Skip to main content
SpringerLink
Log in

Sorbic Acid as an Alkylating Agent

  • SIMEC’06
  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

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 alk[H+][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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Thakur, B.R., Singh, K., Arya, S.S.: Chemistry of sorbates—a basic perspective. Food Rev. Int. 10, 71–91 (1994)

    Article  CAS  Google Scholar 

  2. Dacosta, Y.: L’acide sorbique et les sorbates. In: CDIUPA, Massy (1994)

    Google Scholar 

  3. U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition: FDA List of Food Additives that are Generally Recognized as Safe (GRAS). Rockville, MD (2005)

  4. Ferrand, C., Marc, F., Fritsch, P., Cassand, P., de Saint Blanquat, G.: Genotoxicity study of reaction products of sorbic acid. J. Agric. Food Chem. 48, 3605–3610 (2000)

    Article  CAS  Google Scholar 

  5. Münzer, R., Guigas, C., Renner, H.W.: Reexamination of potassium sorbate and sodium sorbate for possible genotoxic potential. Food Chem. Toxicol. 28, 397–401 (1990)

    Article  Google Scholar 

  6. Schlater, J., Würgler, F.E., Kränzlin, R., Maier, P., Hollinger, E., Graf, U.: The potential genotoxicity of sorbates: effects on cell cycle in vitro in V79 cells and somatic mutations in Drosophila. Food Chem. Toxicol. 30, 843–851 (1992)

    Article  Google Scholar 

  7. Würgler, F.E., Schlatter, J., Maier, P.: The genotoxicity status of sorbic acid, potassium sorbate and sodium sorbate. Mutat. Res. 283, 107–111 (1992)

    Article  Google Scholar 

  8. Wedzicha, B.L., Brook, M.A.: Reaction of sorbic acid with nucleophiles: preliminary studies. Food Chem. 31, 29–40 (1989)

    Article  CAS  Google Scholar 

  9. Khandelwal, G.D., Wedzicha, B.L.: Nucleophilic reactions of sorbic acid. Food Addit. Contam. 7, 685–694 (1990)

    CAS  Google Scholar 

  10. Verbiscar, A.J., Campbell, K.N.: Unsaturated six-membered ring lactams. J. Org. Chem. 29, 2472–2474 (1974)

    Article  Google Scholar 

  11. Khandelwal, G.D., Wedzicha, B.L.: Derivatives of sorbic acid-thiol reaction products. Food Chem. 37, 159–169 (1990)

    Article  CAS  Google Scholar 

  12. Kito, Y., Namiki, M., Tsuji, K.: A new N-nitropyrrole. 1,4-dinitro-2-methylpyrrole formed by the reaction of sorbic acid with sodium nitrite. Tetrahedron 34, 505–508 (1970)

    Google Scholar 

  13. Kim, J.H., Thomas, J.J.: Use of 4-(4-nitrobenzyl)pyridine (4-NBP) to test mutagenic potential of slow-reacting epoxides, their corresponding olefins, and other alkylating agents. Bull. Environ. Contam. Toxicol. 49, 879–885 (1992)

    Article  CAS  Google Scholar 

  14. Shephard, S.E., Lutz, W.K.: Nitrosation of dietary precursors. Cancer Surv. 8, 401–421 (1989)

    CAS  Google Scholar 

  15. García Santos, M.P., Calle, E., Casado, J.: Amino acid nitrosation products as alkylating agents. J. Am. Chem. Soc. 123, 7506–7510 (2001)

    Article  CAS  Google Scholar 

  16. García Santos, M.P., González Mancebo, S., Hernández Benito, J., Calle, E., Casado, J.: Reactivity of amino acids in nitrosation reactions and its relation to the alkylating potential of their products. J. Am. Chem. Soc. 124, 2177–2182 (2002)

    Article  CAS  Google Scholar 

  17. Pérez Prior, M.T., Manso, J.A., García Santos, M.P., Calle, E., Casado, J.: Reactivity of lactones and GHB formation. J. Org. Chem. 70, 420–426 (2005)

    Article  CAS  Google Scholar 

  18. Manso, J.A., Pérez Prior, M.T., García Santos, M.P., Calle, E., Casado, J.: A kinetic approach to the alkylating potential of carcinogenic lactones. Chem. Res. Toxicol. 18, 1161–1166 (2005)

    Article  CAS  Google Scholar 

  19. Pérez Prior, M.T., Manso, J.A., García Santos, M.P., Calle, E., Casado, J.: Alkylating potential of potassium sorbate. J. Agric. Food Chem. 53, 10244–10247 (2005)

    Article  CAS  Google Scholar 

  20. Tindall, G.W.: Mobile-phase buffers, part I: the interpretation of pH in partially aqueous mobile phases. LCGC North Am. 20, 1028–1032 (2002)

    CAS  Google Scholar 

  21. Eklund, T.: The antimicrobial effect of dissociated and undissociated sorbic acid at different pH levels. J. Appl. Bacteriol. 54, 383–389 (1983)

    CAS  Google Scholar 

  22. Food Safety & Hygiene, Bulletin for the Australian Food Industry, p. 2 (June 2003)

  23. Connors, K.A.: Chemical Kinetics The Study of Reaction Rates in Solution. VCH, New York (1990), pp. 208 and 246

    Google Scholar 

  24. Exner, O.: Correlation Analysis of Chemical Data. Plenum, New York (1988), Chap. 3

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Departamento de Química Física, Universidad de Salamanca, Plaza de la Merced, 37008, Salamanca, Spain

    M. Teresa Pérez-Prior, José A. Manso, M. del Pilar García-Santos, Emilio Calle & Julio Casado

Authors
  1. M. Teresa Pérez-Prior
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. José A. Manso
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. del Pilar García-Santos
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Emilio Calle
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Julio Casado
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Julio Casado.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pérez-Prior, M.T., Manso, J.A., del Pilar García-Santos, M. et al. Sorbic Acid as an Alkylating Agent. J Solution Chem 37, 459–466 (2008). https://doi.org/10.1007/s10953-008-9251-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-008-9251-9

Keywords

Search

Navigation