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Determination of the Enantiomeric Purity of Mevalonolactone via NMR Using a Chiral Lanthanide Shift Reagent

Determination of the Enantiomeric Purity of Mevalonolactone via NMR Using a Chiral Lanthanide Shift Reagent

W K Wilson, T J Scallen, C U Morrow

J Lipid Res. 1982 May;23(4):645-52.

PMID: 7097129

Abstract:

Simple methods for determining the enantiomeric purity of mevalonolactone and linalool by NMR using the chiral shift reagent Eu(hfc)3 are reported. These methods are more reliable than polarimetry and require only a few milligrams of sample to detect as little as 2% of the minor enantiomer. The accuracy of these methods is limited primarily by spectral resolution for samples of high enantiomeric excess and by errors inherent in measuring peak intensities for samples of low enantiomeric excess. The Cornforth synthesis (Cornforth, R. M., J. W. Cornforth, and G. Popják. 1962. Tetrahedron. 18: 1351-1354) of (S)-mevalonolactone from (R)-linalool has been improved and shown to proceed with negligible racemization.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP19115492	(R)-(−)-Mevalonolactone		19115-49-2	Price

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