3-(4-hydroxyphenyl)acrylaldehyde

Uses

p-Coumaraldehyde is a potential antitumor agents extracted from cucumbers. p-Coumaraldehyde was shown to significantly inhibit the cancer cell growth in a dose-dependent manner

Definition

ChEBI: A cinnamaldehyde that is (E)-cinnamaldehyde substituted at position 4 on the phenyl ring by a hydroxy group.

Synthesis

General method: compounds 8a2, 8b2 and 8d2 were dissolved in methanol and a catalytic amount of p-toluenesulfonic acid (p-TsOH) was added. After stirring the reaction mixture for 1 h at room temperature, the solvent was evaporated under reduced pressure. Water was added to the residue and extracted with ethyl acetate (EtOAc). The organic layers were combined and dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford analogs 8a1, 8b1 and 8d1 of the target product 3-(4-hydroxyphenyl)acrolein.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 13, p. 2839 - 2844