methyl ferulate
cinnamic acid, 4-hydroxy-3-methoxy-, methyl ester
Identification
| Name | methyl ferulate |
| IUPAC | methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate |
| CAS Number | 2309-07-1 |
| FDA UNII | Y98BUA66RX |
| Molecular Formula | C11 H12 O4 |
| Molecular Weight | 208.21344000 |
| MDL Number | MFCD00017208 |
| Nikkaji Number | J101.772A |
| Beilstein | 2731141 |
| XlogP3 | 1.80 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 338.00 to 339.00 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 0.000051 mmHg @ 25.00 °C. (est) |
| Flash Point | 267.00 °F. TCC ( 130.40 °C. ) (est) |
| logP (o/w) | 2.209 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 1189 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for methyl ferulate usage levels up to | not for fragrance use. |
| Recommendation for methyl ferulate flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
cinnamic acid, 4-hydroxy-3-methoxy-, methyl ester
ferulic acid methyl ester
ferulic acid methylester
(E)-3-(4-
hydroxy-3-methoxy-phenyl)-acrylic acid methyl ester
4-
hydroxy-3-methoxycinnamic acid methyl ester
4-
hydroxy-3-methoxycinnamic acid methylester
3-(4-
hydroxy-3-methoxyphenyl)-2-propenoic acid methyl ester
methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)acrylate
methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
methyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
(E)-
methyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
methyl 4-hydroxy-3-methoxycinnamate
methyl coniferate
2-
propenoic acid, 3- (4-hydroxy-3-methoxyphenyl)-, methyl ester
2-
propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester
2-
propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester (9CI)
2-
propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester, (2E)-
PubMed:
Overexpression of Aspergillus tubingensis faeA in protease-deficient Aspergillus niger enables ferulic acid production from plant material.
PubMed:
A halotolerant type A feruloyl esterase from Pleurotus eryngii.
PubMed:
A feruloyl esterase (FAE) characterized by relatively high thermostability from the edible mushroom Russula virescens.
PubMed:
Cloning, expression of a feruloyl esterase from Aspergillus usamii E001 and its applicability in generating ferulic acid from wheat bran.
PubMed:
Expression, purification and characterization of a feruloyl esterase A from Aspergillus flavus.
PubMed:
Three new phenanthrenes, a new stilbenoid isolated from the roots of Stemona tuberosa Lour. and their cytotoxicity.
PubMed:
Characterization of a feruloyl esterase from Lactobacillus plantarum.
PubMed:
The role of activity coefficients in bioreaction equilibria: thermodynamics of methyl ferulate hydrolysis.
PubMed:
Design, synthesis and antithrombotic evaluation of novel dabigatran prodrugs containing methyl ferulate.
PubMed:
An esterase from the basidiomycete Pleurotus sapidus hydrolyzes feruloylated saccharides.
PubMed:
Product patterns of a feruloyl esterase from Aspergillus nidulans on large feruloyl-arabino-xylo-oligosaccharides from wheat bran.
PubMed:
Enzymatic characteristics of crude feruloyl and acetyl esterases of rumen fungus Neocallimastix sp. YAK11 isolated from yak (Bos grunniens).
PubMed:
A protease-insensitive feruloyl esterase from China Holstein cow rumen metagenomic library: expression, characterization, and utilization in ferulic acid release from wheat straw.
PubMed:
A feruloyl esterase derived from a leachate metagenome library.
PubMed:
A new ferulic acid ester and other constituents from Tamarix nilotica leaves.
PubMed:
Modifying the acylation of flavonols in Petunia hybrida.
PubMed:
Influence of plant secondary metabolites on in vitro oxidation of methyl ferulate with cell wall peroxidases from lupine apoplast.
PubMed:
Phenols and lignans from Chenopodium album.
PubMed:
Antioxidant mechanism studies on ferulic acid: identification of oxidative coupling products from methyl ferulate and linoleate.
PubMed:
Antioxidant constituents from the stem of Sorghum bicolor.
PubMed:
Identification of the germination self-inhibitor from wheat stem rust uredospores.
PubMed:
Presence in Lactobacillus plantarum of an esterase active on a broad-range of phenolic esters.
PubMed:
A Chlorogenic Acid Esterase with a Unique Substrate Specificity from Ustilago maydis.
PubMed:
Stimulation of phosphorylation of ERK and CREB by phellopterin and auraptene isolated from Citrusjunos.
