New synthesis of (±)-α-CMBHC and its confirmation as a metabolite of α-tocopherol (vitamin E) Original Research Article

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 α-tocopherol was identified, which we tentatively characterised as 5-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)-2-methyl-pentanoic acid (α-CMBHC).1 Here we describe the synthesis of α-CMBHC as a standard and confirm that it is a metabolite of α-tocopherol.