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Updated: Jun 19, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
A non-fluorescent derivative from derivatizing trans, trans-muconic acid with
Tang-Chia Chung1, Wung-Pung Su, Hwang-Shang Kou
1Graduate Institute of Pharmaceutical Sciences, Collage of Pharmacy, Kaohsiung Medical University, Kaohsiung, 807, Taiwan.
Abstract:
trans, trans-Muconic acid (MA) is a polar metabolite of benzene and used as a biomarker for monitoring human exposure to benzene. Because MA is a trace metabolite, sensitive method is required for its detection. In addition, MA is a highly polar compound with dicarboxyl functions that could incur unfavorable adsorption on silica-based stationary phase usually used for separation. To address these problems, we planned to derivatize MA with a fluorescent reagent 2-(2-naphthoxy)ethyl-2-(piperidino)ethanesulfonate to give a naphthoxy derivative of MA for improving detection sensitivity and chromatographic properties. Surprisingly, the resulting derivative shows no fluorescent activity (lambda(ex): 226 nm; lambda(em): 350 nm). The negative results could be used as an instructive example for discussing on fluorescence quenching.
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