Factors influencing benzene formation from the Decarboxylation of benzoate in liquid model systems

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 24, 2011, Pages 12975-12981

  Medeiros Vinci, Raquel ^a,b   De Meulenaer, Bruno ^a,b   Andjelkovic, Mirjana ^c   Canfyn, Michael ^c   Van Overmeire, Ilse ^c   Van Loco, Joris ^c  

^a GHENT UNIVERSITY   (Belgium)

^b Food2Know ^*  (Belgium)

^c SCIENTIFIC INSTITUTE OF PUBLIC HEALTH   (Belgium)

Author keywords

antioxidants; ascorbic acid; Benzene; benzoate; Cu 2+; hydroxyl radicals; metal chelation; model systems

Indexed keywords

ANTIOXIDANTS; ASCORBIC ACIDS; BENZOATE; HYDROXYL RADICALS; METAL CHELATION; MODEL SYSTEMS;

CARBOXYLATION; CHELATION; KETONES; LIQUIDS; METAL IONS; ORGANIC ACIDS; TRANSITION METAL COMPOUNDS; TRANSITION METALS;

BENZENE;

ANTIOXIDANT; ASCORBIC ACID; BENZENE; BENZOIC ACID DERIVATIVE; BUFFER; COPPER; HYDROXYL RADICAL; RIBOFLAVIN;

ARTICLE; CHEMISTRY; DECARBOXYLATION; FOOD; FOOD CONTAMINATION; LIGHT; PH; SOLUTION AND SOLUBILITY; SYNTHESIS;

ANTIOXIDANTS; ASCORBIC ACID; BENZENE; BENZOATES; BUFFERS; COPPER; DECARBOXYLATION; FOOD; FOOD CONTAMINATION; HYDROGEN-ION CONCENTRATION; HYDROXYL RADICAL; LIGHT; RIBOFLAVIN; SOLUTIONS;

EID: 84255176343     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf203233s     Document Type: Article

References (36)

