Facile synthesis of deuterated and [14C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools
Article first published online: 23 JUL 2013
Copyright © 2013 John Wiley & Sons, Ltd.
Journal of Labelled Compounds and Radiopharmaceuticals
Volume 56, Issue 14, pages 696–699, December 2013
How to Cite
Gordon, O. N., Graham, L. A. and Schneider, C. (2013), Facile synthesis of deuterated and [14C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools. J Label Compd Radiopharm, 56: 696–699. doi: 10.1002/jlcr.3102
- Issue published online: 16 DEC 2013
- Article first published online: 23 JUL 2013
- Manuscript Accepted: 28 JUN 2013
- Manuscript Revised: 5 JUN 2013
- Manuscript Received: 26 APR 2013
- oxidative metabolism;
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. Copyright © 2013 John Wiley & Sons, Ltd.