Ethyl Ferulate
Basic information
- CAS
4046-02-0- Standard SMILES
CCOC(=O)/C=C/c1ccc(O)c(OC)c1- InChIKey
ATJVZXXHKSYELS-FNORWQNLSA-N- Molecular formula
- C12H14O4
- Average molar mass
- 222.24 g/mol
Overview
ethyl ferulate has been reported in Coptis japonica, Solanum nigrum, and other organisms with data available.
Names & identifiers
- Preferred name
- Ethyl Ferulate
- IUPAC
- ethyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
- English name
- Ethyl 4-hydroxy-3-methoxycinnamate
- Molecular formula
- C12H14O4
- Molecular weight
- 222.24
Names & synonyms
Ethyl ferulate4046-02-0Ethyl 4-hydroxy-3-methoxycinnamateethyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoateFerulic acid, ethyl ester5B8915UELWORISTRACT EFNOMCORT EFNSC-14879DTXSID001021502RefChem:138929DTXCID801506566
Show more names
methoxycinnamateNSC 14879Natural Ethyl Ferulate4-HYDROXY-3-METHOXYCINNAMIC ACID ETHYL ESTERFeruLBBR 3222
ETHYL 4'-HYDROXY-3'-METHOXYCINNAMAT2-Propenoic Acid, 3-(4-Hydroxy-3-Methoxyphenyl)-, Ethyl223-745-5Ferulic acid ethyl esterEthyl 4'-hydroxy-3'-methoxycinnamate28028-62-8ethyl 3-(4-hydroxy-3-methoxyphenyl)acrylateEthyl (E)-ferulate
Database identifiers
- CAS
4046-02-0- PubChem CID
- 736681
- ChEMBL
CHEMBL286796- UNII
- 5B8915UELW
- EC Number
- 223-745-5
- Nikkaji
- J217.860E、J729.906K
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 249
Physicochemical properties
- Melting point
- 63 · 63-65 °C(lit.)
- Boiling point
- 164 · 164-166 °C0.5 mm Hg(lit.)
- Density
- 1.0643 · 1.0643 (rough estimate)
- refractive index
- 1.456 · 1.4560 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- pka
- 8.88 · 8.88±0.18(Predicted)
- form
- Solid
- color
- White to Off-White
- Sensitive
- Light Sensitive
- BRN
- 2696807 · 2696807
- Stability
- Hygroscopic, Light Sensitive
- Cosmetics Ingredients Functions
- ANTIOXIDANT
- 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+
- InChIKey
- ATJVZXXHKSYELS-FNORWQNLSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29189900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-37/39-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionFerulic acid is a hydroxycinnamic acid that is abundant in plants and originally derived from giant fennel (F. communis). This naturally-occurring phenolic has antioxidant activities that provide protection against inflammation and cancer. Ferulic acid ethyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes. Ferulic acid ethyl ester has less antioxidant capacity than ferulic acid in neuronal PC12 cells (IC50 = 66.7 μM for ferulic acid ethyl ester vs. 44.6 μM for ferulic acid, 2,2-diphenyl-1-picrylhydrazyl radical scavenging). However, ferulic acid ethyl ester increases the expression of heme oxygenase-1, Hsp70, and Hsp72, providing neuroprotection against amyloid β-peptide. Moreover, ferulic acid ethyl ester (25 μM) completely prevents cytotoxicity induced by ultraviolet B irradiation of normal human epidermal melanocytes, again associated with an induced expression of heme oxygenase-1 and Hsp70.
UsesFerulic acid ethyl ester is an ethyl ester derivative of Ferulic acid (F308900), which is used as an antioxidant and food preservative.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
15 records
Compound notes
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