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First Synthesis of rac-(5-²H₃)-α-CEHC, a Labeled Analogue of a Major Vitamin E Metabolite

Francesco Mazzini,^† Thomas Netscher,^‡ and Piero Salvadori*^†

Dipartimento di Chimica e Chimica Industriale, Universit di Pisa, Via Risorgimento 35, 56126 Pisa, Italy psalva@dcci.unipi.it

J. Org. Chem., 2004, 69 (26), pp 9303–9306

DOI: 10.1021/jo048514u

Publication Date (Web): November 6, 2004

†

Dipartimento di Chimica e Chimica Industriale, Università di Pisa, 56126 Pisa, Italy.

‡

Research and Development, DSM Nutritional Products, P.O. Box 3255, CH-4002 Basel, Switzerland.

To whom correspondence should be addressed. Tel: +39 050 2219918273. Fax: +39 050 2219918260.

Abstract

Over the past few years, quantitative determination of α- and γ-CEHC, main urinary metabolites of vitamin E, has been becoming more and more important as a key parameter in assessing oxidative stress and supplementation of tocopherols. The use of deuterated analogues of these metabolites allows their accurate determination even in complex matrixes. While preparation of γ-CEHC-d₂ has already been described, here we report the first synthesis of α-CEHC-d₃ together with α-tocopheronolactone-d₃, its oxidation product.

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Published In Issue December 24, 2004
Received August 24, 2004

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Note

First Synthesis of rac-(5-²H₃)-α-CEHC, a Labeled Analogue of a Major Vitamin E Metabolite