NMR-Based Studies on Odorant-Melanoidin Interactions in Coffee Beverages

J Agric Food Chem. 2021 Dec 22;69(50):15334-15344. doi: 10.1021/acs.jafc.1c06163. Epub 2021 Dec 7.


A quantitative 1H NMR-based approach was established, which allowed the direct and noninvasive analysis of molecular interactions between key coffee odorants and high-molecular-weight (HMW) melanoidin polymers. A clear distinction between covalent and noncovalent interactions was achieved by monitoring the time dependency of odorant-polymer interactions, resulting in four scenarios: covalent, π-π, covalent and π-π-, as well as no interactions. Evaluation of temperature influence on e.g. 2-furfurylthiol (FFT), revealed an altered behavior with increased π-π stacking at lower temperatures and accelerated covalent interactions at higher temperatures. Human sensory experiments with HMW material and a coffee aroma reconstitution model showed a drastic reduction of "roasty/sulfury" aroma notes, as well as an increased "sweetish/caramel-like" flavor. The lack of interactions between the "sweetish/caramel" smelling 4-hydroxy-2,5-dimethyl-3(2H)-furanone with the HMW melanoidins in combination with the high binding affinity of coffee thiols explains the sensory evaluation and is obviously the reason for the fast disappearance of the typical "roasty/sulfury" aroma impressions of a freshly prepared coffee brew.

Keywords: aroma binding; coffee beverages; covalent aroma binding; melanoidins; noncovalent π−π interactions; qHNMR; quantitative NMR spectroscopy.

MeSH terms

  • Beverages / analysis
  • Coffee*
  • Humans
  • Odorants* / analysis
  • Polymers


  • Coffee
  • Polymers
  • melanoidin polymers