Effect of Furan Fatty Acids and 3-Methyl-2,4-nonanedione on Light-Induced Off-Odor in Soybean Oil

J Agric Food Chem. 2017 Mar 15;65(10):2136-2140. doi: 10.1021/acs.jafc.6b05056. Epub 2017 Feb 28.


Soybean oil is one of the most widely consumed vegetable oils. However, under photooxidative conditions, this oil develops a beany and green off-odor through a mechanism that has not yet been elucidated. Upon photooxidation, 3-methyl-2,4-nonanedione (3-MND) produces a strong aroma. In this study, the effect of furan fatty acids and 3-MND on odor reversion in soybean oil was investigated. Our findings suggest that the observed light-induced off-odor was likely attributable to the furan fatty acids present in the oil through the generation of 3-MND. While 3-MND may not be directly responsible for the development of light-induced off-odor, this compound appears to be involved because off-odor was detected in canola oil samples containing added 3-MND. In addition, in the present work, 3-hydroxy-3-methyl-2,4-nonanedione, which is derived from 3-MND, was identified for the first time in light-exposed soybean oil and shown to be one of the compounds responsible for odor reversion.

Keywords: 3-hydroxy-3-methyl-2,4-nonanedione; 3-methyl-2,4-nonanedione; furan fatty acids; light-induced off-odor; soybean oil.

MeSH terms

  • Alkanes / chemistry*
  • Diacetyl / analogs & derivatives*
  • Diacetyl / chemistry
  • Fatty Acids / chemistry*
  • Furans / chemistry*
  • Light
  • Odorants / analysis
  • Soybean Oil / chemistry*
  • Soybean Oil / radiation effects


  • Alkanes
  • Fatty Acids
  • Furans
  • Soybean Oil
  • 3-methyl-2,4-nonanedione
  • Diacetyl
  • furan