CAS 2309-07-1 Methyl 4-hydroxy-3-methoxy-cinnamate (HCID 16830)

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Basic information

CAS: 2309-07-1
Standard SMILES: COC(=O)C=Cc1ccc(O)c(OC)c1
InChIKey: AUJXJFHANFIVKH-UHFFFAOYSA-N
Molecular formula: C11H12O4
Average molar mass: 208.21 g/mol
Monoisotopic mass: 208.07355886

Overview

methyl (EZ)-ferulate has been reported in Iris milesii, Hibiscus taiwanensis, and other organisms with data available.

Names & identifiers

Preferred name: Methyl 4-hydroxy-3-methoxy-cinnamate
IUPAC: methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
English name: Ferulic acid methyl ester
Molecular formula: C11H12O4
Molecular weight: 208.21

Names & synonyms

methyl 4-hydroxy-3-methoxy-cinnamateRefChem:1089473methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoateSCHEMBL510492orb1303446AUJXJFHANFIVKH-UHFFFAOYSA-Nmethyl 3-methoxy-4-hydroxycinnamates5451METHYL-4-HYDROXY-3-METHOXYCINNAMATEmethyl 3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate4-HYDROXY-3-METHOXYCINNAMIC ACID METHYL ESTERMETHYL FERULATE

Show more names

METHYL 4-HYDROXY-3-METHOXYCINNAMATEtrans-methylferulateMethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester4-hydroxy-3-methoxycinnamateMaritin Frans-methylferulate4-HYDROXY-3-METHOXYCINNAFerulic acid methyl este

Database identifiers

CAS

Properties

Computed structural properties

XLogP: 1.8
Topological polar surface area: 55.8 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 15
Formal charge: 0
Complexity: 237

Physicochemical properties

Melting point: 62 · 62-65°C
Boiling point: 163 °C · 163 °C(Press: 1 Torr)
Density: 1.204 · 1.204±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: Acetone (Slightly), Chloroform (Slightly), Ethyl Acetate (Sparingly)
form: Solid
pka: 8.88 · 8.88±0.18(Predicted)
color: White to Off-White
Water Solubility: Slightly soluble in water.
InChI: InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3
InChIKey: AUJXJFHANFIVKH-UHFFFAOYSA-N
SMILES: C(OC)(=O)C=CC1=CC=C(O)C(OC)=C1
LogP: 2.209 · 2.209 (est)
CAS DataBase Reference: 2309 · 2309-07-1(CAS DataBase Reference)
FDA UNII: 98 BUA66RX · Y98BUA66RX

Safety & regulation

Safety data

rtecs: GD9470000
hs_code: 2918999090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 26-36/37/39
Hazard statements: H315-H319-H335
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 2 items

UsesFerulic 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 methyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes. Ferulic acid methyl ester has less antioxidant capacity than ferulic acid in neuronal PC12 cells (IC50 = 74.7 μM for ferulic acid ethyl ester vs. 44.6 μM for ferulic acid, 2,2-diphenyl-1-picrylhydrazyl radical scavenging). Ferulic acid methyl ester, at 10-25 μg/ml, inhibits the release of pro-inflammatory cytokines, blocks the expression of COX-2, and reduces nitric oxide generation from LPS-stimulated macrophages.

UsesFerulic Acid Methyl Ester is a derivative of Ferulic Acid (F308900), used as an antioxidant and food preservative. It has less antioxidant capacity than ferulic acid.