10.1021/jf300036a.s001 Corinna Dawid Corinna Dawid Andrea Henze Andrea Henze Oliver Frank Oliver Frank Anneke Glabasnia Anneke Glabasnia Mathias Rupp Mathias Rupp Kirsten Büning Kirsten Büning Diana Orlikowski Diana Orlikowski Matthias Bader Matthias Bader Thomas Hofmann Thomas Hofmann Structural and Sensory Characterization of Key Pungent and Tingling Compounds from Black Pepper (<i>Piper nigrum</i> L.) American Chemical Society 2016 Piper nigrum Tingling Compounds eicosa recognition thresholds chemical structure Sensory Characterization taste dilution analysis octadeca Black Pepper compound Key Pungent Sensory studies NMR nmol TDA structure determination 2016-02-21 17:02:04 Journal contribution https://acs.figshare.com/articles/journal_contribution/Structural_and_Sensory_Characterization_of_Key_Pungent_and_Tingling_Compounds_from_Black_Pepper_i_Piper_nigrum_i_L_/2538304 To gain a more comprehensive knowledge on whether, besides the well-known piperine, other compounds are responsible for the pungent and tingling oral impression imparted by black pepper, an ethanol extract prepared from black pepper (<i>Piper nigrum</i> L.) was screened for its key sensory-active nonvolatiles by application of taste dilution analysis (TDA). Purification of the compounds perceived with the highest sensory impact, followed by LC-MS and 1D/2D NMR experiments as well as synthesis, led to the structure determination of 25 key pungent and tingling phytochemicals, among which the eight amides 1-(octadeca-2<i>E</i>,4<i>E</i>,13<i>Z</i>-trienyl)­piperidine, 1-(octadeca-2<i>E</i>,4<i>E</i>,13<i>Z</i>-trienyl)­pyrrolidine, (2<i>E</i>,4<i>E</i>,13<i>Z</i>)-<i>N</i>-isobutyl-octadeca-2,4,13-trienamide, 1-(octadeca-2<i>E</i>,4<i>E</i>,12<i>Z</i>-trienoyl)-pyrrolidine, 1-(eicosa-2<i>E</i>,4<i>E</i>,15<i>Z</i>-trienyl)­piperidine, 1-(eicosa-2<i>E</i>,4<i>E</i>,15<i>Z</i>-trienyl)­pyrrolidine, (2<i>E</i>,4<i>E</i>,15<i>Z</i>)-<i>N</i>-isobutyl-eicosa-2,4,15-trienamide, and 1-(eicosa-2<i>E</i>,4<i>E</i>,14<i>Z</i>-trienoyl)-pyrrolidine were not yet reported in literature. Sensory studies by means of a modified half-tongue test revealed recognition thresholds ranging from 3.0 to 1150.2 nmol/cm<sup>2</sup> for pungency and from 520.6 to 2162.1 nmol/cm<sup>2</sup> for the tingling orosensation depending on their chemical structure.