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Details

Stereochemistry ACHIRAL
Molecular Formula C12H14O3
Molecular Weight 206.2378
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ETHYL METHOXYCINNAMATE

SMILES

CCOC(=O)\C=C\C1=CC=C(OC)C=C1

InChI

InChIKey=DHNGCHLFKUPGPX-RMKNXTFCSA-N
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+

HIDE SMILES / InChI

Description

Ethyl Methoxycinnamate (EPMC , Ethyl-p-methoxycinnamate) is a major constituent of Kaempferia galanga. with nematicidal, mosquito repellent, anti-neoplastic and anti-microbial activity. In preclinical studies Ethyl Methoxycinnamate shows marked larvicidal, antifungal and anti-inflammatory activities as well as inhibitory activity on susceptible and multi-drug resistant (MDR) clinical M. tuberculosis strains isolated from tuberculosis patients as well. In an in vitro anti-inflammatory mechanistic study, Ethyl Methoxycinnamate was found to inhibit both COX-1 and COX-2.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.12 µM [IC50]
0.83 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rat: 100 mg/kg, 200 mg/kg, 400 mg/kg and 800 mg/kg
Route of Administration: Oral
In Vitro Use Guide
Cytotoxicity of EPMC on human monocytic leukemic cell lines THP-1 was analysed by 3-(4,5-dimethylthiazol-2-yl)- 2,5-diphenyltetrazolium (MTT) assay. THP-1 cells were seeded in 96-well microtitre plate at a density of 2×10^4 cells/well in quadruplicates. Various concentrations of EPMC (Ethyl Methoxycinnamate) in RPMI medium containing 10% foetal bovine serum (FBS) were added to the wells. Control wells did not contain EPMC. The cells were incubated at 37 °C in the presence of 5% CO2. After 24 h, 100 μl MTT (2.5 mg/ml stock) dissolved in RPMI was added and again incubated at 37 °C. After two hours, 100 μl of lysis buffer (20% SDS in 50% DMF) was added and incubated at 37 °C. The plate was read at 570 nm after 6 h and percentage viability of cells was calculated.