10.1021/jf051330b.s001
Yair Bezman
Yair
Bezman
Itzhak Bilkis
Itzhak
Bilkis
Peter Winterhalter
Peter
Winterhalter
Peter Fleischmann
Peter
Fleischmann
Russell L. Rouseff
Russell L.
Rouseff
Susanne Baldermann
Susanne
Baldermann
Michael Naim
Michael
Naim
Thermal Oxidation of 9‘-<i>cis</i>-Neoxanthin in a Model System
Containing Peroxyacetic Acid Leads to the Potent Odorant
β-Damascenone
American Chemical Society
2005
peroxyacetic acid oxidation
Damascenone
peroxyacetic acid
damascenone
neoxanthin
Model System Containing Peroxyacetic
phase
min
formation
2005-11-16 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Thermal_Oxidation_of_9_i_cis_i_Neoxanthin_in_a_Model_System_Containing_Peroxyacetic_Acid_Leads_to_the_Potent_Odorant_Damascenone/3256903
The potent odorant β-damascenone was formed directly from 9‘-<i>cis</i>-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‘-<i>cis</i>-neoxanthin under optimal experimental condition.
The detailed pathway by which β-damascenone is formed remains to be elucidated.
Keywords: β-Damascenone; 9‘-<i>cis</i>-neoxanthin; peroxyacetic acid; epoxide; thermolysis