2-Aminoacetophenone formation through UV-C induced degradation of tryptophan in the presence of riboflavin in model wine: Role of oxygen and transition metals.

Food Chem

Weincampus Neustadt, Dienstleistungszentrum Ländlicher Raum (DLR) Rheinpfalz, Breitenweg 71, 67435 Neustadt a. d. Weinstraße, Germany. Electronic address:

Published: November 2024

AI Article Synopsis

  • The study examines how light exposure, specifically from a UV-C source, affects the formation of 2-aminoacetophenone from tryptophan in wine, influenced by oxygen levels and transition metals.
  • More light exposure and higher oxygen concentrations led to increased levels of 2-aminoacetophenone, while transition metals slowed its formation and indicated a competing reaction involving acetaldehyde.
  • The research highlights the importance of oxygen, not only in the degradation of riboflavin but also in enhancing the light-induced formation of 2-aminoacetophenone, providing new insights into riboflavin's role in these reactions.

Article Abstract

2-Aminoacetophenone is an off-flavor that can result from tryptophan degradation via riboflavin-photosensitized reaction. This study investigates the impact of light exposure, provided by a UV-C source, oxygen concentrations and transition metals on the formation of 2-aminoacetophenone in model wine containing tryptophan and riboflavin. Irrespective of oxygen and transition metals, >85% of tryptophan were degraded via first-order kinetics to unknown product(s). However, longer light exposure and more oxygen caused 2-aminoacetophenone concentrations to increase. Transition metals decelerated the 2-aminoacetophenone formation and acetaldehyde was formed suggesting photo-Fenton reaction occurred as a competitive reaction. The degradation rate of riboflavin inclined with less oxygen and in the presence of transition metals due to the depletion of oxygen by photo-Fenton reaction. Oxygen plays an important role in the regeneration of riboflavin and therefore must be seen as an intensifier for light-induced 2-aminoacetophenone formation. This paper provides new insights into riboflavin-photosensitized reactions.

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Source
http://dx.doi.org/10.1016/j.foodchem.2024.140259DOI Listing

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