methyl caffeate
2-propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester, (2E)-
Identification
| Name | methyl caffeate |
| IUPAC | methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
| CAS Number | 3843-74-1 |
| FDA UNII | N79173B9HF |
| Molecular Formula | C10 H10 O4 |
| Molecular Weight | 194.18650000 |
| MDL Number | MFCD00210468 |
| Nikkaji Number | J46.681F |
| XlogP3 | 1.50 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 367.60 °C. @ 760.00 mm Hg (est) |
| Flash Point | 299.00 °F. TCC ( 148.30 °C. ) (est) |
| logP (o/w) | 1.190 (est) |
| Soluble in | water, 1.142e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| 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 caffeate usage levels up to | not for fragrance use. |
| Recommendation for methyl caffeate flavor usage levels up to | not for flavor use. |
Potential Uses
Natural Occurrence
Synonyms
caffeic acid methyl ester
caffeic acid, methyl ester
(E)-3-(3,4-
dihydroxy-phenyl)-acrylic acid methyl ester
methyl (2E)-3-(3,4-dihydroxyphenyl)acrylate
methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
methyl 3,4-dihydroxycinnamate
2-
propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester, (2E)-
PubMed:
A Chlorogenic Acid Esterase with a Unique Substrate Specificity from Ustilago maydis.
PubMed:
K20E, an oxidative-coupling compound of methyl caffeate, exhibits anti-angiogenic activities through down-regulations of VEGF and VEGF receptor-2.
PubMed:
Cytotoxic constituents of Abutilon indicum leaves against U87MG human glioblastoma cells.
PubMed:
Antioxidant, 5-lipoxygenase inhibitory and cytotoxic activities of compounds isolated from the Ferula lutea flowers.
PubMed:
Isolation, identification and antioxidant activity of bound phenolic compounds present in rice bran.
PubMed:
Isolation of benzoic and cinnamic acid derivatives from the grains of Sorghum bicolor and their inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells.
PubMed:
Application of two newly identified and characterized feruloyl esterases from Streptomyces sp. in the enzymatic production of ferulic acid from agricultural biomass.
PubMed:
Leaf extract of Markhamia platycalyx: polyphenolic profile, acute toxicity, anti-inflammatory, hepatoprotective and in vitro antioxidant activities.
PubMed:
A novel continuous flow biosynthesis of caffeic acid phenethyl ester from alkyl caffeate and phenethanol in a packed bed microreactor.
PubMed:
Antimicrobial and Antimycobacterial Activities of Methyl Caffeate Isolated from Solanum torvum Swartz. Fruit.
PubMed:
A feruloyl esterase (FAE) characterized by relatively high thermostability from the edible mushroom Russula virescens.
PubMed:
Rapid synthesis of propyl caffeate in ionic liquid using a packed bed enzyme microreactor under continuous-flow conditions.
PubMed:
Expression, purification and characterization of a feruloyl esterase A from Aspergillus flavus.
PubMed:
Characterization of a feruloyl esterase from Lactobacillus plantarum.
PubMed:
Antiproliferative Effect and the Isolated Compounds of Pouzolzia indica.
PubMed:
A novel chemoenzymatic synthesis of propyl caffeate using lipase-catalyzed transesterification in ionic liquid.
PubMed:
Metagenomic mining of feruloyl esterases from termite enteric flora.
PubMed:
Detection of a plant enzyme exhibiting chlorogenate-dependant caffeoyltransferase activity in methanolic extracts of arbuscular mycorrhizal tomato roots.
PubMed:
Chemical evidence for the synergistic effect of a cysteinyl thiol on the antioxidant activity of caffeic and dihydrocaffeic esters.
PubMed:
Natural compounds against Alzheimer's disease: molecular recognition of Aβ1-42 peptide by Salvia sclareoides extract and its major component, rosmarinic acid, as investigated by NMR.
PubMed:
Antiproliferative and apoptotic effects of the oxidative dimerization product of methyl caffeate on human breast cancer cells.
PubMed:
An esterase from the basidiomycete Pleurotus sapidus hydrolyzes feruloylated saccharides.
PubMed:
Clerodendranoic acid, a new phenolic acid from Clerodendranthus spicatus.
PubMed:
Chemical interaction between polyphenols and a cysteinyl thiol under radical oxidation conditions.
PubMed:
An unusual caffeic acid derived bicyclic [2.2.2] octane lignan and other constituents from Cordia rufescens.
PubMed:
Study on the phenolic constituents of the flowers and leaves of Trifolium repens L.
PubMed:
Chemical constituents of Stereospermum acuminatissimum and their urease and α-chymotrypsin inhibitions.
PubMed:
Expression, characterization and structural modelling of a feruloyl esterase from the thermophilic fungus Myceliophthora thermophila.
