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Synthesis of [1,3,5-13C3]benzoic acid and [2,4,6,7-13C4]benzoic acid from 13C-labelled sodium pyruvates

✍ Scribed by Kazuki Akira; Shigeo Baba

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
417 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of [1,3,5‐^13^C~3~]‐ and [2,4,6,7‐^13^C~4~]benzoic acid (5a and 5b) from [2‐^13^C]‐ and [3‐^13^C]sodium pyruvate (1a and 1b), for in vitro and in vivo tracer studies using ^13^C nuclear magnetic resonance (NMR) spectroscopy, is reported. After condensation of 1 to [^13^C]methyldihydrotrimesic acids 2 using sodium hydroxide, decarboxylation to [^13^C]uvitic acid 3 was carried out using conc. sulfuric acid. Additional decarboxylation of 3 was achieved with cupric oxide and quinoline, and the resulting [^13^C]toluenes 4 were effectively trapped, using a simplified decarboxylation apparatus. Compounds 4 were subsequently oxidized to 5 using potassium permanganate without further purification. The overall yields of 5 from 1 were 26–28 %, with isotopic purities of 96–98 %. In addition, the assignments for ^13^C NMR signals of benzoic acid were first substantiated.

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