p-Coumaric acid ethyl ester Chemical Properties

storage temp. 

2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

color 

Light yellow to light brown

Safety Information

HS Code 

2918290090

p-Coumaric acid ethyl ester Usage And Synthesis

Uses

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].

Definition

ChEBI: Ethyl p-coumarate is a cinnamate ester.

Synthesis

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).

target

Carbonic Anhydrase

References

[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

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