Optimised conditions for the synthesis of 17O and 18O labelled cholesterol

de la Calle Arregui, Celia; Purdie, Jonathan A.; Haslam, Catherine A.; Law, Robert V.; Sanderson, John M.

Abstract

Conditions are described for the preparation of cholesterol with 17O and 18O labels from i-cholesteryl methyl ether using minimal amounts of isotopically enriched water. Optimum yields employed trifluoromethanesulfonic acid as catalyst in 1,4-dioxane at room temperature with 5 equivalents of water. An isotopic enrichment >90% of that of the water used for the reaction could be attained. Tetrafluoroboric acid could also be used as catalyst, at the expense of a lower overall reaction yield. Byproducts from the reaction included dicholesteryl ether, methyl cholesteryl ether, compounds formed by ether hydrolysis, and olefins arising from elimination reactions. Reactions in tetrahydrofuran yielded significant amounts of cholesteryl ethers formed by reaction with alcohols arising from hydrolysis of the solvent.

Citation

de la Calle Arregui, C., Purdie, J. A., Haslam, C. A., Law, R. V., & Sanderson, J. M. (2015). Optimised conditions for the synthesis of 17O and 18O labelled cholesterol. Chemistry and Physics of Lipids, 195, 58-62. https://doi.org/10.1016/j.chemphyslip.2015.12.003

• Journal Article Type: Article
• Acceptance Date: Dec 17, 2015
• Online Publication Date: Dec 24, 2015
• Publication Date: Feb 1, 2015
• Deposit Date: Dec 22, 2015
• Publicly Available Date: Feb 3, 2016
• Journal: Chemistry and Physics of Lipids
• Print ISSN: 0009-3084
• Electronic ISSN: 1873-2941
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 195
• Pages: 58-62
• DOI: https://doi.org/10.1016/j.chemphyslip.2015.12.003
• Keywords: Cholesterol, Synthesis, Oxygen isotope.
• Public URL: https://durham-repository.worktribe.com/output/1424473