1. IARC Benzene-IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Supplement 7. 1 to 42 ed.; International Agency for Research on Cancer: France, Lyon, 1987.
2. Mcneal, T. P.; Nyman, P. J.; Diachenko, G. W.; Hollifield, H. C. Survey of benzene in foods by using headspace concentration techniques and capillary gas-chromatography J. AOAC Int. 1993, 76 (6) 1213-1219
3. Nyman, P. J.; Diachenko, G. W.; Perfetti, G. A.; Mcneal, T. P.; Hiatt, M. H.; Morehouse, K. M. Survey results of benzene in soft drinks and other beverages by headspace gas chromatography/mass spectrometry J. Agric. Food Chem. 2008, 56 (2) 571-576
4. Lachenmeier, D. W.; Reusch, H.; Sproll, C.; Schoeberl, K.; Kuballa, T. Occurrence of benzene as a heat-induced contaminant of carrot juice for babies in a general survey of beverages Food Addit. Contam., Part A 2008, 25 (10) 1216-1224
5. Van Poucke, C.; Detavernier, C.; Van Bocxlaer, J. F.; Vermeylen, R.; Van Peteghem, C. Monitoring the benzene contents in soft drinks using headspace gas chromatography-mass spectrometry: A survey of the situation on the Belgian market J. Agric. Food Chem. 2008, 56 (12) 4504-4510
6. Fleming-Jones, M. E.; Smith, R. E. Volatile organic compounds in foods: A five year study J. Agric. Food Chem. 2003, 51 (27) 8120-8127
7. Barshick, S.; Smith, S.; Buchanan, M.; Guerin, M. Determination of benzene content in food using a novel blender purge and trap GC/MS method J. Food Compos. Anal. 1995, 8, 244-257
8. Lachenmeier, D. W.; Kuballa, T.; Reusch, H.; Sproll, C.; Kersting, M.; Alexy, U. Benzene in infant carrot juice: Further insight into formation mechanism and risk assessment including consumption data from the DONALD study Food Chem. Toxicol. 2010, 48 (1) 291-297
9. Masohan, A.; Parsad, G.; Khanna, M. K.; Chopra, S. K.; Rawat, B. S.; Garg, M. O. Estimation of trace amounts of benzene in solvent-extracted vegetable oils and oil seed cakes Analyst 2000, 125 (9) 1687-1689
10. Long, D. G. From cobalt to chloropropanol: de tribulationibus aptis cerevisiis imbibendis J. Inst. Brew. 1999, 105 (2) 79-84
11. Wu, Q. J.; Lin, H.; Fan, W.; Dong, J. J.; Chen, H. L. Investigation into benzene, trihalomethanes and formaldehyde in Chinese lager beers J. Inst. Brew. 2006, 112 (4) 291-294
12. Wittkowski, R.; Baltes, W.; Jennings, W. G. Analysis of liquid smoke and smoked meat volatiles by headspace gas-chromatography Food Chem. 1990, 37 (2) 135-144
13. Varner, S. L.; Hollifield, H. C.; Andrzejewski, D. Determination of benzene in polypropylene food-packaging materials and food-contact paraffin waxes J. Assoc. Off. Anal. Chem. 1991, 74 (2) 367-374
14. Knox, R. C.; Canter, L. W. Prioritization of ground water contaminants and sources Water Air and Soil Poll. 1996, 88 (3-4) 205-226
15. Ahn, D. U. Production of volatiles from amino acid homopolymers by irradiation J. Food Sci. 2002, 67 (7) 2565-2570
16. Gardner, L. K.; Lawrence, G. D. Benzene production from decarboxylation of benzoic-acid in the presence of ascorbic-acid and a transition-metal catalyst J. Agric. Food Chem. 1993, 41 (5) 693-695
17. EC European Parliament and Council Directive 95/2/EC of 20 February 1995 on Food Additives Other than Colours and Sweeteners, 1995.
18. Cao, X. L.; Casey, V. Improved method for the determination of benzene in soft drinks at sub-ppb levels Food Addit. Contam. 2008, 25 (4) 401-405
19. Nyman, P. J.; Wamer, W. G.; Begley, T. H.; Diachenko, G. W.; Perfetti, G. A. Evaluation of accelerated UV and thermal testing for benzene formation in beverages containing benzoate and ascorbic acid J. Food Sci. 2010, 75 (3) C263-C267
20. ICBA Guidance Document to Mitigate the Potential for Benzene Formation in Beverages; International Council of Beverages Association; Washington, DC, 2006.
21. AOCS Official Method Cd 18-90: p -Anisidine value. In Official Methods and Recommended Practices of the American Oil Chemists' Society, 4 th ed.; AOCS Press: Champaign, IL, 1989.
22. AOCS Official Method Cd 8b-90: Peroxide value, acetic acid-isooctane method. In Official Methods and Recommended Practices of the American Oil Chemists' Society, 4 th ed.; AOCS Press: Champaign, IL, 1989.
23. Medeiros Vinci, R.; Canfyn, M.; De Meulenaer, B.; de Schaetzen, T.; Van Overmeire, I.; De Beer, J.; Van Loco, J. Determination of benzene in different food matrices by distillation and isotope dilution HS-GC/MS Anal. Chim. Acta 2010, 672 (1-2) 124-129
24. Dodson, K. Y.; Young, E. R.; Soliman, A. G. M. Determination of total vitamin-C in various food matrices by liquid-chromatography and fluorescence detection J. AOAC Int. 1992, 75 (5) 887-891
25. Vandekinderen, I.; Van Camp, J.; Devlieghere, F.; Ragaert, P.; Veramme, K.; Bernaert, N.; Denon, Q.; De Meulenaer, B. Evaluation of the use of decontamination agents during fresh-cut leek processing and quantification of their effect on its total quality by means of a multidisciplinary approach Innov. Food Sci. Emerg. 2009, 10 (3) 363-373
26. Baker, M. S.; Gebicki, J. M. The effect of pH on yields of hydroxyl radicals produced from superoxide by potential biological iron chelators Arch. Biochem. Biophys. 1986, 246 (2) 581-588
27. Mahoney, J. R.; Graf, E. Role of alpha-tocopherol, ascorbic-acid, citric-acid and EDTA as oxidants in model systems J. Food Sci. 1986, 51 (5) 1293-1296
28. Sahbaz, F.; Somer, G. The effect of citrate anions on the kinetics of cupric ion catalyzed oxidation of ascorbic-acid Food Chem. 1993, 47 (4) 345-349
29. Imer, F.; Sonmezoglu, I. C.; Kozcaz, M. The role of buffers on the kinetics of L-ascorbic acid oxidation catalyzed by copper(II) Ital. J. Food Sci. 2003, 15 (4) 521-529
30. Kimoto, E.; Tanaka, H.; Ohmoto, T.; Choami, M. Analysis of the transformation products of dehydro- l -ascorbic acid by ion-pairing high-performance liquid-chromatography Anal. Bioch. 1993, 214 (1) 38-44
31. 2 production in cell-suspension cultures of Picea abies and in the absence of cells J. Exp. Bot. 2006, 57 (8) 1633-1644
32. Sahbaz, F.; Somer, G. Photosensitized decomposition of ascorbic acid in the presence of riboflavin Food Chem. 1993, 46 (2) 177-182
33. Jung, M. Y.; Kim, S. K.; Kim, S. Y. Riboflavin-sensitized photooxidation of ascorbic acid-Kinetics and amino acid effects Food Chem. 1995, 53 (4) 397-403
34. Khan, M. M. T.; Martell, A. E. Metal ion and metal chelate catalyzed oxidation of ascorbic acid by molecular oxygen. I. Cupric and ferric ion catalyzed oxidation J. Am. Chem. Soc. 1967, 89 (16) 4176-4185
35. Ogata, Y.; Kosugi, Y.; Morimoto, T. Kinetics of cupric salt-catalysed autoxidation of l -ascorbic acid in aqueous solutions Tetrahedron 1968, 24 (10) 4057-4066
36. Casado, F. J.; Sanchez, A. H.; De Castro, A.; Rejano, L.; Beato, V. M.; Montano, A. Fermented vegetables containing benzoic and ascorbic acids as additives: benzene formation during storage and impact of additives on quality parameters J. Agric. Food Chem. 2011, 59 (6) 2403-2409