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Synthesis of [18‐ 14 C]octatriacontane from [1‐ 14 C]stearic acid
Author(s) -
Hassam Saifunnissa B.
Publication year - 1987
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580240113
Subject(s) - chemistry , stearic acid , yield (engineering) , hydrolysis , specific activity , carbon 14 , nuclear chemistry , silica gel , organic chemistry , chromatography , radiochemistry , enzyme , materials science , metallurgy , physics , quantum mechanics
A method was developed to synthesize 14 C‐labelled n‐alkanes for use in cigarette smoke studies. Specifically, n‐[18‐ 14 C]‐octatriacontane was synthesized from 1 mCi [1‐ 14 C]stearic acid in a radiochemical yield of 20%. The key features of this synthesis were two consecutive alkylations of tosylmethyl isocyanide followed by acid hydrolysis to [18‐ 14 C]‐19‐octatriacontanone and modified Wolff‐Kishner reduction to the n‐alkane. After purification on silica gel 25 mg of [18‐ 14 C]octatriacontane was obtained with a total radioactivity of 200 μCi, a specific activity of 4.3 mCi/mmol, and a radiochemical purity in excess of 98% by thin layer radiochromatography. The method has also been applied to the synthesis of unlabeled n‐pentatriacontane and is considered to be generally applicable to the synthesis of radiolabeled alkanes from radiolabeled fatty acids.