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Further oxidation products of 2,2,5,7,8-pentamethyl-6-chromanol

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Lipids

Abstract

In order to undertake a quantitative study by high-performance liquid chromatography of the rate of oxidation of 2,2,5,7,8-pentamethyl-6-chromanol (1), the model compound of α-tocopherol, a number of potential products were required as standards. Among these compounds were 2,2,7,8-tetramethylchroman-5,6-dione (10) and 2,2,7-trimethyl-6-hydroxychroman-5,8-dione (17), the model compounds of tocored and tocopurple, respectively. Attempts to synthesize 10 and 17 led to the isolation of 8-hydroxymethyl-2,2,7-trimethylchroman-5,6-dione (14) and 1,2-bis(2,2,7-trimethylchroman-5,6-dione-8-)ethane (19) a dimer of 10. Purification by thin-layer chromatography of the spirodimer (20) of 1 resulted in an acid-catalyzed decomposition to 1-(2,2,7,8-tetramethyl-6-chromanol-5-)2-[2-(3-methyl-3-hydroxybutyl)-5,6-dimethyl-1,4-benzoquinone-3-]ethane (23), a new chromanol-quinone dimer.

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Abbreviations

E.I.:

electron impact

Fo :

observed structure amplitude

HPLC:

high-performance liquid chromatography

IR:

infrared

Io :

observed intensity

MS:

mass spectrum

NMR:

nuclear magnetic resonance

σ:

standard deviation

θ:

diffraction angle

TLC:

thin-layer chromatography

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Authors and Affiliations

  1. Department of Organic Chemistry, University of New South Wales, P.O. Box 1, 2033, Kensington, N.S.W., Australia

    Cacang Suarna, Manuel Baca, Donald C. Craig, Marcia Scudder & Peter T. Southwell-Keely

Authors
  1. Cacang Suarna
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  2. Manuel Baca
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  3. Donald C. Craig
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  4. Marcia Scudder
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  5. Peter T. Southwell-Keely
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Suarna, C., Baca, M., Craig, D.C. et al. Further oxidation products of 2,2,5,7,8-pentamethyl-6-chromanol. Lipids 26, 847–852 (1991). https://doi.org/10.1007/BF02536168

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  • DOI: https://doi.org/10.1007/BF02536168

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