Evidence in the formation of conjugated linoleic acids from thermally induced 9t12t linoleic acid: a study by gas chromatography and infrared spectroscopy

Chem Phys Lipids. 2009 Oct;161(2):86-94. doi: 10.1016/j.chemphyslip.2009.07.002. Epub 2009 Jul 17.

Abstract

Thermally induced isomerisation leading to the formation of conjugated linoleic acids (CLAs) has been observed for the first time during the thermal treatment of 9t12t fatty acid triacylglycerol, and methyl ester. Fifteen microlitre portions of the triacylglycerol sample containing 9t12t fatty acid (trilinoelaidin) were placed in micro glass ampoules and sealed under nitrogen, then subjected to thermal treatment at 250 degrees C. The glass ampoules were removed at regular time intervals, cut open, and the contents were analysed by infrared spectroscopy using a single reflectance attenuated total internal reflectance crystal accessory. The samples were then subjected to derivatisation into their methyl esters. The methyl esters of the isomerised fatty acids were analysed by gas chromatography. The same procedure was repeated with methyl ester samples containing 9t12t fatty acid (methyl linoelaidate). Each sample was subjected to infrared measurements and gas chromatographic analysis after appropriate dilution in heptane. The results show that the thermally induced isomerisation of 9t12t fatty acids from both triacylglycerol molecules and methyl esters give identical CLA profiles as those found for the thermally induced isomerisation of 9c12c fatty acids. The infrared spectrometry provides additional evidence confirming the formation of CLA acids during thermal treatment. A mechanism for the formation of the CLAs from 9t12t fatty acid molecules is also formulated for the first time. This mechanism complements the pathways of formation of CLAs from 9c12c fatty acids during thermal treatment.

MeSH terms

  • Chromatography, Gas / methods*
  • Dietary Fats / metabolism
  • Fatty Acids / analysis
  • Fatty Acids, Omega-3 / chemistry
  • Fermentation
  • Linoleic Acids, Conjugated / chemistry*
  • Spectrophotometry, Infrared / methods*
  • Triglycerides / chemistry

Substances

  • Dietary Fats
  • Fatty Acids
  • Fatty Acids, Omega-3
  • Linoleic Acids, Conjugated
  • Triglycerides
  • trilinolein