Ethyl p-methoxycinnamate

• CAT Number: R061048
• CAS Number: 24393-56-4
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• Purity: ≥95%
• Synonyms: EPMC;Ethyl 4-methoxycinnamate;Ethyl para-methoxycinnamate;p-Methoxy ethyl cinnamate;para-Methoxy ethyl cinnamate
• Target: COX
• Storage: -20°C
• IUPAC Name: ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
• InChI: InChI=1S/C12H14O3/c1-3-15-12(13)9-6-10-4-7-11(14-2)8-5-10/h4-9H,3H2,1-2H3/b9-6+
• InChIKey: DHNGCHLFKUPGPX-RMKNXTFCSA-N
• SMILES: CCOC(=O)C=CC1=CC=C(C=C1)OC

Ethyl p-methoxycinnamate (EPMC) is a natural product found in K. galanga and C. zedoaria extracts with anti-inflammatory, antiangiogenic, antifungal, larvicidal, and analgesic activities. It inhibits COX-1 and COX-2 in vitro (IC50s = 1.12 and 0.83 μM, respectively) and reduces IL-1 and TNF-α production in vivo. EPMC inhibits granuloma tissue formation and acts as an analgesic, delaying tail flick time, in a dose-dependent manner in rats. It inhibits blood vessel growth in rat aortic explants (IC50 = 91.9 μg/ml). EPMC (<10 μg/ml) also reduces growth of T. rubrum, A. niger, S. cerevisiae, and E. floccosum and is larvicidal (LC50 = 53.64 ppm) against Ae. aegypti.

Reference

1.Gupta, S.K.,Banerjee, A.B., and Achari, B. Isolation of ethyl p-methoxycinnamate, the major antifungal principle of Curcumba zedoaria.. Lloydia 39(4), 218-222 (1976).