Iron(III) tartrate as a potential precursor of light-induced oxidative degradation of white wine: Studies in a model wine system

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 8, 2011, Pages 3575-3581

  Clark, Andrew C ^a   Dias, Daniel A ^b   Smith, Trevor A ^b   Ghiggino, Kenneth P ^b   Scollary, Geoffrey R ^b  

^a CHARLES STURT UNIVERSITY   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

degradation of tartaric acid; glyoxylic acid production; Iron(III) tartrate; photoactivation; white wine oxidation; wine bottle color

Indexed keywords

GLYOXYLIC ACID PRODUCTION; PHOTOACTIVATION; TARTARIC ACIDS; WHITE WINE OXIDATION; WINE BOTTLE COLOR;

ARC LAMPS; BOTTLES; DEGRADATION; GLASS; IRON; IRON COMPOUNDS; OXIDATION;

WINE;

FERRIC ION; GLYOXYLIC ACID; GLYOXYLIC ACID DERIVATIVE; TARTARIC ACID DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; ION EXCHANGE CHROMATOGRAPHY; LIGHT; METHODOLOGY; OXIDATION REDUCTION REACTION; ULTRAVIOLET SPECTROPHOTOMETRY; WINE;

CHROMATOGRAPHY, ION EXCHANGE; FERRIC COMPOUNDS; GLYOXYLATES; LIGHT; MODELS, CHEMICAL; OXIDATION-REDUCTION; SPECTROPHOTOMETRY, ULTRAVIOLET; TARTRATES; WINE;

EID: 79955005102     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf104897z     Document Type: Article

References (35)

