Isolation and Derivatization of Sucralose from an Artificial Sweetener to Provide a Hands-On Laboratory Experiment Emphasizing Synthesis and Purification

Abstract

A laboratory experiment is detailed that entails the separation and derivatization of the artificial sweetener sucralose from a commercially available sweetener mixture. The experiment utilizes 1 g packets of a sucralose-based artificial sweetener and involves the separation of the synthetic sweetener from the more polar bulk additives by differential solubility. The semipure trichlorosucrose is then acetylated with acetic anhydride and purified using extraction and mini-column chromatography. The isolation, extraction, and chromatography can be followed by thin-layer chromatography in conjunction with 1H and 13C NMR spectroscopy for ascertaining purity during the process as well as final structural confirmation. The experiment is designed to utilize two 4 h laboratory periods, including any spectral work, and employs the laboratory apparatuses found in most undergraduate organic laboratories. During the experiment, the students learn separation by solubility, filtration, extraction, thin-layer and column chromatography, and acetylation of a carbohydrate to make a characterizable derivative. The usefulness of obtaining 1H and 13C NMR spectra as applied to structural analysis of carbohydrates and their derivatives is demonstrated.

“Bitter” Results: Toward Sustainable Synthesis of the Most Bitter Substances, Denatonium Saccharinate and Denatonium Benzoate, Starting from a Popular Anesthetic, Lidocaine

“…The most widely used salt of denatonium is benzoate, which is mainly applied as a bitterant to prevent inappropriate ingestion as well as a popular repellent in forestry . It should be noted that the safety of its use has been confirmed by both the U.S. Consumer Product Safety Commission as well as the European Food Safety Authority (EFSA). , Interestingly, its derivative consisting of a saccharinate anion, known as the second most used artificial sweetener in the United States and the same denatonium cation is 2 times more bitter and 2 times less toxic than the above-mentioned denatonium benzoate. , The structures of the most common denatonium salts with their bitterness and toxicity are provided in Table . Except for denatonium-based compounds, there are other substances that have been recognized for exhibiting a bitter taste, such as quercetin, brucine, quassin, or sucrose octaacetate. − Interestingly, 115 billion liters of bioethanol were produced worldwide for energy purposes in 2019, which consumes 1,150 tons of denatonium benzoate for denaturation…”

“…13 It should be noted that the safety of its use has been confirmed by both the U.S. Consumer Product Safety Commission as well as the European Food Safety Authority (EFSA). 13,14 Interestingly, its derivative consisting of a saccharinate anion, known as the second most used artificial sweetener in the United States 15 and the same denatonium cation is 2 times more bitter and 2 times less toxic than the above-mentioned denatonium benzoate. 14,16 The structures of the most common denatonium salts with their bitterness and toxicity are provided in Table 1.…”

Quinone Synthesis and a Visual Introduction to Column Chromatography: An Undergraduate Experiment

“…However, this technique is still commonly used in research laboratories as a purification process and so is, therefore, generally taught in the undergraduate (UG) chemistry laboratory curriculum. There have been several publications describing visual, colorful banded columns for an introduction to column chromatography, − and there have been publications involving column chromatography and synthesis; − however, there are currently no publications combining both a simple synthesis and visually indicative column chromatography separation. Here, we describe an undergraduate experiment which combines the context of a simple organic synthesis of a quinone derivative (quinones are known for being highly colored), and subsequent purification using a simple example of column chromatography, which features the important colorful bands needed for a visually accessible, first introduction to this challenging but important technique.…”

Separation and Analysis of Ginsenoside Rg1: An Experiment for the Separation and Analysis of Natural Products

“…Due to their extensive applicability in separating and analyzing active components from natural products, silica gel column chromatography (SGCC), thin layer chromatography (TLC), and high-performance liquid chromatography (HPLC) are the techniques with which undergraduate students studying pharmaceutical engineering should be acquainted. Several reports on these techniques incorporated into undergraduate teaching laboratories have been published in this Journal . − These reports focused mainly on the students’ mastery of these techniques, which was the training of experimental skills, − such as to separate an unknown mixture consisting of two colorless solids, a mixture of vivid colored components, ,, or a specific active ingredient in a natural product, ,,, to help students become familiar with the operation of column chromatography (CC) or to optimize the separation process of CC to help students understand the separation principle of CC in-depth. ,, Only a few reports focused on the overall knowledge structure formed by connecting the fragmented knowledge or skills in teaching. − Fragmented learning is only learning certain knowledge units. Its drawbacks are obvious, such as the fact that the links between the various fragmented knowledge units are scattered and the lack of a mutual logical relationship.…”