A cinnamic acid ester with diverse biological activities
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Ethyl p-methoxycinnamate

Item No. 11740

Technical Information
Formal Name
3-(4-methoxyphenyl)-2E-propenoic acid, ethyl ester
CAS Number
24393-56-4
Synonyms
  • EPMC
  • Ethyl 4-methoxycinnamate
  • Ethyl para-methoxycinnamate
Molecular Formula
C12H14O3
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 10 mg/ml
λmax
277, 310 nm
SMILES
O=C(OCC)/C=C/C1=CC=C(OC)C=C1
InChi Code
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+
InChi Key
DHNGCHLFKUPGPX-RMKNXTFCSA-N
Origin
Plant/Hedychium spicatum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ethyl p-methoxycinnamate (EPMC) is a cinnamic acid ester that has been found in K. galanga and has diverse biological activities.1,2,3 It is active against T. rubrum, A. niger, S. cerevisiae, and E. floccosum when used at concentrations less than 10 μg/ml.1 EPMC inhibits COX-1 and COX-2 in vitro (IC50s = 1.12 and 0.83 μM, respectively).2 It inhibits microvessel sprouting in isolated rat aortic rings (IC50 = 91.9 µg/ml).4 In vivo, EPMC (60 mg/kg) reduces IL-1 and TNF-α production and inhibits granuloma formation in a rat model of cotton pellet-induced granuloma formation. It also increases the latency to tail withdrawal in a hot plate test in rats when administered at doses ranging from 200 to 800 mg/kg.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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).

    2. Umar, M.I., Asmawi, M.Z., Sadikun, A., et alBioactivity-guided isolation of ethyl-p-methoxycinnamate, an anti-inflammatory constituent, from Kaempferia galanga L. extracts. Molecules 17(7), 8720-8734 (2012).

    3. Umar, M.I., Asmawi, M.Z., Sadikun, A., et alEthyl-p-methoxycinnamate isolated from Kaempferia galanga inhibits inflammation by suppressing interleukin-1, tumor necrosis factor-α, and angiogenesis by blocking endothelial functions. Clinics (Sao Paulo) 69(2), 134-144 (2014).

    4. Georgopoulou, K., Smirlis, D., Bisti, S., et alIn vitro activity of 10-deacetylbaccatin III against Leishmania donovani promastigotes and intracellular amastigotes. Planta Med. 73(10), 1081-1088 (2007).