Abstract:
Since its discovery in 1922, vitamin E has been widely investigated for its role as a
powerful, chain-breaking antioxidant that is required for human health. However, some
basic issues still remain unclear, such as the mechanism and dynamics of the intracellular
trafficking of a-tocopherol. To better understand tocopherol's biological activity at the
cellular level, fluorescence spectroscopy and microscopy have been found to be valuable
tools.
This thesis reports the synthesis of a new fluorescent analogue of a-tocopherol, atocohexaenol,
an intrinsically fluorescent analogue of a-tocopherol. Different
methodologies of preparation have been attempted and a strategy using a preformed
chromanol head plus ClO and Cs portion of the polyene side chain finally provided us the
desired a-tocohexaenol. a-Tocohexaenol shows a strong fluorescence in both ethanol and
hexanes with maximum Aab = 368 nm and maximum /...em = 521 nm. This compound is
stable for a couple of weeks in ethanol or hexane solution if stored at 0 °C and protected
form light. It decomposes slowly at room temperature and light will accelerate its
decomposition (within 5 hours). Thus, a-Tocohexaenol may be a useful fluorescent probe
to study the biochemistry and cell biology of vitamin E.
