Synthesis of Deuterated Volatile Lipid Degradation Products To Be Used as Internal Standards in Isotope Dilution Assays. 1. Aldehydes

The isotopically labeled compounds [5,6- 2 H 2 ]hexanal ( d-I ), [2,3- 2 H 2 ]-( E )-2-nonenal ( d-II ), [3,4- 2 H 2 ]-( E, E )-2,4-nonadienal ( d-III ), and [3,4- 2 H 2 ]-( E, E )-2,4-decadienal ( d-IV ) were prepared in good yields using new or improved synthesis procedures. Labeling position, chemical purity, and isotopic distribution of the compounds were characterized by various MS and NMR techniques. These molecules are used as internal standards in quantification experiments based on isotope dilution assay. Synthesis of d- I, d-III, and d-IV has not yet been reported in the literature.