4-hydroxy Nonenal Mercapturic Acid-d₃

4-hydroxy Nonenal mercapturic acid-d₃ contains three deuterium atoms at the terminal methyl position. It is intended for use as an internal standard for the quantification of 4-HNE mercapturic acid by GC- or LC-mass spectrometry. Peroxidation of common ω-6 polyunsaturated fatty acids (PUFAs) such as linoleic acid, DGLA, and arachidonic acid can give rise to 4-HNE. 4-HNE is cleared rapidly from the plasma and undergoes enterohepatic circulation as a glutathione conjugate in the rat.¹ About two thirds of an administered dose of 4-HNE is excreted within 48 hours in the urine, primarily in the form of mercapturic acid conjugates.² The C-1 aldehyde of 4-HNE is reduced to an alcohol in about half of these metabolites. The remainder are C-1 aldehydes or have been oxidized to C-1 carboxylic acids. These aldehydes and carboxylic acids can also form γ-lactols and γ-lactones, respectively, producing at least four or five end urinary metabolites of 4-HNE in vivo.

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1. Laurent, A., Alary, J., Debrauwer, L., et al. Analysis in the rat of 4-hydroxynonenal metabolites excreted in bile: Evidence of enterohepatic circulation of these byproducts of lipid peroxidation. Chem. Res. Toxicol. 12(10), 887-894 (1999).

2. Alary, J., Bravais, F., Cravedi, J.P., et al. Mercapturic acid conjugates as urinary end metabolites of the lipid peroxidation product 4-hydroxy-2-nonenal in the rat. Chem. Res. Toxicol. 8, 34-39 (1995).