Journal article

Oxidation of sterols: energetics of C–H and O–H bond cleavage

  • Lengyel, Jozef J. Heyrovský Institute of Physical Chemistry, Prague, Czech Republic - Department of Physical Chemistry, Institute of Chemical Technology, Prague, Czech Republic
  • Rimarčík, Ján Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Bratislava, Slovakia
  • Vagánek, Adam Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Bratislava, Slovakia
  • Fedor, Juraj Department of Chemistry, University of Fribourg, Switzerland
  • Lukeš, Vladimír Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Bratislava, Slovakia
  • Klein, Erik Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Bratislava, Slovakia
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    16.02.2012
Published in:
  • Food Chemistry. - 2012, vol. 133, no. 4, p. 1435–1440
English Phytosterols, as components of human diet, received much attention because of their cholesterol-lowering and antioxidant properties. We have theoretically studied sterols oxidation in terms of O–H and C–H bond dissociation enthalpies (BDE). In 17 Δ⁵- and Δ⁷-sterols, BDEs were obtained for reported sites of oxidation attack. Obtained results indicate that Δ⁷-sterols are more susceptible to oxidation attack in comparison to Δ⁵-sterols. In sterol nuclei, the lowest BDE was found for C7–H bond in Δ⁵-sterols and for C14–H in Δ⁷-sterols. When Δ⁵-sterol has a C=C double bond in the side chain, the lowest BDEs are usually found for C–H bonds in α-positions to this bond. The homolytic cleavage of hydroxyl O–H bond requires larger energy in comparison to the studied C–H bonds. We have shown that the C–H bonds with lowest BDE values actually correspond to the dominant sites of oxidation attack.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/unifr/documents/302404
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