Model studies on the oxygen-induced formation of benzaldehyde from phenylacetaldehyde using pyrolysis GC-MS and FTIR

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 22, 2008, Pages 10697-10704

  Fong, Lam Chu ^a   Yaylayan, Varoujan A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Benzaldehyde; FTIR analysis; Oxidation of phenylacetaldehyde; Oxidative pyrolysis; Phenethylamine; Phenylacetaldehyde; Phenylalanine; Phenylpyruvic acid

Indexed keywords

ACETALDEHYDE; BENZALDEHYDE; BENZALDEHYDE DERIVATIVE; DRUG DERIVATIVE; OXYGEN; PHENYLACETALDEHYDE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; GLYCATION; HEAT; INFRARED SPECTROSCOPY; MASS FRAGMENTOGRAPHY; METHODOLOGY; SYNTHESIS;

ACETALDEHYDE; BENZALDEHYDES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HOT TEMPERATURE; MAILLARD REACTION; MODELS, CHEMICAL; OXYGEN; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

PRUNUS DULCIS;

EID: 57849123306     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8022468     Document Type: Article

References (17)

1. Chandra, A.; Nair, M. G. Quantification of benzaldehyde and its precursors in Montmorency cherry (Prunus cerasus L.) kernels. Phytochem. Anal. 1993, 4, 120-123.
2. Porter, D. J.; Bright, H. J. The cyanogenic substrate for horseradish peroxidase is a conjugated enamine. J. Biol. Chem. 1987, 262, 9154-9.
3. Okrasa, K.; Guibe-Jampel, E.; Plenkiewicz, J.; Therisod, M. In vitro bi-enzymatic synthesis of benzaldehyde from phenylalanine: practical and mechanistic studies. J. Mol. Catal. B: Enzym. 2004, 31, 97-101.
4. Severin, T.; Braeutigam, K. H. Formation of benzaldehyde from phenylalanine and N-acetylpheny lemylamine by heating under and air blast. Z. Lebensm.-Unters. -Forsch. 1970, 144, 321-323.
5. Granvogl, M.; Bugan, S.; Schieberle, P. Formation of amines and aldehydes from parent amino acids during thermal processing of cocoa and model systems: new insights into pathways of Strecker reaction. J. Agric. Food Chem. 2006, 54, 1730-1739.
6. Zamaro, R.; Navarro, J. L.; Gallardo, E.; Hidalgo, F. J. Chemical conversion of α-amino acids into α-keto acids by 4,5-epoxy-2-decenal. J. Agric. Food Chem. 2006, 54, 6101-6105.
7. Kato, Y. Influence of butter and or vegetable oil on flavours of roux prepared from wheat flour and fat/oil. Food Sci. Technol. Res. 2005, 11, 278-287.
8. Bravo, A.; Herrera, C. J.; Scherer, E.; Ju-Nam, Y.; Rübsam, H.; Madrid, J.; Zufall, C.; Rangel-Aldao, R. Formation of α-dicarbonyl compounds in beer during storage of pilsner. J. Agric. Food Chem. 2008, 56, 4134-4144.
9. Brinkman, H. W.; Copier, H.; de Leuw, J. J. M.; Tjan, S. B. Components contributing to the beef flavor. Analysis of headspace volatiles of beef broth. J. Agric. Food Chem. 1972, 20, 177-181.
10. Yaylayan, V. A.; Haffenden, L.; Chu, F. L.; Wnorowski, A. Oxidative pyrolysis and postpyrolytic derivatization techniques for the total analysis of Maillard model systems: investigation of control parameters of Maillard reaction pathways. Ann. N.Y. Acad. Sci. 2005, 1043, 41-54.
11. 13C]glucose model systems. J. Agric. Food Chem. 2001, 49, 800-803.
12. Chu, F. L.; Yaylayan, V. A. Post-Schiff base chemistry of the Maillard reaction: mechanism of imine isomerization. Ann. N.Y. Acad. Sci. 2008, 1126, 30-37.
13. Tokunaga, M.; Shirogane, Y.; Aoyama, H.; Obora, Y.; Tsuji, Y. Copper-catalyzed oxidative cleavage of carbon-carbon double bond of enol ethers with molecular oxygen. J. Organomet. Chem. 2005, 690, 5378-5382.
14. Kaneda, K.; Itoh, T.; Kii, N.; Jitsukawa, K.; Teranishi, S. Oxygenation of enamines using copper catalysts. J. Mol. Catal. 1982, 15, 349-365.
15. Gollnick, K.; Knutzen-Mies, K. Dye-sensitized photooxygenation of 2,3-dihydrofurans: competing [2+2]cycloadditions and ene reactions of singlet oxygen with a rigid cyclic enol ether system. J. Org. Chem. 1991, 56, 4017-4027.
16. Balci, M.; Taskesenligi, Y.; Harmandar, M. A novel dioxetane- hydroperoxide rearrangement: photooxygenation of 3-tert-butoxy (and methoxy)-6,7-benzobicyclo[3,2,1]octa-2,6-dienes. Tetrahedron Lett. 1989, 30, 3339-3342.
17. Horvat, Š.; Jakas, A. Peptide and amino acid glycation: new insights into the Maillard reaction. J. Pept. Sci. 2004, 10, 119-137.