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Synthesis of [ 14 CO]ellagic acid
Author(s) -
Zeng Wenguang,
Heur YoungHun,
Kinstle Thomas H.,
Stoner Gary D.
Publication year - 1991
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.2580290607
Subject(s) - ellagic acid , chemistry , demethylation , yield (engineering) , nuclear chemistry , propyl gallate , organic chemistry , methyl gallate , chromatography , polyphenol , gallic acid , antioxidant , biochemistry , gene expression , materials science , metallurgy , dna methylation , gene
[ 14 CO]Ellagic acid with a chemical purity of 98.9% and radiochemical purity of 99.9% was synthesized with an overall yield of 16% (both chemically and radiochemically). Reaction of 14 CO 2 with lithiated 3,4,5‐trimethoxybenzene and demethylation of the resulting 3,4,5‐trimethoxybenzoic acid was followed by esterification and coupling of methyl gallate into ellagic acid. Two efficient coupling methods were employed: direct aeration and aeration of methyl gallate in the presence of the phenolic oxidase, tyrosinase. The latter method produced the highest yield and purity. This preparation produced [ 14 CO]ellagic acid with a specific activity of 20 mCi/mmol. The yields of labeled 3,4,5‐trimethoxybenzoic acid and ellagic acid based on Ba 14 CO 3 were 65% and 16%, respectively.