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  • Identification of (furan-2-yl)methylated benzene diols and triols as a novel class of bitter compounds in roasted coffee
  • Add time:08/08/2019         Source:sciencedirect.com

    Preliminary studies demonstrated that the identification of unknown bitter taste compounds in roasted coffee, by means of an analytical fractionation approach, is hampered by their limited oxidative, as well as chemical stability. A synthetic-constructive strategy was followed in the present investigation by performing targeted reactions of putative coffee-related precursors to give candidate bitter taste molecules. Binary mixtures of a di and trihydroxybenzene, namely pyrogallol, hydroxyhydroquinone, catechol, or 3- and 4-methylcatechole, and a furan derivative, namely furfuryl alcohol, furan-2-aldehyde, or 5-(hydroxymethyl)furan-2-aldehyde, all of which are known to be present in roasted coffee, were thermally treated. The reaction products were identified as (furan-2-yl)methylated benzene diols and triols, by means of LC–MS and NMR experiments, and their bitter taste thresholds determined by means of sensory analysis. Finally, LC–MS/MS studies verified the natural occurence of 4-(furan-2-ylmethyl)benzene-1,2-diol, 4-(furan-2-ylmethyl)benzene-1,2,3-triol, 4-(furan-2-ylmethyl)-5-methylbenzene-1,2-diol, and 3-(furan-2-ylmethyl)-6-methylbenzene-1,2-diol as a novel class of bitter taste compounds in roasted coffee. Depending on their chemical structure, the bitter taste recognition threshold of these compounds ranged between 100 and 537 μmol/l.

    ► Hydroxybenzenes react with furanaldehydes to form (furan-2-yl)methylated benzenes. ► (Furan-2-yl)methylated benzenes are formed upon coffee roasting. ► (Furan-2-yl)methylated benzenes exhibit potent bitter taste. ► Formation of (furan-2-yl)methylated benzenes runs via the furfuryl cation.

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    Prev:Synthesis, crystal structure investigation, DFT studies and DPPH radical scavenging activity of 1-(furan-2-ylmethyl)-2,4,5-triphenyl-1H-imidazole derivatives
    Next: Transition-metal-free insertion of benzyl bromides into 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde: One-pot switchable syntheses of benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones and 3-arylquinolin-4-ones mediated by base)

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