New synthesis of (+/-)-alpha-CMBHC and its confirmation as a metabolite of alpha-tocopherol (vitamin E)

  • Bioorg Med Chem. 2001 May;9(5):1337-43. doi: 10.1016/s0968-0896(01)00010-4.
S A Pope  1 ,  G E Burtin ,  P T Clayton ,  D J Madge ,  D P Muller
Affiliations
  • 1. Biochemistry, Endocrinology and Metabolism Unit, The Institute of Child Health, University College London, London WC1N 1EH, UK.
PMID: 11377190 DOI: 10.1016/s0968-0896(01)00010-4
Abstract

There is currently interest in the metabolism of the various compounds which make up the vitamin E family, especially with regards to the possible use of vitamin E metabolites as markers of oxidative stress and adequate vitamin E supply. A number of vitamin E metabolites have been described to date and we have recently developed a method to extract and quantitate a range of vitamin E metabolites in human urine. During the development of this method a new metabolite of alpha-tocopherol was identified, which we tentatively characterised as 5-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)-2-methyl-pentanoic acid (alpha-CMBHC).(1) Here we describe the synthesis of alpha-CMBHC as a standard and confirm that it is a metabolite of alpha-tocopherol.

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