The Synthesis of α-Tocopentaenol (αT5), a Fluorescent Analogue of α-Tocopherol

Abstract

This thesis is focused on the investigation of synthesizing a fluorescent analogue of vitamin E, α-tocopentaenol (αT5). α-Tocopentaenol contains five conjugated double bonds across the phytyl tail, resulting in its fluorescence characteristics. Different methodologies of preparation were attempted to synthesize an all trans-configuration in the five-conjugated double bonds. Unfortunately, across the C3’ bond on the tail, geometric isomers were obtained. However, TBSO-αT5 was produced in what appeared to be ≈ 2:1 E:Z mixture across the C3’ bond (having the four other olefins with trans-configurations). α-Tocopentaenol showed a strong absorbance in ethanol with a maximum λab= 338 nm. This compound is stable as an oil, stored at -78˚C and protected from light for over a month with minimal degradation. Because αT5 resembles the naturally occurring form of the vitamin E, this analogue will enhance our ability to study the biological activity of vitamin E and will create an easy method of monitoring its presence in solution and cells.