TY - CHAP
T1 - Influence of Structural Modification and Chirality on the Odor Potency and Odor Quality of Thiols
AU - Schoenauer, Sebastian
AU - Polster, Johannes
AU - Schieberle, Peter
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015
Y1 - 2015
N2 - Due to their extremely low odor thresholds, thiols often show a major impact on the overall aroma of foods, even if present in trace amounts. However, odor qualities as well as odor thresholds of thiols are often influenced by carbon chain length and chirality. In order to get a deeper insight into structure-odor correlations, different series of chiral mercapto-containing key aroma compounds and their homologues were synthesized, such as 3-mercaptoalkyl acetates and 3-mercaptoalkan-1-ols. Enantiomers were separated and their odor qualities and odor thresholds were determined. Absolute configurations were elucidated using a chiral derivatizing agent and 1H NMR anisotropy methods.
AB - Due to their extremely low odor thresholds, thiols often show a major impact on the overall aroma of foods, even if present in trace amounts. However, odor qualities as well as odor thresholds of thiols are often influenced by carbon chain length and chirality. In order to get a deeper insight into structure-odor correlations, different series of chiral mercapto-containing key aroma compounds and their homologues were synthesized, such as 3-mercaptoalkyl acetates and 3-mercaptoalkan-1-ols. Enantiomers were separated and their odor qualities and odor thresholds were determined. Absolute configurations were elucidated using a chiral derivatizing agent and 1H NMR anisotropy methods.
UR - http://www.scopus.com/inward/record.url?scp=84948697438&partnerID=8YFLogxK
U2 - 10.1021/bk-2015-1212.ch010
DO - 10.1021/bk-2015-1212.ch010
M3 - Chapter
AN - SCOPUS:84948697438
T3 - ACS Symposium Series
SP - 135
EP - 146
BT - Importance of Chirality to Flavor Compounds
A2 - Takeoka, Gary
A2 - Engel, Karl-Heinz
PB - American Chemical Society
ER -