7362-39-2

p-Coumaric Acid Ethyl Ester is the ethyl ester of p-Coumaric acid[1]. p-Coumaric Acid is a potential immunosuppressive agent in treating autoimmune inflammatory diseases like rheumatoid arthritis[1].

ChEBI: Ethyl p-coumarate is a cinnamate ester.

The general procedure for the synthesis of ethyl 3-(4-hydroxyphenyl)acrylate from 4-iodophenol and ethyl acrylate was carried out as follows: a mixture of 4-iodophenol (5 g, 22.93 mmol), ethyl acrylate (4.587 g, 45.87 mmol), and potassium carbonate (6.330 g, 45.87 mmol) was dissolved in DMF (15 ml), followed by addition of SS- Pd catalyst (10.27 g, 2 mol% Pd). The reaction mixture was heated and stirred at 100 °C for 6 h under nitrogen protection. After completion of the reaction, it was cooled to room temperature and the reaction mixture was diluted with ethyl acetate (15 ml) and washed with cold water. The organic layer was further washed with brine and dried over anhydrous Na2SO4. The crude product was purified by column chromatography (eluent: EtOAc/hexane, 1:99) to afford ethyl (E)-3-(4-hydroxyphenyl)acrylate as a colorless liquid (4.051 g, 93% yield).

Carbonic Anhydrase

[1] T. Silva, et al. Hydroxycinnamic acid as a novel scaffold for the development of cyclooxygenase-2 inhibitors. RSC Advances. Issue 72, 2015.
[2] Pragasam SJ,?et al. Immunomodulatory and anti-inflammatory effect of?p-coumaric acid, a common dietary polyphenol on experimental inflammation in rats. Inflammation.?2013 Feb;36(1):169-76. DOI:10.1007/s10753-012-9532-8