We trying to protect the hydroxy groups of Ellagic acid with either methyl iodide (to concert them to methods groups) or acetyl group with acetic anhydride or any other group. However, poor solubility of Ellagic acid was the obstacle in any reaction for it. If anyone dealt with ellagic acid can give any suggestion, will be appreciated.
Dear Sinan,
sorry to see that your very interesting technical question has not yet received any expert answers. It is often not a real obstacle when starting materials have a poor solubility. Reactions like methylation or acetylation can the be carried out in suspension and the more soluble reaction product will slowly form, while at the same time the poorly soluble precursor dissolves. You will certainly be pleased to see that the tetra-acetylated ellagic acid (= ellagic acid peracetate) has already been reported in the previous literature. It is described in the following article:
Ellagic acid peracetate is superior to ellagic acid in the prevention of genotoxicity due to aflatoxin B1 in bone marrow and lung cells
https://academic.oup.com/jpp/article/59/1/81/6147932
This useful article is freely available as public full text on the internet (please see attached pdf file). In the same manner you could try to make tetramethyl ellagic acid (I did not check if this compound has been described before) by treatment of ellagic acid with an excess of methyl iodide in pyridine.
Good luck with your experiments and best wishes, Frank Edelmann
P.S. I just found out that tetramethyl ellagic acid has also been reported in the literature. For a synthetic procedure, please have a look at the following RG link:
The Further Chemistry of Ellagic Acid: I. Synthesis of Tetramethylellagic Acid and Associated Polymer PrecursorsArticle The Further Chemistry of Ellagic Acid: I. Synthesis of Tetra...
The paper is freely available as public full text on RG. The authors used dimethyl sulfate as methylation reagent. Just in case that you plan to repeat this reaction: Be very careful when working with dimethyl sulfate as this compound is highly toxic! Always handle dimethyl sulfate in a well-ventilated fume hood and wear protective gloves.
Hi Dr Sinan Battah . I found in the internet that Ellagic acid is soluble in DMSO, which should be purged with an inert gas. The solubility of ellagic acid in DMSO is approximately 0.14 mg/ml. Ellagic acid is sparingly soluble in aqueous buffers. An aqueous solution can best be prepared by diluting the organic solution into aqueous buffers or isotonic saline. See the link: https://www.caymanchem.com/pdfs/10569.pdf
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