Cycloartenol is a steroidal triterpenoid found naturally in olive oil. When cycloartenol is heated to above ~30oC, it has been shown to isomerize to a different product. We have investigated this isomerization process using quantum chemical calculations and found that the pathway features a 1,2-hydride shift proceeded by protonation of a carbon. Our calculations were performed at mPW1PW91/6-31+G(d,p). Transition state structures were located by scanning C-H bond distances and optimizing the maximum-energy points of these scans as transition states. This procedure makes locating transition state structures completely accessible to a visually impaired person. Models of the reactants and intermediates constructed by a 3D printer also allow a blind chemist to examine the structures without sighted assistance. Our results show the energy barrier to be approximately 3.4kcal/mol for the 1,2-hydride shift, suggesting that the process is energetically feasible at 35oC. Therefore, the presence of cycloartenol's isomerized product in olive oil is probably due to thermal processing of that oil. Computational and any experimental results for cycloartanol and its isomerized product if applicable will be discussed. Physical three-dimensional models of intermediates complete with Braille labels for reactants, intermediates, and products will be presented and methodologies using 3-D printouts to make computational organic chemistry accessible to the blind will be addressed.

Isomerization of cycloartanol: An indicator of thermally-treated olive oil

248th National Meeting (2014)

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