Thermal Oxidation of 9‘-cis-Neoxanthin in a Model System Containing Peroxyacetic Acid Leads to the Potent Odorant β-Damascenone

The potent odorant β-damascenone was formed directly from 9‘-cis-neoxanthin in a model system by peroxyacetic acid oxidation and two-phase thermal degradation without the involvement of enzymatic activity. β-Damascenone formation was heavily dependent on pH (optimum at 5.0) and temperature, occurrin...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2005-11, Vol.53 (23), p.9199-9206
Main Authors: Bezman, Yair, Bilkis, Itzhak, Winterhalter, Peter, Fleischmann, Peter, Rouseff, Russell L, Baldermann, Susanne, Naim, Michael
Format: Article
Language:English
Subjects:
Biological and medical sciences
Buffers
Chromatography, High Pressure Liquid
Food industries
Fundamental and applied biological sciences. Psychology
Hot Temperature
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Models, Chemical
Norisoprenoids - chemistry
Odorants
Oxidation-Reduction
Oxygen - chemistry
Peracetic Acid - chemistry
Time Factors
Xanthophylls - chemistry
Xanthophylls - isolation & purification
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Summary:The potent odorant β-damascenone was formed directly from 9‘-cis-neoxanthin in a model system by peroxyacetic acid oxidation and two-phase thermal degradation without the involvement of enzymatic activity. β-Damascenone formation was heavily dependent on pH (optimum at 5.0) and temperature, occurring over the two sequential phases. The first was incubation with peroxyacetic acid at 60 °C for 90 min, and the second was at above 90 °C for 20 min. Only traces of β-damascenone were formed on application of only one of the two phases. Formate and citrate solutions produced a much better environment for β-damascenone formation than acetate and phosphate. About 7 μg/L β-damascenone was formed from 5.8 mg/L 9‘-cis-neoxanthin under optimal experimental condition. The detailed pathway by which β-damascenone is formed remains to be elucidated. Keywords: β-Damascenone; 9‘-cis-neoxanthin; peroxyacetic acid; epoxide; thermolysis
ISSN:0021-8561
1520-5118
DOI:10.1021/jf051330b