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

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.

Name thesis:degree_name

M.Sc. Chemistry

Level thesis:degree_level

Masters

Discipline thesis:degree_discipline

Faculty of Mathematics and Science

Department dc:contributor.department

Department of Chemistry

Grantor

Brock University

Year dc:date.issued

2017

Author dc:creator

• Hildering, Andrew

• Vitamin E
• Tocopherol
• Fluorescence

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/10464/10864

OAI identifier oai:identifier

oai:brocku.scholaris.ca:10464/10864