1. Jackson, R. S. Wine Science: Principles and Applications; Academic Press: Burlington, MA, 2008; pp 431 - 432.
2. Li, H.; Guo, A.; Wang, H. Mechanisms of oxidative browning of wine Food Chem. 2008, 108, 1-13
3. Berg, H. W.; Akiyoshi, M. Some factors involved in browning of white wines Am. J. Enol. Vitic. 1956, 7 (1) 1-7
4. Oszmianski, J.; Cheynier, V.; Moutounet, M. Iron-catalyzed oxidation of (+)-catechin in model systems J. Agric. Food Chem. 1996, 47 (4) 1712-1715 (Pubitemid 126646186)
5. Danilewicz, J. C. Review of reaction mechanisms of oxygen and proposed intermediate reduction products in wine: Central role of iron and copper Am. J. Enol. Vitic. 2003, 54, 73-85 (Pubitemid 36689421)
6. Waterhouse, A.; Laurie, V. Oxidation of wine phenolics: A critical evaluation and hypothesis Am. J. Enol. Vitic. 2006, 57, 306-313 (Pubitemid 44496961)
7. Ferreira, S. L. C.; Ferreira, H. S.; de Jesus, R. M.; Santos, J. V. S.; Brandao, G. C.; Souza, A. S. Development of method for the speciation of inorganic iron in wine samples Anal. Chim. Acta 2007, 602, 89-93 (Pubitemid 47532006)
8. Costa, R. C. C.; Araújo, A. N. Determination of Fe(III) and total Fe in wines by sequential injection analysis and flame atomic absorption spectrometry Anal. Chim. Acta 2001, 438, 227-233 (Pubitemid 32579185)
9. Tasev, K.; Karadjova, I.; Arpadjan, S.; Cvetkovic, J.; Stafilov, T. Liquid/liquid extraction and column solid phase extraction procedures for iron species determination in wines Food Control 2006, 17, 484-488 (Pubitemid 41829429)
10. Weber, G. Speciation of iron using HPLC with electrochemical and flame-AAS detection Fresenius' J. Anal. Chem. 1991, 340, 161-165
11. Paleologos, E. K.; Giokas, D. L.; Tzouwara-Karayanni, S. M.; Karayannis, M. I. Micelle mediated methodology for the determination of free and bound iron in wines by flame atomic absorption spectrometry Anal. Chim. Acta 2002, 458, 241-248 (Pubitemid 34273840)
12. Fenton, H. Oxidation of tartaric acid in presence of iron J. Chem. Soc. 1894, 65, 899-910
13. Fenton, H.; Jackson, H. The oxidation of polyhydric alcohols in presence of iron J. Chem. Soc., Trans. 1899, 75, 1-11
14. Benrath, A. Reactions photochimiques en solutions aqueous J. Prakt. Chem. 1917, 96, 190-201
15. Baraud, J. E. Étude des dérivés naturels de lacide tartrique Ann. Chim. 1954, 9, 535-604
16. Elias, R. J.; Waterhouse, A. Controlling the Fenton reaction in wine J. Agric. Food Chem. 2010, 58 (3) 1699-1707
17. Es-Safi, N.-E.; Guernevé, C. L.; Labarbe, B.; Fulcrand, H.; Cheynier, V.; Moutounet, M. Structure of a new xanthylium salt derivative Tetrahedron Lett. 1999, 40 (32) 5869-5872 (Pubitemid 29343843)
18. Es-Safi, N.-E.; Le Guernevé, C.; Fulcrand, H.; Cheynier, V.; Moutounet, M. Xanthylium salts formation involved in wine colour changes Int. J. Food Sci. Technol. 2000, 35 (1) 63-74
19. Drinkine, J.; Glories, Y.; Saucier, C. (+)-Catechin-aldehyde condensations: Competition between acetaldehyde and glyoxylic acid J. Agric. Food Chem. 2005, 53 (19) 7552-7558 (Pubitemid 41413554)
20. George, N.; Clark, A. C.; Prenzler, P. D.; Scollary, G. R. Factors influencing the production and stability of xanthylium cation pigments in a model white wine system Aust. J. Grape Wine Res. 2006, 12 (1) 57-68
21. Maury, C.; Clark, A. C.; Scollary, G. R. Determination of the impact of bottle colour and phenolic concentration on pigment development in white wine stored under external conditions Anal. Chim. Acta 2010, 60 (1-2) 81-86
22. Fulcrand, H.; Cheynier, V.; Oszmianski, J.; Moutounet, M. An oxidized tartaric acid residue as a new bridge potentially competing with acetaldehyde in flavan-3-ol condensation Phytochemistry 1997, 46 (2) 223-227 (Pubitemid 27391129)
23. Clark, A. C.; Prenzler, P. D.; Scollary, G. R. Impact of the condition of storage of tartaric acid solutions on the production and stability of glyoxylic acid Food Chem. 2007, 102 (3) 905-916 (Pubitemid 46108296)
24. Ware, M. Cyanotype; National Museum Photography, Film and Television: West Yorkshire, U.K., 1999; p 27 and 153.
25. Abrahamson, H. B.; Rezvani, A. B.; Brushmiller, J. G. Photochemical and spectroscopic studies of complexes, of iron(III) with citric acid and other carboxylic acids Inorg. Chim. Acta 1994, 226 (1-2) 117-127
26. Clark, A. C.; Pedretti, F.; Prenzler, P. D.; Scollary, G. R. Impact of ascorbic acid on the oxidative colouration and associated reactions of a model wine solution containing (+)-catechin, caffeic acid and iron Aust. J. Grape Wine Res. 2008, 14 (3) 238-249
27. Clark, A. C.; Scollary, G. R. Influence of light exposure, ethanol and copper(II) on the formation of a precursor for xanthylium cations from tartaric acid Aust. J. Grape Wine Res. 2003, 9 (1) 64-71
28. Navarre, C. LOenologie; Lavoisier Tec and Doc: Paris, France, 1991; p 322.
29. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry; John Wiley and Sons: New York, 1988; p 713 and 757.
30. Bobtelsky, M.; Jordan, J. The structure and behaviour of ferric tartrate and citrate complexes in dilute solutions J. Am. Chem. Soc. 1947, 69 (10) 2286-2290
31. Green, R. W.; Parkins, G. M. Complexes of iron with d -tartaric and meso -tartaric acids J. Phys. Chem. 1961, 65 (9) 1658-1659
32. Timberlake, C. F. Iron-tartrate complexes J. Chem. Soc. 1964, 1229-1240
33. Gallet, J.-P.; P̌aris, R. A. Etude thermometrique de la formation des complexes du fer(III), de laluminium et du gallium. Tartrates et citrates Anal. Chim. Acta 1967, 39 (C) 341-348
34. Hanby, J. R.; Johnson, D. C. Bond structure in the alkaline ferric-tartrate system J. Polym. Sci., Part A-1: Polym. Chem. 1969, 7 (10) 2983-2994
35. Legrini, O.; Oliveros, E.; Braun, A. M. Photochemical processes for water treatment Chem. Rev. 1993, 93, 671-698