Fate of damascenone in wine: The role of SO2

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 26, 2004, Pages 8127-8131

  Daniel, Merran A ^a,b,c   Elsey, Gordon M ^a,b,c   Capone, Dimitra L ^b,c   Perkins, Michael V ^a,c   Sefton, Mark A ^b,c  

^a FLINDERS UNIVERSITY   (Australia)

^b AUSTRALIAN WINE RESEARCH INSTITUTE   (Australia)

^c Adelaide Laboratory   (Australia)

Author keywords

Bicyclodamascenone; Damascenone; Degradation; Nucleophilic components; Sulfonic acid; Sulfur dioxide

Indexed keywords

4,9,9 TRIMETHYL 8 METHYLENEBICYCLO[3.3.1]NON 6 EN 2 ONE; ACETIC ACID; ACID; ALCOHOL; BICYCLO COMPOUND; CYSTEINE; DAMASCENONE; ETHYLAMINE; FLAVORING AGENT; MERCAPTOETHANOL; NEOXANTHIN; SULFONIC ACID DERIVATIVE; SULFUR DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; GAS CHROMATOGRAPHY; HEAT; HEATING; MASS SPECTROMETRY; MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; VALIDATION PROCESS; WINE;

EID: 11144220440     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf048582h     Document Type: Article

References (13)

1. Pickenhagen, W. In Flavor Chemistry-Thirty Years of Progress; Teranishi, E. L. W., Hornstein. I., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999; pp 75-87.
2. Aznar, M.; López, R.; Cacho, J.; Ferreira, V. Prediction of aged red wine aroma properties from aroma chemical composition. Partial least squares regression models. J. Agric. Food Chem. 2003, 51, 2700-2707.
3. Guth, H. Quantitation and sensory studies of character impact odorants of different white wine varieties. J. Agric. Food Chem. 1997, 45, 3027-3032.
4. Buttery, R. G.; Teranishi, R.; Ling, L. Identification of damascenone in tomato volatiles. Chem. Ind. 1988, 238.
5. Winterhalter, P.; Rouseff, R. Carotenoid-derived aroma compounds: an introduction. Carotenoid-Derived Aroma Compounds; Winterhalter, P., Rouseff, R., Eds.; ACS Symposium Series 802; American Chemical Society. Washington, DC, 2002; pp 1-17.
6. Guth, H. Comparison of different white wine varieties in odor profiles by instrumental analysis and sensory studies. In The Chemistry of Wine Flavor, Waterhouse, A. L., Ebeler, S. E., Eds.; ACS Symposium Series 714; American Chemical Society: Washington, DC, 1999; pp 39-54.
7. Demole, E.; Enggist, P. A chemical study of Virginia tobacco flavor (Nicotiana tabacum L.). I. Isolation and synthesis of two bicyclodamascenones. Helv. Chim. Acta 1976, 59, 1938-1943.
8. 3] β-ionone for quantification in grapes, juices and wines. J. Chromatogr. A 1998, 824, 71-78.
9. Phaff, R.; Bischofberger, N.; Mathies, P.; Petter, W.; Frei, B.; Jeger, O. Carbonyl vs. epoxyketone photochemistry: Photolysis of 1,2;3,4-diepoxy-2,6,6- trimethyl-1-cyclohexyl methyl ketone. Helv. Chim. Acta 1985, 68, 1204-1216.
10. Skouroumounis, G. K.; Sefton, M. A. Acid-catalyzed hydrolysis of alcohols and their β-D-glucopyranosides. J. Agric. Food Chem. 2000, 48, 2033-2039.
11. Pfoertner, v. K.-H. Substituted alkyl sulfonates by addition of sodium hydrogen sulfide to chalcones. Helv. Chim. Acta 1980, 63, 664-667.
12. Pitman, I. H.; Sternson, L. A. Method for estimating the equilibrium constants for covalent addition of nucleophilic reagents to heteroaromatic molecules. J. Am. Chem. Soc. 1976, 98, 5234-5238.
13. Capone, D. L.; Simpson, R. F.; Cox, A.; Duncan, B.; Skouroumounis, G. K.; Sefton M. A. New insights into wine bottle closure performance-flavour 'scalping' and cork taint. In Proceedings of the 12th Australian Wine Industry Technical Conference; Blair, R. J., Pretorius, I. S., Eds.; Australian Wine Industry Technical Conference: Adelaide, SA, 2004; in press.