15212-09-6Relevant articles and documents
Labelled compounds of interest as antitumour agents - VII(I) [2H]- and [14C]-Curcumin
Parveen, Ifat,Threadgill, Michael D.
, p. 883 - 889 (2000)
Curcumin (E,E-1,7-di(4-hydroxy-3-methoxyphenyl)-3-hydroxyhepta-1,3,6-trien-5-one) is an investigational cancer chemopreventive agent. Lithium-bromine exchange of 1-bromo-4-(1-ethoxyethyl)-3-methoxybenzene with butyl lithium, quench with O2HCNMe2 and acidic work-up gave 4-hydroxy-3-methoxybenz-[2H]-aldehyde ([2H]-vanillin) in 27% yield (based on O2HCNMe2). Condensation with pentane-2,4-dione then gave E,E-1,7-di(4-hydroxy-3-methoxyphenyl)-3-hydroxy-1,7-di-[2H]-hepta-1,3,6-trien-5-one ([2H2]-curcumin). Adaptation of the procedures and use of OH14CNMe2 provided [14C]-curcumin (specific radioactivity 12.7 MBq mmol-1) via [14C]-vanillin.