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methyl caffeate
2-propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester, (2E)-

Supplier Sponsors

Name:methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CAS Number: 3843-74-1Picture of molecule3D/inchi
FDA UNII:N79173B9HF
Nikkaji Web:J46.681F
MDL:MFCD00210468
XlogP3:1.50 (est)
Molecular Weight:194.18650000
Formula:C10 H10 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Caffeic acid methyl ester >98%
TCI AMERICA
For experimental / research use only.
Methyl Caffeate >98.0%(GC)(T)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
Env. Mutagen Info. Center:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :689075
National Institute of Allergy and Infectious Diseases:Data
methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Chemidplus:0003843741
 
References:
 methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):689075
Pubchem (sid):135049479
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10477
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 gaillardia pulchella
Search Trop Picture
 
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)-
 

Articles:

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.
 
Notes:
from plant gaillardia pulchella.
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