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

de la Calle Arregui, Celia and Purdie, Jonathan A. and Haslam, Catherine A. and Law, Robert V. and Sanderson, John M. (2015) 'Optimised conditions for the synthesis of 17O and 18O labelled cholesterol.', Chemistry and physics of lipids., 195 . pp. 58-62.


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.

Item Type:Article
Keywords:Cholesterol, Synthesis, Oxygen isotope.
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Available under License - Creative Commons Attribution.
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Publisher statement:© 2016 The Authors. Published by Elsevier Ireland Ltd. This is an open access article under the CC BY license (
Date accepted:17 December 2015
Date deposited:03 February 2016
Date of first online publication:24 December 2015
Date first made open access:No date available

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