A question for chemists:
Does acidity affect the stability of epoxy fatty acids during liquid-liquid extraction?
In other words, if formic acid was added to Ethyl Acetate before the liquid-liquid extraction of plasma, is there any possibility of a nucleophilic attack on the protonated epoxy group at pH 2.4?
Is there any possible way to figure out what is the suitable pH to avoid such scenario?
Note: The pKa of the majority of expoxy fatty acids under investigation is around 4.4. That is why, acidifying the sample before extraction should increase the extraction yield.
Dear Sir. Concerning your issue about the stability of epoxy fatty acids under acidic conditions . Since the epoxy fatty acids seemed to be a potential lipid oxidation marker, it is important to understand its formation and stability in the food. Food being a complex matrix, it is better to start with a simple model system to study its formation during lipid oxidation. At first, it is necessary to confirm its stability before the study on the formation in the model system can be carried out. Therefore, this experiment was carried out in the casein stabilized o/w emulsions using saturated oil spiked with methyl-cis-9,10-ES. Initially, the experiment was performed using the emulsion prepared with two buffer systems, phosphate buffer at pH 7.4. and 12.0 and citrate buffer at pH 5.0 and 7.0. The two buffer systems were chosen so as to cover the wide pH range from 5.0 to 12.0. The spiked epoxy compound was monitored during storage in the dark at 25 oC. I think the following below links may help you in your analysis:
https://lib.ugent.be/fulltxt/RUG01/002/305/149/RUG01-002305149_2016_0001_AC.pdf
https://www.openagrar.de/servlets/MCRFileNodeServlet/Document_derivate_00011677/EuJLipSci_116_707-715_Bruehl_manu.pdf
Thanks
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