Analysis of the Formation of Sucralose Derivatives using GC-MS
Faculty Sponsor
Trisha Russell, Whitworth University
Research Project Abstract
Splenda contains sucralose (1,6-dichloro-1,6-dideoxy-b-D-fructofuranosyl-4-chloro-4-deoxy-a-D-galactopyran-oside) and is a common substitute sweetener for sucrose. Many studies have been completed testing sucralose for possible hazards and its biological importance because of its zero calorie and high-level sweetness. While generally regarded as safe, the chemistry of sucralose under basic conditions has not been established. This study monitored the reaction of sucralose in basic water under reflux. When sucralose is treated with a weak base and water, sucralose undergoes two cyclizations on the fructose ring. The goal was to evaluate which cyclization of the fructose occurred first. The reaction was monitored by collecting samples over time, converting them into volatile trimethylsilyl (TMS) ether derivatives, and analyzing the samples by GC-MS. As the reaction progressed the monocyclized derivative increased and then decreased, and the amount of the dicyclized derivative increased. The reaction proceeded to form the 1,4:3,6-dianhydro-β-D-fructofuranosyl-4-chloro-4-deoxy-α-D-galacopyranoside (dicyclized product). The monocyclized product (3,6-anhydro-1-chloro-1-deoxy-β-D-fructofuranosyl-4-chloro-4-deoxy-α-D-galacopyranoside) was identified as the intermediate in the reaction.
Session Number
PS1
Location
Graves Gym
Abstract Number
PS1-z
Analysis of the Formation of Sucralose Derivatives using GC-MS
Graves Gym
Splenda contains sucralose (1,6-dichloro-1,6-dideoxy-b-D-fructofuranosyl-4-chloro-4-deoxy-a-D-galactopyran-oside) and is a common substitute sweetener for sucrose. Many studies have been completed testing sucralose for possible hazards and its biological importance because of its zero calorie and high-level sweetness. While generally regarded as safe, the chemistry of sucralose under basic conditions has not been established. This study monitored the reaction of sucralose in basic water under reflux. When sucralose is treated with a weak base and water, sucralose undergoes two cyclizations on the fructose ring. The goal was to evaluate which cyclization of the fructose occurred first. The reaction was monitored by collecting samples over time, converting them into volatile trimethylsilyl (TMS) ether derivatives, and analyzing the samples by GC-MS. As the reaction progressed the monocyclized derivative increased and then decreased, and the amount of the dicyclized derivative increased. The reaction proceeded to form the 1,4:3,6-dianhydro-β-D-fructofuranosyl-4-chloro-4-deoxy-α-D-galacopyranoside (dicyclized product). The monocyclized product (3,6-anhydro-1-chloro-1-deoxy-β-D-fructofuranosyl-4-chloro-4-deoxy-α-D-galacopyranoside) was identified as the intermediate in the reaction.
