropy ( H # / S # ) 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.

show abstract

Section: Kinetics Of the Alkylation Reactionmentioning

confidence: 89%

Section: Introductionmentioning

confidence: 93%

Section: Kinetics Of the Alkylation Reactionmentioning

confidence: 99%

See 1 more Smart Citation

Sorbic Acid as an Alkylating Agent

et al. 2008

Self Cite

View full text Add to dashboard Cite

show abstract

“…However, some studies have shown that SA and its salts exhibit a weak genotoxic potential, [2][3][4] including causing damage to DNA 5) and having an alkylating activity on nucleophilic 4-(p-nitrobenzyl) pyridine. 6) Also, Soschin and Leyden reported that SA induced erythema and edema in human skin, 7) although the mechanism was not clarified.…”

mentioning

confidence: 99%

Negative and Positive Ion Mode LC/MS/MS for Simple, Sensitive Analysis of Sorbic Acid

Horiyama

Honda

Suwa

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Sorbic acid (SA: CH 3 -CH‫؍‬ ‫؍‬CH-CH‫؍‬ ‫؍‬CH-COOH) is one of the widely used food preservatives, although there have been some reports of its toxic activity, for example, on DNA and skin cells. In order to examine the effects of SA on mammalian tissues, we have developed a highly sensitive analytical method using LC/MS/MS with positive and negative ion mode electrospray ionization (ESI). In a previous study, we found that a nonacidic eluent offers better ionization efficiency than acids or their ammoniun salts. However, optimal results could not be obtained because the anion form of SA is poorly retained on a conventional reversed phase column. To resolve this problem, we chose a new type of column and used high-resolution mass spectrometry and positive ion mode analysis. There have only been a few reports using these methods in the positive mode, for example derivatized SA, because acid compounds such as SA are usually used in the negative ion mode. However, a new type of lowcarbon-content and polar-endcapped C18 phase column was developed for better separation of SA from the matrix. High-resolution selected reaction monitoring (SRM) gave the best signal to noise ratio in normal-resolution SRM. In the positive ion mode, the CH 3 OH-0.05% HCOOH/0.1% CH 3 COOH eluent system yielded the best ionization efficiency. We propose a highly sensitive and simple analysis using a two-ion-mode ESI SRM method. Such systems should allow quantification of the amount of SA in or around the cells, without the need for pretreatment such as solid phase extraction.

show abstract

“…On the other hand, previous reports have shown that SA and its salts exhibit a weak genotoxic potential [3][4][5] including damage to DNA 6) and alkylating activity on nucleophile 4-(p-nitorobenzyl) pyridine (NBP). 7) Also, Soschin and Leyden reported that SA induced erythema and edema of human skin, 8) but the mechanism was not clarified.…”

mentioning

confidence: 99%