On the autoxidation of bitter-tasting Iso-α-acids in beer

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 8, 2010, Pages 5059-5067

  Intelmann, Daniel ^a   Hofmann, Thomas ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

acids; Alloisohumulone; Beer; Hop; Hydroperoxides; Iso ; Tricyclocohumol

Indexed keywords

ACID;

ARTICLE; BEER; CHEMISTRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION;

ACIDS; BEER; CHROMATOGRAPHY, LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; OXIDATION-REDUCTION;

HUMULUS;

EID: 77951287547     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf100083e     Document Type: Article

References (29)

1. De Cooman, L.; Aerts, G.; Overmeire, H.; De Keukeleire, D. Alterations of the profiles of iso-α-acids during beer ageing, marked instability of trans -iso-α-acids and implications for beer bitterness consistency in relation to tetrahydroiso-α-acids J. Inst. Brew. 2000, 106, 169-178
2. Pangborn, R. M.; Lewis, M. J.; Tanno, L. S. Sensory quantification of bitterness and flavour of beer during storage J. Inst. Brew. 1977, 83, 244-250
3. King, B. M.; Duineveld, C. A. A. Changes in bitterness as beer ages naturally Food Qual. Pref. 1999, 10, 315-324
4. Hughes, P. S.; Menneer, I. D.; Walters, M. T.; Marinova, G. Differential behaviour of cis- and trans-iso-α-acids Proc. 27th EBC-Congr. 1997, 26, 231-238
5. De Keukeleire, D.; Verzele, M. The absolute configuration of the isohumulones and the humulinic acids Tetrahedron 1971, 27, 4939-4945
6. Kowaka, M.; Kokubo, E. Composition of bitter substances of hops and characteristics of beer bitterness J. Am. Soc. Brew. Chem. 1976, 35, 16-21
7. Malowicki, M. G.; Shellhammer, T. H. Isomerization and degradation kinetics of hop (Humulus lupulus) acids in a model wort-boiling system J. Agric. Food Chem. 2005, 53, 4434-4439
8. Jaskula, B.; Kafarski, P.; Aerts, G.; De Cooman, L. A Kinetic study on the isomerization of hop α-acids J. Agric. Food Chem. 2008, 56, 6408-6415
9. Araki, S.; Takashio, M.; Shinotsuka, K. A new parameter for determination of the extent of staling in beer J. Am. Soc. Brew. Chem. 2002, 60, 26-30
10. Intelmann, D.; Batram, C.; Kuhn, C.; Haseleu, G.; Meyerhof, W.; Hofmann, T. Three TAS2R bitter taste receptors mediate the psychophysical responses to bitter compounds of hops (Humulus lupulus L.) and beer Chem. Percept. 2009, 2, 118-132
11. Fritsch, A.; Shellhammer, T. H. Alpha-acids do not contribute bitterness to lager beer J. Am. Soc. Brew. Chem. 2007, 65, 26-28
12. Malfliet, S.; Van Opstaele, F.; De Clippeleer, J.; Syryn, E.; Goiris, K.; De Cooman, L.; Aerts, G. Flavour instability of pale lager beers: Determination of analytical markers in relation to sensory ageing J. Inst. Brew. 2008, 114, 180-192
13. Jaskula, B.; Syryn, E.; Goiris, K.; De Rouck, G.; Van Opstaele, F.; De Clippeleer, J.; Aerts, G.; De Cooman, L. Hopping technology in relation to beer bitterness consistency and flavor stability J. Am. Soc. Brew. Chem. 2007, 65, 38-46
14. De Cooman, L.; Aerts, G.; Witters, A.; De Ridder, M.; Boeykens, A.; Goiris, K.; De Keukeleire, D. Comparative study of the stability of iso-α-acids, dihydroiso-α-acids and tetrahydroiso-α-acids during beer ageing Cerevisia 2001, 26, 155-160
15. Intelmann, D.; Haseleu, G.; Hofmann, T. LC-MS/MS quantitation of hop-derived bitter compounds in beer using the ECHO technique J. Agric. Food Chem. 2009, 57, 1172-1182
16. Malfliet, S.; Goiris, K.; Aerts, G.; De Cooman, L. Analytical-sensory determination of potential flavour deficiencies of light beers J. Inst. Brew. 2009, 115, 49-63
17. Intelmann, D.; Kummerlo we, G.; Haseleu, G.; Desmer, N.; Schulze, K.; Fröhlich, R.; Frank, O.; Luy, B.; Hofmann, T. Structures of storage-induced transformation products of the beer's bitter principle, revealed by sophisticated NMR and LC/MS techniques Chem. - Eur. J. 2009, 15, 13047-13058
18. 18O Stable isotope labeling, quantitative model experiments, and molecular dynamics simulation studies on the trans-specific degradation of the bitter tasting iso-α-acids of beer J. Agric. Food Chem. 2009, 57, 11014-11023
19. Clarke, B. J.; Hildebrand, R. P. The isomerization of humulone; III. The degradation of isohumulone J. Inst. Brew. 1967, 73, 282-293
20. Schulze, W. G.; Ting, P. L.; Henckel, L. A.; Goldstein, H. Separation of humulinic acids by reverse-phase high performance liquid chromatography J. Am. Soc. Brew. Chem. 1981, 39, 12-15
21. Diffor, D. W.; Ramos, E. S. A.; Hansen, G. L. Preparation of humulinic acid. Effect on analytical and flavor characteristics of beer Proc. Am. Soc. Brew. Chem. 1972, 109-114
22. De Keukeleire, D. Oxidation products of the hop α-acids and the iso-α-acids (in Dutch) Cerevisia 1981, 73-80
23. Vanhoey, M.; Vandewalle, M.; Verzele, M. Oxidation products of isohumulones Bull. Soc. Chim. Belg. 1970, 79, 499-509
24. Hashimoto, N.; Eshima, T. Oxidative degradation of isohumulones in relation to flavor stability of beer J. Inst. Brew. 1979, 85, 136-140
25. Corzo, O.; Bracho, N. Prediction oft the sensory quality of canned beer as determined by oxygen concentration, physical chemistry contents, and storage conditions J. Food Sci. 2004, 69, 285-289
26. Cann, M. R.; Davis, A.-M.; Shannon, P. V. R. New rearrangement and oxidation products from humulone J. Chem. Soc., Perkin Trans. 1 1982, 375-383
27. Giovanelli, G.; Brenna, O. V. Oxidative stability of red wine stored in packages with different oxygen permeability Eur. Food Res. Technol. 2007, 226, 169-179
28. Hertlein, J.; Bornarova, K.; Weisser, H. On the suitability of PET bottles for beer packaging (in German) Brauwelt 1997, 860-866
29. Alderweireldt, F.; Verzele, M.; Anteunis, M.; Dierckens, J. The isomerization products of humulone Bull. Soc. Chim. Belg. 1965, 74, 29-40