Lipid-derived aldehyde degradation under thermal conditions

•Mono- and di-unsaturated lipid-derived aldehydes are degraded thermally.•The reaction produces formaldehyde, acetaldehyde and the breakage of double bonds.•The activation energy (Ea) of double bond breakage was determined (25kJ/mol).•This Ea was similar for C2C3 and C4C5 double bonds.•Nevertheless,...

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Bibliographic Details
Published in:Food chemistry 2015-05, Vol.174, p.89-96
Main Authors: Zamora, Rosario, Navarro, José L., Aguilar, Isabel, Hidalgo, Francisco J.
Format: Article
Language:English
Subjects:
2,4-Alkadienals
2-Alkenals
Acetaldehyde
Aldehyde degradation
Aldehydes
Aldehydes - chemistry
Alkanals
Bonding
Breakage
Carbonyls
Degradation
Food flavours
Foods
Hot Temperature
Lipid oxidation
Lipids - chemistry
Nucleophiles
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Summary:•Mono- and di-unsaturated lipid-derived aldehydes are degraded thermally.•The reaction produces formaldehyde, acetaldehyde and the breakage of double bonds.•The activation energy (Ea) of double bond breakage was determined (25kJ/mol).•This Ea was similar for C2C3 and C4C5 double bonds.•Nevertheless, alkanals were produced to a higher extent than 2-alkenals. Nucleophilic degradation produced by reactive carbonyls plays a major role in food quality and safety. Nevertheless, these reactions are complex because reactive carbonyls are usually involved in various competitive reactions. This study describes the thermal degradation of 2-alkenals (2-pentenal and 2-octenal) and 2,4-alkadienals (2,4-heptadienal and 2,4-decadienal) in an attempt to both clarify the stability of aldehydes and determine new compounds that might also play a role in nucleophile/aldehyde reactions. The obtained results showed that alkenals and alkadienals decomposed rapidly in the presence of buffer and air to produce formaldehyde, acetaldehyde, and the aldehydes corresponding to the breakage of the carboncarbon double bonds: propanal, hexanal, 2-pentenal, 2-octenal, glyoxal, and fumaraldehyde. The activation energy of double bond breakage was relatively low (∼25kJ/mol) and the yield of alkanals (10–18%) was higher than that of 2-alkenals (∼1%). All these results indicate that these reactions should be considered in order to fully understand the range of nucleophile/aldehyde adducts produced.
ISSN:0308-8146
1873-7072
DOI:10.1016/j.foodchem.2014.11.034