Synthesis of 3-methyl-15-phenyl-[carboxyl-14C]-pentadecanoic acid

✍ Scribed by T. Humbert; C. Luu-Duc; D. Le Bars; M. Vidal; M. Apparu

• Publisher: John Wiley and Sons
• Year: 1988
• Tongue: French
• Weight: 241 KB
• Volume: 25
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580250919

✦ Synopsis

with good yield in t w o steps f r o m Na14CN, starting from 14-methyl 1-phenyl-tetradecanol methanesulfonate with a specific radioactivity : 108.25 pCi/mg, 1.92 mCilmmo1. and in a radiochemical yield of 50% of the theoretical amount.

p-Methyl-15-phenyl-pentadecanoic acid labelled with carbon-14 was obtained

INTRODUCTION :

In order to investigate the mymardic metabolism of fatty acids, 3-methyl-15-phenyl-[~arboxyl-~~C]pentadecanoic acid (MPPA) has been synthesized in good yield from [ 14C]NaCN. In the mitochondria, the P-oxydation of this fatty acid is stopped by the P-methyl side chain and this allows a longer experimental time in animal study (1-3). The labelled compound 6 was obtained by an original synthesis according to the Scheme 1 (4-9). This most suitable method allowed a reduced cyanide ratio (only 1.3 equivalent w i t h regard to the mesylate compound s> without yield falling followed by a simple purification of the[l4C1nitrile 1 after the nucleoplilic substitution reaction (10). 0362 -4803/88/091W9-O6SOS.OO 0 1988 by John W k y & Sons, Ltd.