Facile synthesis of deuterated and 14Clabeled analogues of vanillin and curcumin for use as mechanistic and analytical tools

摘要

Curcumin is a dietary diphenol with antioxidant, antinflammatory and antitumor activity. We describe facile procedures for the synthesis of [¹⁴C2]curcumin (4 mCi/mmol), [d6]curcumin, [d3]curcumin, [¹³C5]curcumin, and [d6]bicyclopentadione, the major oxidative metabolite of curcumin. We also describe synthesis of the labeled building blocks [¹⁴C]vanillin, [d3]vanillin, and [¹³C5]acetylacetone. The overall molar yields of the labeled products were 52% ([¹⁴C]) and 47% ([d3]) for vanillin and 25% ([¹⁴C2]) and 27% ([d6]) for curcumin. The compounds can be used as radiotracers in biotransformation studies and as isotopic standards for mass spectrometry-based quantification in pharmacokinetic analyses.