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Details

Stereochemistry ACHIRAL
Molecular Formula C12H14O4
Molecular Weight 222.2372
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ETHYL FERULATE

SMILES

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

InChI

InChIKey=ATJVZXXHKSYELS-FNORWQNLSA-N
InChI=1S/C12H14O4/c1-3-16-12(14)7-5-9-4-6-10(13)11(8-9)15-2/h4-8,13H,3H2,1-2H3/b7-5+

HIDE SMILES / InChI

Molecular Formula C12H14O4
Molecular Weight 222.2372
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/22324721 | https://www.ncbi.nlm.nih.gov/pubmed/24941338 | https://www.ncbi.nlm.nih.gov/pubmed/27711798 | https://www.ncbi.nlm.nih.gov/pubmed/15826020 | https://goo.gl/QGmZUK

Ethyl Ferulate is an ester type of Ferulic Acid and has powerful antioxidant, free radical scavenging and UV adsorption properties. Ethyl Ferulate can be incorporated into various cosmetic formulations including aqueous, ethanolic and emulsion-based creams, sun creams or moisturizers. Ethyl ferulate demonstrated the cytoprotective effects against oxidative damage in neuronal cells. Ethyl ferulate has also been widely studied and some recent findings include its anticholinesterase activity; inhibition of nuclear factor-kappa B (NF-κB) activity in LPS-stimulated RAW 264.7 macrophages; inhibition of inducible nitric oxide synthase (iNOS) induction in UV-induced oxidative stress in melanocytes; induction of heme oxygenase (HO-1) activity in rat astrocytes and neurons, which is a putative pathway against oxidative stress that underline neurodegenerative diseases; and cytoprotective effect against reactive oxygen species (ROS)-induced damage through the stimulation of dermal fibroblasts stress response.

Originator

Sources: Science Reports of the Tohoku Imperial University, Series 1: Mathematics, Physics, Chemistry (1929), 18, (1st Ser.), 619-23.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.7 µM [IC50]
385.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

Rats were treated with 50 and 100 mg/kg, po as a single dose.
Route of Administration: Topical
Rat type 1 astrocytes and rat hippocampal neurons were used for activity evaluation. Cells were grown in 75-cm2 flasks and maintained at 37C in a humidified atmosphere of air and 5% CO2. Confluent cells were exposed to various concentrations of EFE (Ethyl Ferulate) and RSV (trans-3,2,5-trihydrostilbene). After each treatment (6 or 24 h), cells were harvested for the determination of HO activity, HO-1 and HO-2 mRNA levels, and protein expression. Neurons growing in 24 wells were also exposed to different concentrations of EFE, and cell viability was determined at 24 h. Other neurons were pretreated for 12 h with 5 µM EFE or 5 µM EFE plus 10 µM ZnPP IX and then exposed for 2 h to 50 mU/mL GOX, before cell viability was determined.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:08:41 UTC 2023
Edited
by admin
on Fri Dec 15 16:08:41 UTC 2023
Record UNII
5B8915UELW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHYL FERULATE
INCI  
INCI  
Official Name English
ETHYL 4'-HYDROXY-3'-METHOXYCINNAMAT
Common Name English
ETHYL FERULATE [INCI]
Common Name English
NSC-14879
Code English
ORISTRACT EF
Brand Name English
NOMCORT EF
Brand Name English
2-PROPENOIC ACID, 3-(4-HYDROXY-3-METHOXYPHENYL)-, ETHYL ESTER
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C275
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
223-745-5
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY
NCI_THESAURUS
C83699
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY
RXCUI
1420983
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY RxNorm
NSC
14879
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY
MESH
C099085
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY
DRUG BANK
DB11285
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY
DAILYMED
5B8915UELW
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY
FDA UNII
5B8915UELW
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID001021502
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY
PUBCHEM
736681
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY
CAS
4046-02-0
Created by admin on Fri Dec 15 16:08:41 UTC 2023 , Edited by admin on Fri Dec 15 16:08:41 UTC 2023
PRIMARY