PMID: 11312861Apr 21, 2001Paper

Characterization of natural "cooling" compounds formed from glucose and l-proline in dark malt by application of taste dilution analysis

Journal of Agricultural and Food Chemistry
Harald OttingerThomas Hofmann

Abstract

Gel permeation chromatography of the solvent extractables isolated from a thermally treated glucose/L-proline mixture and sensory analysis of the fractions collected led to the discovery of the presence of "cooling" compounds in Maillard reactions. To characterize the key compounds imparting this cooling sensation to the oral cavity, a taste dilution analysis was performed by determining the taste threshold of reaction products in serial dilutions of HPLC fractions to select the most intense "cooling" compounds in the complex GPC fraction of the Maillard reaction mixture. Systematic (13)C-labeling experiments and GC-MS, LC-MS, and 1D- and 2D-NMR measurements, followed by synthesis, led to the unequivocal identification of 3-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (3-MPC), 5-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (5-MPC), and 2,5-dimethyl-4-(1-pyrrolidinyl)-3(2H)-furanone (DMPF) as the key compounds contributing the most to the cooling sensation. Although these structures were described earlier with regard to Maillard reactions, this is the first time that Maillard reaction products are reported to cause intense cooling sensations by degustation. Finally, the detection of 5-MPC (101.3 microg/kg), 3-MPC (9.4 microg/k...Continue Reading

Citations

Aug 4, 2012·ACS Chemical Neuroscience·Sonali S Bharate, Sandip B Bharate
Feb 23, 2012·Journal of Agricultural and Food Chemistry·Corinna DawidThomas Hofmann
Nov 10, 2012·Journal of Agricultural and Food Chemistry·Corinna Dawid, Thomas Hofmann
Jul 23, 2005·Annals of the New York Academy of Sciences·Thomas Hofmann
Oct 22, 2004·Molecular Nutrition & Food Research·Tomislav SoldoThomas Hofmann
May 20, 2017·Journal of Agricultural and Food Chemistry·Ian RonningenDevin G Peterson
Feb 1, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maximilian Kranz, Thomas Hofmann
Dec 22, 2005·Emotion·Stefan G HofmannDiego A Pizzagalli
Mar 22, 2008·Journal of Agricultural and Food Chemistry·Simone Toelstede, Thomas Hofmann
Mar 21, 2009·Journal of Agricultural and Food Chemistry·Bernd Schwarz, Thomas Hofmann
Nov 18, 2010·Journal of Agricultural and Food Chemistry·Andreas Georg Degenhardt, Thomas Hofmann
Dec 20, 2017·Journal of Agricultural and Food Chemistry·Ian G Ronningen, Devin G Peterson
Dec 18, 2010·Journal of Agricultural and Food Chemistry·Daniel Festring, Thomas Hofmann
Jan 16, 2008·Journal of Agricultural and Food Chemistry·Jan Carlos Hufnagel, Thomas Hofmann
Sep 27, 2008·Journal of Agricultural and Food Chemistry·Oliver FrankThomas Hofmann

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