An evaluation of methyl 2-oxocyclopentanecarboxylate as an iron(III) trap: Food perspectives

International Journal of Food Science and Technology

Volumn 41, Issue 1, 2006, Pages 57-65

  Blanco, Carlos ^a   Rojas, Antonio ^a   Caballero, Isabel ^a   Alvarez, Inmaculada ^a   Armentia, Alicia ^b  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b HOSPITAL UNIVERSITARIO RÍO HORTEGA   (Spain)

Author keywords

Biostability of metal complexes; Chelation; Complexation kinetics; Keto enol equilibrium of ketoester derivatives; Reaction mechanism

Indexed keywords

EID: 33645131393     PISSN: 09505423     EISSN: 13652621     Source Type: Journal    
DOI: 10.1111/j.1365-2621.2005.01036.x     Document Type: Article

References (42)

1. Bañares, M.A., Angoso, A., Manzano, J.L., Macias, B. & Rives, V. (1984). Spectroscopic study of complexes between cobalt(II) and nickel(II) with ethyl alpha-ketocyclopentylcarboxylate. Spectroscopy-Letters, 17, 197-205.
2. Bañares, M.A., Angoso, A., Manzano, J.L., Rodriguez, E. & Blasco, M.T. (1987). Synthesis and characterization of several lanthanide complexes with ethyl-ketocyclopentyl carboxylate. Inorganka Chimica Acta, 139, 135-136.
3. Bel-Rhlid, R., Fauve, A., Renard, M.F. & Veschambre, H. (1992). Microbiological reduction of carbonyl groupings: preparation of stereoisomeric acyclic chiral diols. Biocatalysis, 6, 319-337.
4. Blanco, C.A. (1998). Coordination abilities in aqueous 1ratio1 metal chelates of 1,3-dicarbonylic ligands: absolute hardness and absolute electronegativity. Journal of Chemical Society. Perkin Transaction 2, 12, 2741-2744.
5. (III) metal ions. New Journal of Chemistry, 18, 223-229.
6. Blanco, C.A., Caballero, I., Rojas, A., Gómez, M. & Alvarez, J. (2003). Chelation of aqueous iron(III) by 2-acetyl-1,3-cyclohexanedione and beer ageing. Food Chemistry, 81, 561-568.
7. Bocca, B., Alimonti, A., Coni, E. et al. (2000). Determination of the total content and binding pattern of elements in human milk by high-performance liquid chromatography-inductively coupled plasma-atomic emission-spectrometry. Talanta, 53, 295-303.
8. Boudaud, N. & Dumont, J.P. (1996). Interaction between flavor components and ß-lactoglobulins. Flavor-Food Interactions, 633, 90-96.
9. Chambers, R.D. & Greenhall, M.P. (1996). Direct fluorination of 1,3-dicarbonyl compounds. Tetrahedron, 52, 1-8;
10. Chambers, R.D. & Greenhall, M.P. (2001). Reactions involving fluoride ion. Reactions of dialkyl acetylene dicarboxylates. Journal of Fluorine Chemistry, 107, 171-176.
11. Doonan, S. (1969). In: The Chemistry of Carboxylic Acids and Esters (edited by H. Patay). Pp. 923-1054. London: Interscience-Publishers.
12. Ebraheem, K.A.K., Hamdi, S.T. & Khalaf, MM. (1981). Fluorinated beta-dikctones and their metal-chelates.1. Effect of ring strain on the direction of enolization of 2-trifluoroacetylcycloalkanones. Canadian Journal of Spectroscopy, 26, 225-229.
13. Eigen, M. & Maeyer, L.C. (1963). In: Technique of Organic Chemistry, Vol. VIII, Part II S (edited by L. Friess, E.S. Lewis & A. Weissberger). Pp. 890-900. New York, NY: Interscience.
14. Ema, T., Sugiyama, Y., Fukumoto, M. et al. (1998). Highly enantioselective reduction of carbonyl compounds using a reductase purified from Bakers' yeast. Journal of Organic Chemistry, 63, 4996-5000.
15. Geraldes, C., Barros, M.T., Maycock, C.D. & Silva, M.I. (1990). The preferential direction of enolization of some asymmetric 1,3-dicarbonyl compounds in solution: a study by multinuclear NMR spectroscopy. Journal of Molecular Structure, 238, 335-346.
16. Guth, H. & Grosh, W. (1989). 3-methylnonane-2,4-dione an intense odour compound formed during flavour reversion of soya-bean oil. Fat Science and Technology, 91, 225230.
17. Guth, H. & Grosh, W. (1991). Detection of furanoid fatty acids in soya bean oil- cause for the light-induced off flavour. Fat Science and Technology, 93, 249-255.
18. Guthrie, J.P. (1979). Enol content of simple carbonyl compounds. Approach based upon pKa estimation. Canadian Journal of Chemistry, 57, 1177-1185.
19. Hashem, E.Y. & Abubakr, M.S. (2000). Complex formation equilibria of iron (III) with 2-hydroxy-3-pyridinol and 2-mercapto-3-pyridinol. Spectrophotometric determination of iron (III) in multivitamins. Analytical Letters, 33, 691-707.