PubMed:
Antihyperglycemic activity and antidiabetic effect of methyl caffeate isolated from Solanum torvum Swartz. fruit in streptozotocin induced diabetic rats.
PubMed:
[Aromatic constituents of Heteroplexis micocephal and their bioactivities].
PubMed:
CCoAOMT suppression modifies lignin composition in Pinus radiata.
PubMed:
[Purification and characterization of ferulic acid esterase from Penicillium citrinum].
PubMed:
[Flavonoids and phenolic acid derivatives from flos farfarae].
PubMed:
Identifying new lignin bioengineering targets: 1. Monolignol-substitute impacts on lignin formation and cell wall fermentability.
PubMed:
Enzymatic synthesis of caffeic acid phenethyl ester analogues in ionic liquid.
PubMed:
Methyl caffeate as an alpha-glucosidase inhibitor from Solanum torvum fruits and the activity of related compounds.
PubMed:
[Chemical constituents of Incarvillea younghusbandii].
PubMed:
Characterization of two distinct feruloyl esterases, AoFaeB and AoFaeC, from Aspergillus oryzae.
PubMed:
A new steroidal glycoside and a new phenyl glycoside from a ripe cherry tomato.
PubMed:
Antioxidation mechanism studies of caffeic acid: identification of antioxidation products of methyl caffeate from lipid oxidation.
PubMed:
New caffeoyl derivatives from the leaves of Davidia involucrata.
PubMed:
Quantitative determination of fluorinated caffeic acid phenethyl ester derivative from rat blood plasma by liquid chromatography-electrospray ionization tandem mass spectrometry.
PubMed:
Triterpenoid saponins from the seeds of Pharbitis nil.
PubMed:
Dispersion behavior of zirconia nanocrystals and their surface functionalization with vinyl group-containing ligands.
PubMed:
Exploration of members of Aspergillus sections Nigri, Flavi, and Terrei for feruloyl esterase production.
PubMed:
Inhibition of respiratory burst in human neutrophils and lipoxygenase enzyme by compounds from Haloxylon griffithii.
PubMed:
Polyphenolic constituents of Actaea racemosa.
PubMed:
Synthesis of the saccharomicin fucose-aglycon conjugate and determination of absolute configuration.
PubMed:
Probing the determinants of substrate specificity of a feruloyl esterase, AnFaeA, from Aspergillus niger.
PubMed:
Effects of CAPE-like compounds on HIV replication in vitro and modulation of cytokines in vivo.
PubMed:
Cytotoxic constituents of roots of Chaerophyllum hirsutum.
PubMed:
Phenolic acid derivatives with potential anticancer properties--a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids.
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:
Purification and properties of a feruloyl esterase involved in lignocellulose degradation by Aureobasidium pullulans.
PubMed:
Purification and characterization of a feruloyl esterase from Fusarium oxysporum catalyzing esterification of phenolic acids in ternary water-organic solvent mixtures.
PubMed:
A non-modular type B feruloyl esterase from Neurospora crassa exhibits concentration-dependent substrate inhibition.
PubMed:
Black cohosh (Cimicifuga racemosa L.) protects against menadione-induced DNA damage through scavenging of reactive oxygen species: bioassay-directed isolation and characterization of active principles.
PubMed:
Cimiracemates A-D, phenylpropanoid esters from the rhizomes of Cimicifuga racemosa.
PubMed:
Anti-platelet effect of the constituents isolated from the barks and fruits of Magnolia obovata.
PubMed:
Antiproliferative constituents in the plants 7. Leaves of Clerodendron bungei and leaves and bark of C. trichotomum.
PubMed:
Studies on the hepatocyte protective activity and the structure-activity relationships of quinic acid and caffeic acid derivatives from the flower buds of Lonicera bournei.
PubMed:
Inhibitory effect of Perilla frutescens and its phenolic constituents on cultured murine mesangial cell proliferation.
PubMed:
Purification and characterization of a novel esterase induced by growth of Aspergillus niger on sugar-beet pulp.
PubMed:
Phenolic compounds from Duchesnea chrysantha and their cytotoxic activities in human cancer cell.
PubMed:
Inhibitory effect of caffeic acid esters on azoxymethane-induced biochemical changes and aberrant crypt foci formation in rat colon.
PubMed:
Effect of caffeic acid esters on carcinogen-induced mutagenicity and human colon adenocarcinoma cell growth.
PubMed:
Inhibition of platelet activation and endothelial cell injury by polyphenolic compounds isolated from Lonicera japonica Thunb.
PubMed:
Studies on non-sesquiterpenoid constituents of Gaillardia pulchella. II. Less lipophilic substances, methyl caffeate as an antitumor catecholic.