New Degradation Pathways of the Key Aroma Compound 1-Penten-3-one during Storage of Not-from-Concentrate Orange Juice

J Agric Food Chem. 2018 Oct 24;66(42):11083-11091. doi: 10.1021/acs.jafc.8b04334. Epub 2018 Oct 12.

Abstract

1-Penten-3-one with its fresh and pungent smell at a very low odor threshold of 0.94 μg/L water has been characterized as impact aroma compound in many foods, such as grapefruit, orange juice, black tea, olive oil, or tomatoes. While its importance to the fresh sensation of unstored not-from-concentrate (NFC) orange juice was recently confirmed by aroma recombinates, a total loss was determined already after 4 weeks in NFC orange juice stored at 0 °C. Until now, the degradation pathway of this compound has not been clarified. Systematic model studies resulted in the identification of 1-hydroxy-3-pentanone and 4-hydroxy-3,8-decanedione as degradation products as well as S-(3-oxopentyl)-l-cysteine in the presence of the amino acid. In orange juice samples, it was found that the elevated content of 1-hydroxy-3-pentanone indicates a thermal processing, while S-(3-oxopentyl)-l-cysteine showed a significant increase during cold storage. Additionally, both compounds were identified in other food samples, such as commercial orange juices, pickled olives and olive oil, fresh tomatoes and commercial tomato juice, and black tea.

Keywords: 1-hydroxy-3-pentanone; 1-penten-3-one; S-(3-oxopentyl)-l-cysteine; black tea; degradation products; ethyl vinyl ketone; olive oil; tomato juice.

MeSH terms

  • Citrus sinensis / chemistry*
  • Cysteine / chemistry
  • Food Handling / methods
  • Food Storage
  • Fruit and Vegetable Juices / analysis*
  • Molecular Structure
  • Odorants / analysis*
  • Olive Oil / chemistry
  • Pentanones / chemistry*
  • Tea / chemistry
  • Temperature

Substances

  • Olive Oil
  • Pentanones
  • Tea
  • Cysteine
  • 1-pentene-3-one