Sorbic Acid as an Alkylating Agent

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

doi:10.1007/s10953-008-9251-9

Cited by 18 publications

(17 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In previous work we studied the in vitro reactivity of several alkylating compounds capable of forming DNA adducts: sorbic acid [4] and sorbates [5], nitrosoureas [6,7], p-nitrostyrene oxide [8], and lactones [9][10][11][12]. The results revealed a correlation between the carcinogenicity of the substances and their reactivity with 4-(p-nitrobenzyl)pyridine (NBP), a trap for alkylating agents with nucleophilicity similar to that of DNA [13,14].…”

Section: Introductionmentioning

confidence: 99%

The reactivity of vinyl compounds as alkylating agents

et al. 2012

Self Cite

View full text Add to dashboard Cite

The reactions of 4-(p-nitrobenzyl)pyridine (a trap for alkylating agents with nucleophilicity similar to that of DNA) with the vinyl compounds acrylonitrile, acrylamide, acrylic acid, and acrolein, which can act as alkylating agents of DNA, were investigated. The following conclusions were drawn: (1) vinyl compounds show an alkylating capacity on 4-(p-nitrobenzyl)pyridine. The sequence of the alkylating potential was found to be acrylonitrile [ acrylamide [ acrylic acid [ acrolein (alkylation with acrolein was not observed after 3 weeks). The formation of adducts with acrylonitrile was approximately 10-and 100-fold faster than with acrylamide and acrylic acid, respectively, which is consistent with its highly carcinogenic and mutagenic activity. (2) 4-(p-Nitrobenzyl)pyridine alkylation reactions by vinyl compounds occur through an enthalpycontrolled Michael addition mechanism. The values for the free energy of activation for these reactions with 4-(p-nitrobenzyl)pyridine were: D à G°(37°C) acrylonitrile, 98 ± 1 kJ mol -1 ; acrylamide, 105 ± 2 kJ mol -1 ; acrylic acid, 109 ± 1 kJ mol -1 . (3) Application of Hammett treatment to the kinetic results revealed that these alkylation reactions occur through nucleophilic attack, being moderately accelerated by electron-withdrawing groups.

show abstract

Section: Introductionmentioning

confidence: 99%

The reactivity of vinyl compounds as alkylating agents

et al. 2012

Self Cite

View full text Add to dashboard Cite

show abstract

“…Alcohols, as cosolvents, can change the rate of organic, inorganic and enzymatic reactions. [1][2][3][4][5][6][7][8][9] Malachite green (MG + ) is a triphenylmethane dye. These dyes represent a class of dyes of commercial and analytical importance.…”

Section: Introductionmentioning

confidence: 99%

Kinetics of Malachite Green Fading in Water‐ethanol‐1‐propanol Ternary Mixtures

Samiey

Zafari

2012

J Chinese Chemical Soc

View full text Add to dashboard Cite

The rate constant of malachite green (MG + ) alkaline fading was measured in water-ethanol-1-propanol ternary mixtures. This reaction was studied under pseudo-first-order conditions at 283-303 K. It was observed that the reaction rate constant increases in the presence of different weight percentages of ethanol and 1-propanol. The fundamental rate constants of MG + fading in these solutions were obtained by SESMORTAC model. In each series of experiments, concentration of one alcohol was kept constant and the concentration of the second one was changed. It was observed that at constant concentration of one alcohol and variable concentrations of the second one, with increase in temperature, k 1 values increase and this indicates that presence of ethanol (or 1-propanol) increases dissolution of 1-propanol (or ethanol) in the activated complex formed in these solutions. Also, in each zone, fundamental rate constants of reaction at each certain temperature change as k k k 2 1 1 >> >> -.

show abstract

“…A correlation was found between their alkylating capacity and carcinogenicity . Although many aspects related to the worldwide use of sorbic acid and its salts as food preservatives have long been known, there is little quantitative knowledge about their alkylating potential (Pérez-Prior et al 2008). Finally, we should say that sodium sorbate is genotoxic to human lymphocytes.…”

Section: Discussionmentioning

confidence: 99%