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Assignment of the 1 H and 13 C NMR of tocotrienols
Author(s) -
Ohnmacht Stephan,
West Ryan,
Simionescu Razvan,
Atkinson Jeffrey
Publication year - 2008
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2176
Subject(s) - chemistry , degree of unsaturation , stereochemistry , side chain , two dimensional nuclear magnetic resonance spectroscopy , tocotrienol , nuclear magnetic resonance spectroscopy , heteronuclear single quantum coherence spectroscopy , tocopherol , vitamin e , organic chemistry , antioxidant , polymer
Vitamin E is a family of chromanols that vary by the degree of methylation of the chroman ring as well as the nature of the hydrophobic side chain at C2 that serves to anchor these lipids in biological membranes. The tocopherols contain saturated side chains, whereas the tocotrienols contain three sites of unsaturation and are derived from geranylgeranyl diphosphate. A growing interest in the unique biological activities of the tocotrienols has led us to begin syntheses of isotopically substituted forms and other derivatives that will be useful for probing the metabolism and membrane behavior of the tocotrienols. In order to be certain of our ability to selectively modify sites on the parent molecules it was necessary to make as complete an assignment of the 1 H and 13 C NMR as possible. Herein we report multidimensional NMR data (HSQC, COSY, ADEQUATE(1,1), CH HMBC, and NOESY) that have allowed us to assign the identity of almost all the resonances for α‐, β‐, γ‐, and δ‐tocotrienol. Copyright © 2008 John Wiley & Sons, Ltd.