PubMed:
Protective effects of ferulic acid and related polyphenols against glyoxal- or methylglyoxal-induced cytotoxicity and oxidative stress in isolated rat hepatocytes.
PubMed:
Anti-inflammatory activity of methyl ferulate isolated from Stemona tuberosa Lour.
PubMed:
Feruloyl esterase from the edible mushroom Panus giganteus: a potential dietary supplement.
PubMed:
[Gene cloning, expression of a feruloyl esterase A and purification of its hydrolysis products].
PubMed:
Expression, purification and characterization of a feruloyl esterase A from Aspergillus flavus.
PubMed:
Characterization of a feruloyl esterase from Lactobacillus plantarum.
PubMed:
Product patterns of a feruloyl esterase from Aspergillus nidulans on large feruloyl-arabino-xylo-oligosaccharides from wheat bran.
PubMed:
Chemical interaction between polyphenols and a cysteinyl thiol under radical oxidation conditions.
PubMed:
A feruloyl esterase derived from a leachate metagenome library.
PubMed:
Isolation and characterization of a ferulic acid esterase (Fae1A) from the rumen fungus Anaeromyces mucronatus.
PubMed:
[Purification and characterization of ferulic acid esterase from Penicillium citrinum].
PubMed:
Thermostable feruloyl esterase for the bioproduction of ferulic acid from triticale bran.
PubMed:
Production and biochemical characterization of a type B ferulic acid esterase from Streptomyces ambofaciens.
PubMed:
A new ferulic acid ester and other constituents from Tamarix nilotica leaves.
PubMed:
Biochemical analysis of a beta-D-xylosidase and a bifunctional xylanase-ferulic acid esterase from a xylanolytic gene cluster in Prevotella ruminicola 23.
PubMed:
Modifying the acylation of flavonols in Petunia hybrida.
PubMed:
Heterocyclic compounds from Chrysanthemum coronarium L. and their inhibitory activity on hACAT-1, hACAT-2, and LDL-oxidation.
PubMed:
Influence of plant secondary metabolites on in vitro oxidation of methyl ferulate with cell wall peroxidases from lupine apoplast.
PubMed:
Rhusemialins A-C, new cyclolignan esters from the roots of Rhus javanica var. roxburghiana.
PubMed:
Antioxidant mechanism studies on ferulic acid: identification of oxidative coupling products from methyl ferulate and linoleate.
PubMed:
Structural elucidation of natural 2-hydroxy di- and tricarboxylic acids and esters, phenylpropanoid esters and a flavonoid from Autonoë madeirensis using gas chromatographic/electron ionization, electrospray ionization and tandem mass spectrometric techniques.
PubMed:
Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium caco-2 cells.
PubMed:
Purification and characterization of a type B feruloyl esterase (StFAE-A) from the thermophilic fungus Sporotrichum thermophile.
PubMed:
Antioxidant constituents from the stem of Sorghum bicolor.
PubMed:
Purification and characterization of a feruloyl esterase from Fusarium oxysporum catalyzing esterification of phenolic acids in ternary water-organic solvent mixtures.
PubMed:
A C-glucosylflavone from leaves of Piper lhotzkyanum.
PubMed:
Purification and characterization of an extracellular feruloyl esterase from the thermophilic anaerobe Clostridium stercorarium.
PubMed:
Purification and characterization of a feruloyl esterase from the fungus Penicillium expansum.
PubMed:
The faeA genes from Aspergillus niger and Aspergillus tubingensis encode ferulic acid esterases involved in degradation of complex cell wall polysaccharides.
PubMed:
Production of feruloyl/rho-coumaroyl esterase activity by Penicillium expansum, Penicillium brevicompactum and Aspergillus niger.
PubMed:
[Substituted methoxyphenol with antioxidative activity: correlation between physicochemical and biological results].
PubMed:
Degradation of feruloylated oligosaccharides from sugar-beet pulp and wheat bran by ferulic acid esterases from Aspergillus niger.
PubMed:
Aristolochic acids, aristolactam alkaloids and amides from Aristolochia kankauensis.
PubMed:
Ferulic acid esterase from Aspergillus niger: purification and partial characterization of two forms from a commercial source of pectinase.
PubMed:
Multichannel coulometric detection coupled with liquid chromatography for determination of phenolic esters in honey.
PubMed:
The purification and characterization of 4-hydroxy-3-methoxycinnamic (ferulic) acid esterase from Streptomyces olivochromogenes.
PubMed:
Methyl cinnamate derivatives enhance UV-induced mutagenesis due to the inhibition of DNA excision repair in Escherichia coli B/r.