Synthesis of [¹⁴CO]ellagic acid

Abstract

lCQ]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 14CO2 with lithiated 3.43-trimethoxybenzene and demethylation of the resulting 3.4,5-trimethoxyben~c acid was followed by esterifcation 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, tyrosinme. The latter method produced the highest yield and purity. This preparation produced [1a]ellagic acid with a specific activity of 20 mCi/mmol. The yields of labeled 3,4,5-trimethoxybenzoic acid and ellagic acid based on Bal4COj were 65% and 16%. respectively.

Site-specific accumulation of the cancer preventive dietary polyphenol ellagic acid in epithelial cells of the aerodigestive tract

“…[ 14 C]Ellagic acid ( Figure 1) was synthesized with a specific activity of 20 mCi mmol −1 at the Ohio State University Comprehensive Cancer Center (Zeng et al 1991) and was a kind gift from Dr Gary Stoner, Ohio State. TS-2 tissue solubilizer was obtained from Research Products International (Mt Prospect, IL).…”

THE DIETARY POLYPHENOL ELLAGIC ACID IS A POTENT INHIBITOR OF hOAT1

“…14 C]Ellagic acid was synthesized with a specific activity of 20 mCi/mmol at the Ohio State University Comprehensive Cancer Center (Zeng et al, 1991) Xenopus laevis Oocyte Uptake Assay. X. laevis oocytes were obtained as described previously (Youngblood and Sweet, 2004).…”

First synthesis of [1,3,5-13C3]gallic acid

“…HPLC retention times can also be affected by the presence of deuterium. 5,6 Two routes to [carboxy- 14 C]gallic acid have been reported, by Zeng et al 7 and Schildknecht et al, 8 employing 14 CO 2 as the labelled species, but no syntheses of any ring-labelled versions have been reported.…”

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An efficient and high-yielding synthesis for [1,3,[5][6][7][8][9][10][11][12][13] C 3 ]gallic acid from non-aromatic precursors is presented. [3,[5][6][7][8][9][10][11][12][13] C 2 ]4H-Pyran-4-one was first prepared from the reaction between triethyl orthoformate and [1,3-13 C 2 ]acetone. The third 13 C-atom was introduced into the ring by reaction of the pyranone with diethyl [2-13 C]malonate.

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“…Subsequent hydrolysis of the ester and substitution of the bromine atoms with hydroxyl groups was achieved under basic conditions in a single step to yield the desired [1,3,5-13 C 3 ]gallic acid. The synthesis of [2,[6][7][8][9][10][11][12][13] C 2 ]4H-pyran-4-one is also presented to demonstrate the potential of the methodology for the regioselective placement of 13 C-atoms into benzene rings.…”