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Synthesis of 13 C‐ and 14 C‐labeled ellagic acid
Author(s) -
Mishra Nrusingha C.,
Gold Barry
Publication year - 1990
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.2580280807
Subject(s) - chemistry , ellagic acid , gallic acid , high performance liquid chromatography , column chromatography , chromatography , nuclear chemistry , radiochemistry , organic chemistry , antioxidant , polyphenol
The syntheses of [ 13 C]‐ and [ 14 C]ellagic acid ( EA ) were accomplished by reacting [ 13 C]‐ or [ 14 C]CO 2 with metalated 3,4,5‐trimethoxybenzene to afford trimethylgallic acid which was O‐demethylated with hydroiodic acid. Oxidation of the resulting labeled gallic acid with potassium persulfate produced EA. The yields of trimethylgallic acid and EA based on [ 14 C]BaCO 3 are 48 and 1%, respectively. Final purification of EA involved the use of preparative reversed‐phase HPLC and removal of the eluent buffer salts on a C 18 Sep‐Pak column. The isotopic purity of [ 13 C] EA was determined by 13 C NMR. The [ 14 C] EA had 99% radiochemical purity as determined by analytical HPLC and a specific activity of ca. 110 mCi/mmol.