1 research outputs found
The Discovery of Citral-Like Thiophenes in Fried Chicken
The isomers of 3,7-dimethyl-2,6-octadienal,
more commonly known
together as citral, are two of the most notable natural compounds
in the flavor and fragrance industry. However, both isomers are inherently
unstable, limiting their potential use in various applications. To
identify molecules in nature that can impart the fresh lemon character
of citral while demonstrating stability under acidic and thermal conditions
has been a major challenge and goal for the flavor and fragrance industry.
In the study of fried chicken, several alkyl thiophenecarbaldehydes
were identified by gas chromatography–mass spectrometry and
gas chromatography–olfactometry that provided a similar citral-like
aroma. The potential mechanism of formation in fried chicken is discussed.
Furthermore, in order to explore the organoleptic properties of this
structural backbone, a total of 35 thiophenecarbaldehyde derivatives
were synthesized or purchased for evaluation by odor and taste. Certain
organoleptic trends were observed as the length of the alkyl or alkenyl
chain increased or when the chain was moved to different positions
on the thiophene backbone. The 3-substituted alkyl thiophenecarbaldehydes,
specifically 3-butyl-2-thiophenecarbaldehyde and 3-(3-methylbut-2-en-1-yl)-2-thiophenecarbaldehyde,
exhibited strong citrus and citral-like notes. Several alkyl thiophenecarbaldehydes
were tested in high acid stability trials (4 °C vs 38 °C)
and outperformed citral both in terms of maintaining freshness over
time and minimizing off-notes. Additional measurements were completed
to calculate the odor thresholds for a select group of thiophenecarbaldehydes,
which were found to be between 4.7–215.0 ng/L in air