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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

Molecular Formula C12H14O3
Molecular Weight 206.2378
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6652816 | https://www.ncbi.nlm.nih.gov/pubmed/22825623 | https://www.ncbi.nlm.nih.gov/pubmed/21459133 | https://www.ncbi.nlm.nih.gov/pubmed/21459133 | https://www.ncbi.nlm.nih.gov/pubmed/27720847 | https://www.ncbi.nlm.nih.gov/pubmed/785141

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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Ethyl p-methoxycinnamate isolated from a traditional anti-tuberculosis medicinal herb inhibits drug resistant strains of Mycobacterium tuberculosis in vitro.
2011 Jul
Patents

Sample Use Guides

Rat: 100 mg/kg, 200 mg/kg, 400 mg/kg and 800 mg/kg
Route of Administration: Oral
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:50:09 GMT 2023
Edited
by admin
on Sat Dec 16 01:50:09 GMT 2023
Record UNII
SD418S06XD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHYL METHOXYCINNAMATE
INCI  
INCI  
Official Name English
METHYL-P-COUMARIC ACID, ETHYL ESTER
Common Name English
ETHYL (E)-3-(4-METHOXYPHENYL)-2-PROPENOATE
Systematic Name English
ETHYL (E)-P-METHOXYCINNAMATE
Common Name English
ETHYL TRANS-P-METHOXYCINNAMATE
Common Name English
ETHYL METHOXYCINNAMATE [INCI]
Common Name English
(2E)-3-(4-METHOXYPHENYL)-2-PROPENOIC ACID ETHYL ESTER
Systematic Name English
3-(4-METHOXYPHENYL)-2-PROPENOIC ACID, ETHYL ESTER
Common Name English
3-(METHOXYPHENYL)-2-PROPENOIC ACID, ETHYL ESTER
Common Name English
SOLABOOST SPF
Brand Name English
ETHYL (E)-4-METHOXYCINNAMATE
Systematic Name English
UVSOB B
Brand Name English
ETHYL (E)-3-(P-METHOXYPHENYL)-2-PROPENOATE
Common Name English
ETHYL 3-(4-METHOXYPHENYL)-2-PROPENOATE
Systematic Name English
2-PROPENOIC ACID, 3-(4-METHOXYPHENYL)-, ETHYL ESTER, (E)-
Common Name English
Code System Code Type Description
EVMPD
SUB35649
Created by admin on Sat Dec 16 01:50:09 GMT 2023 , Edited by admin on Sat Dec 16 01:50:09 GMT 2023
PRIMARY
PUBCHEM
5281783
Created by admin on Sat Dec 16 01:50:09 GMT 2023 , Edited by admin on Sat Dec 16 01:50:09 GMT 2023
PRIMARY
FDA UNII
SD418S06XD
Created by admin on Sat Dec 16 01:50:09 GMT 2023 , Edited by admin on Sat Dec 16 01:50:09 GMT 2023
PRIMARY
CAS
24393-56-4
Created by admin on Sat Dec 16 01:50:09 GMT 2023 , Edited by admin on Sat Dec 16 01:50:09 GMT 2023
PRIMARY
RXCUI
2468050
Created by admin on Sat Dec 16 01:50:09 GMT 2023 , Edited by admin on Sat Dec 16 01:50:09 GMT 2023
PRIMARY
SMS_ID
100000128536
Created by admin on Sat Dec 16 01:50:09 GMT 2023 , Edited by admin on Sat Dec 16 01:50:09 GMT 2023
PRIMARY