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Optimised Conditions for the Synthesis of (17)O and (18)O Labelled Cholesterol

Optimised Conditions for the Synthesis of (17)O and (18)O Labelled Cholesterol

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

Chem Phys Lipids. 2016 Feb;195:58-62.

PMID: 26724708

Abstract:

Conditions are described for the preparation of cholesterol with (17)O and (18)O 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2867938	i-Cholesteryl methyl ether		2867-93-8	Price

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