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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.

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Authors

Celia de la Calle Arregui

Jonathan A. Purdie

Catherine A. Haslam

Robert V. Law



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 Mar 28, 2024
Journal Chemistry and Physics of Lipids
Print ISSN 0009-3084
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.

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