Thermal oxidation of cholesterol: Preliminary evaluation of 2-methyl-6-heptanone and 3-methylbutanal as volatile oxidation markers

Steroids. 2015 Jul;99(Pt B):161-71. doi: 10.1016/j.steroids.2015.03.017. Epub 2015 Apr 3.

Abstract

Cholesterol oxidation in food and model systems is usually monitored by evaluating cholesterol oxidation products, but the analysis is time-consuming and expensive. Therefore, the determination of volatile compounds deriving from cholesterol thermoxidation could be valuable to identify other possible oxidation markers. Cholesterol alone and in the presence of a triacylglycerol mixture (tripalmitin, tristearin, and triolein) were thermoxidized at 170°C for 15min. In both model systems, the total volatile compounds increased three times when oxidation time rose from 5 to 15min. The main classes of volatile compounds were aldehydes, ketones, alcohols and hydrocarbons, displaying a similar behavior in both systems. After 5min of oxidation, 2-methyl-6-heptanone was the main volatile compound, followed by 3-methylpentane, 2,3-dimethyl-1-pentene and 3-methylbutanal. To verify if 2-methyl-6-heptanone could be used as volatile marker of cholesterol oxidation, data were compared with the total cholesterol oxidation products content of each system. A significant correlation between total cholesterol oxidation products content and 2-methyl-6-heptanone amount was found when cholesterol was oxidized alone (r(2)=0.994) and in presence of triacylglycerols (r(2)=0.998). When egg yolk was thermoxidized at 80°C for 6h, 3-methylbutanal was the volatile compound that better explained the oxidative trend in this food system, showing a significant correlation with cholesterol oxidation rate (r=0.91). In conclusion, 2-methyl-6-heptanone and 3-methylbutanal could represent an easy and cheaper strategy for monitoring cholesterol oxidation in model systems and food samples, respectively; however, a deeper investigation on the amount and type of volatile compounds generated from cholesterol oxidation according to the food matrix, should be carried out.

Keywords: Cholesterol oxidation; Egg yolk; Model systems; Thermoxidation; Triacylglycerols; Volatile compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Animals
  • Chickens
  • Cholesterol / chemistry*
  • Egg Yolk / chemistry
  • Ketones / chemistry*
  • Oxidation-Reduction
  • Principal Component Analysis
  • Temperature*
  • Triglycerides / analysis
  • Volatile Organic Compounds / analysis
  • Volatilization

Substances

  • Aldehydes
  • Ketones
  • Triglycerides
  • Volatile Organic Compounds
  • isovalerylaldehyde
  • Cholesterol
  • 6-methyl-2-heptanone