20. Hurrell, R.F., Reddy, MB., Burri, J. & Cook, J.D. (2000). An evaluation of EDTA compounds for iron fortification of cereal-based foods. British Journal of Nutrition, 84, 903-910.
21. Inoue, M., Hashimoto, K., Kuwahara, T., Sugimoto, Y., Uesako, T. & Funato, T. (1992). Preparation of pyrazolo [1,5-a]pyrimidine derivatives anti-inflammatory agents. (Otsuka Pharmaceutical Co., Ltd.) PCT Int. Appl. WO 92 18,504 (Cl. C07D487/04) 29 Oct. 1992)JP. Apl. 91/90, 707, 22 Apr 1991. 48pp.
22. Iyengar, G.V. & Nair, P.P. (2000). Global outlook on nutrition and the environment: meeting the challenges of the next millennium. Science Total Environment, 249, 331-336.
23. Jang, J.T., Green, J.B., Beard, J.L. & Green, M.H. (2000). Kinetic analysis shows that iron deficiency decreases liver vitamin A mobilization in rats. Journal of Nutrition, 130, 1291-1296.
24. Job, P. (1928). Formation and stability of inorganic complexes in solution. Annali di Chimica, 9, 113-203.
25. Johansson, A. (1970). Automatic titration by stepwise addition of equal volumes of titrant. Basic principles. Analyst (London), 95, 535-540.
26. Jorhem, L. & Engman, J. (2000). Determination of lead, cadmium, zinc, copper and iron in foods by atomic absorption spectrometry after microwave digestion. Journal of AOAC International, 83, 1189-1195.
27. Kallury, R.K., Krull, U.J. & Thompson, M. (1987). Synthesis of phospholipids suitable for covalent binding to surfaces. Journal of Organic Chemistry, 52, 5478-5480.
28. Khoe, G.H., Brown, P.L., Sylva, R.N. & Rovins, R.G. (1986). The hydrolysis of metal ions. Part 9. Iron(III) in perchlorate, nitrate and chloride media. Journal of Chemical Society, Dalton Transaction, 9, 1901-1906.
29. Kol'tsov, A.I. & Kheifets, G.M. (1971). Investigation of keto-enol tautomerism by nuclear magnetic resonance spectroscopy. Russian Chemical Review, 40, 773-788.
30. Makinen, M.W. & Brady, M.J. (2002). Structural origins of the insulin-mimetic effect of bis(acetylacetonato)oxo-vanadium(IV). Journal of Biological Chemistry, 277, 12215-12220.
31. Maroni, P. & Calmon, J.P. (1964). Spectrophotometric determination of the pK dissociation of ß-diketones. Technique and use of graphic methods. Bulletin de la Société Chimique de France, 519-524.
32. Mills, S.G. & Beak, P. (1985). Solvent effects on keto-enol equilibria: tests of quantitative models. Journal of Organic Chemistry, 50, 1216-1224.
33. Mozaz, S.R., Sotro, A.G., Segovia, J.G. & Azpilicueta, C.A. (1999). Influence of decantation of viura must on the cation content. Evolution during wine fermentation and stabilization. Food Research International, 32, 683-689.
34. Palaty, J. & Abbott, F.S. (1995). Structure-activity relationships of unsaturated analogs of valproic acid. Journal of Medicinal Chemistry, 38, 3398-3406.
35. Park, J. & Brittin, H.C. (2000). Iron content sensory evaluation, and consumer acceptance of food cooked in iron utensil. Journal of Food Quality, 23, 205.
36. Poucheret, P., Verma, S., Grynpas, M.D. & MaNeill, J.H. (1998). Vanadium and diabetes. Molecular and Cellular Biochemistry, 188, 73-80.
37. Rhoads, S.J. (1966). Nuclear magnetic resonance studies of enolizable cyclic ß-keto esters. Journal of Organic Chemistry, 31, 171-174.
38. Rose, J. (1961). Dynamic Physical Chemistry. Pp. 501-510. Londres: Pitman.
39. Satroutdinov, A.D., Dedyukhina, E.G., Chistyakova, T.E. et al. (2000). Degradation of metal-EDTA complexes by resting cells of the bacterial strain DSM 9103. Environmental Science and Technology, 34, 1715-1720.
40. Sutin, N., Jafte, M.R., Fay, D.P. & Cefola, M. (1971). Kinetics and mechanism of the formation of the monothenoyltrifluoroacetone complexes of nickel(II), cobalt(II), copper(II), and iron(III). Journal of the American Chemical Society, 93, 2878-2886.
41. Svendsen, R. & Lund, W. (2000). Speciation of Cu, Fe and Mn in beer using ion-exchange separation and size exclusion chromatography in combination with electrothermal atomic absorption spectrometry. Analyst, 125, 1933-1946.
42. Zeng, Z.T. & Jewsbury, R.A. (2000). Fluorometric-determination of iron using 5-(4-methoxyphenylazo)-8(4-toluenesulfoamido)quinoline. Analyst, 125, 1661-1665.