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7-Hydroperoxycholesterol is considered to be an intermediate compound of the cholesterol oxidation path as the first product formed when cholesterol is oxidized by triplet oxygen. However, there is a limitation on cholesterol mechanism studies because of the lack of 7-hydroperoxycholesterol analytical standard due to its low stability. To verify the formation of hydroperoxides in cholesterol model systems heated at 140, 180, and 220 °C, 7α-hydroperoxycholesterol was synthesized by cholesterol photooxidation followed by rearrangement at room temperature in chloroform. Its structure was confirmed on the basis of 13C NMR and mass spectra obtained by APCI-LC-MS. The synthesized compound was also used as standard for the quantification of 7-hydroperoxycholesterol as the sum of 7α- and 7β-hydroperoxycholesterol. The results demonstrated that 7-hydroperoxycholesterol is the first compound formed when the temperature is lower (140 °C). However, the concentration of the 7-hydroperoxycholesterol depends on the temp...
| Authors: | Gislaine C. Nogueira; Bruna Z. Costa; Antonio E. M. Crotti; Neura Bragagnolo; Gislaine C. Nogueira; Bruna Z. Costa; Antonio E. M. Crotti | |
| Journal: | Journal of Agricultural and Food Chemistry | |
| Year: | 2010 | |
| DOI: | 10.1021/jf102252r | |
| Publication date: | 15-09-2010 |
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