{"id":{"repo_id":"brock","oai_identifier":"oai:brocku.scholaris.ca:10464/10864"},"canonical_url":"https://search.dev.ndltd.org/etd/brock/oai:brocku.scholaris.ca:10464/10864","repository":{"repo_id":"brock","name":"Brock University","base_url":"https://brocku.scholaris.ca/server/oai/request"},"display":{"title":"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.","abstract_html":"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.","abstract_has_math":false,"creators":["Hildering, Andrew"],"institution":"Brock University","degree_name":"M.Sc. Chemistry","degree_level":"Masters","degree_discipline":"Faculty of Mathematics and Science","degree_department":"Department of Chemistry","school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2017,"date_issued":"2017-01-09T16:54:39Z","date_published":"2017-01-09T16:54:39Z","updated_at":"2026-07-24T01:23:18Z","subjects":["Vitamin E","Tocopherol","Fluorescence"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/10464/10864","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.department","label":"Department","values":["Department of Chemistry"]},{"key":"dc:creator","label":"Author","values":["Hildering, Andrew"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2017-01-09T16:54:39Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2017-01-09T16:54:39Z"]},{"key":"dc:date.issued","label":"Date","values":["2017-01-09T16:54:39Z"]},{"key":"dc:type","label":"Dc Type","values":["Electronic Thesis or Dissertation"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Faculty of Mathematics and Science"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Masters"]},{"key":"thesis:degree_name","label":"Degree Name","values":["M.Sc. 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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."]},{"key":"dc:title","label":"Title","values":["The Synthesis of α-Tocopentaenol (αT5), a Fluorescent Analogue of α-Tocopherol"]}]}],"canonical_facts":{"dc:contributor.department":["Department of Chemistry"],"dc:creator":["Hildering, Andrew"],"dc:date.accessioned":["2017-01-09T16:54:39Z"],"dc:date.available":["2017-01-09T16:54:39Z"],"dc:date.issued":["2017-01-09T16:54:39Z"],"dc:description.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."],"dc:identifier.uri":["http://hdl.handle.net/10464/10864"],"dc:language.iso":["eng"],"dc:subject":["Vitamin E","Tocopherol","Fluorescence"],"dc:title":["The Synthesis of α-Tocopentaenol (αT5), a Fluorescent Analogue of α-Tocopherol"],"dc:type":["Electronic Thesis or Dissertation"],"thesis:degree_discipline":["Faculty of Mathematics and Science"],"thesis:degree_level":["Masters"],"thesis:degree_name":["M.Sc. Chemistry"],"thesis:institution_name":["Brock University"]},"updated_at":"2026-07-24T01:23:18Z"}