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ChEBI: 4-hydroxycinnamaldehyde is a cinnamaldehyde that is (E)-cinnamaldehyde substituted at position 4 on the phenyl ring by a hydroxy group. It has a role as an apoptosis inducer, an EC 1.14.13.39 (nitric oxide synthase) inhibitor and a plant metabolite. It is functionally related to an (E)-cinnamaldehyde.

General procedure for the synthesis of 3-(4-hydroxyphenyl)acrolein from the compound (CAS:103909-81-5): general method: compounds 8a2, 8b2 and 8d2 were dissolved in methanol and catalytic amount of p-toluenesulfonic acid (p-TsOH) was added. After stirring the reaction mixture for 1 h at room temperature, the solvent was removed by distillation under reduced pressure. Water was added to the residue and extracted with ethyl acetate (EtOAc). The organic layers were combined and dried with anhydrous sodium sulfate (Na2SO4) followed by evaporation of the solvent under vacuum. The residue was purified by column chromatography to afford the target product 3-(4-hydroxyphenyl)acrolein and its analogs 8a1, 8b1 and 8d1.

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