meta-coumaric acid
3-hydroxycinnamic acid
 
Notes:
Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. (Wikipedia)
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CAS Number: 588-30-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 209-615-0
FDA UNII: KWJ2DDJ34H
Beilstein Number: 2690254
MDL: MFCD00004390
XlogP3: 1.80 (est)
Molecular Weight: 164.16036000
Formula: C9 H8 O3
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
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Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 373.00 to  374.00 °C. @ 760.00 mm Hg (est)
Flash Point: 381.00 °F. TCC ( 193.70 °C. ) (est)
logP (o/w): 0.928 (est)
Soluble in:
 water, 2.709e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Sigma-Aldrich
For experimental / research use only.
m-Coumaric Acid
analytical standard
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Safety Information:
 
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
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for meta-coumaric acid usage levels up to:
 not for fragrance use.
 
Recommendation for meta-coumaric acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 11496
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 3-(3-hydroxyphenyl)prop-2-enoic acid
Chemidplus: 0000588307
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References:
 3-(3-hydroxyphenyl)prop-2-enoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 11496
Pubchem (sid): 134976365
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (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
Golm Metabolome Database: Search
Metabolomics Database: Search
KEGG (GenomeNet): C12621
HMDB (The Human Metabolome Database): HMDB01713
FooDB: FDB002590
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 bilberry fruit
Search Trop  Picture
 bilberry fruit juice
Search Trop  Picture
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Synonyms:
 cinnamic acid, m-hydroxy-
3-coumaric acid
m-coumaric acid
3-hydroxycinnamic acid
m-hydroxycinnamic acid
meta-hydroxycinnamic acid
3-(3-hydroxyphenyl)-2-propenoic acid
3-(3-hydroxyphenyl)acrylic acid
3-(3-hydroxyphenyl)prop-2-enoic acid
2-propenoic acid, 3- (3-hydroxyphenyl)-
2-propenoic acid, 3-(3-hydroxyphenyl)-
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Articles:
PubMed: Catalytic activity of the two-component flavin-dependent monooxygenase from Pseudomonas aeruginosa toward cinnamic acid derivatives.
PubMed: Assessment of the anti-invasion potential and mechanism of select cinnamic acid derivatives on human lung adenocarcinoma cells.
PubMed: Antimicrobial activity of phenolic compounds identified in wild mushrooms, SAR analysis and docking studies.
PubMed: Increasing antioxidant activity of procyanidin extracts from the pericarp of Litchi chinensis processing waste by two probiotic bacteria bioconversions.
PubMed: Design, synthesis and biological evaluation of ferulic Acid amides as selective matrix metalloproteinase inhibitors.
PubMed: Mesoporous silica SBA-15, a new adsorbent for bioactive polyphenols from red wine.
PubMed: Characterization of hydroxycinnamic acid derivatives binding to bovine serum albumin.
PubMed: Energetics and structural properties, in the gas phase, of trans-hydroxycinnamic acids.
PubMed: A fast method using a new hydrophilic-lipophilic balanced sorbent in combination with ultra-high performance liquid chromatography for quantification of significant bioactive metabolites in wines.
PubMed: Antimicrobial activity and phenolic content of natural site and micropropagated Limonium avei (De Not.) Brullo & Erben plant extracts.
PubMed: The proglycation effect of caffeic acid leads to the elevation of oxidative stress and inflammation in monocytes, macrophages and vascular endothelial cells.
PubMed: Spectroscopic implications of the electron donor-acceptor effect in the photoactive yellow protein chromophore.
PubMed: Chemical composition of Solanum nigrum linn extract and induction of autophagy by leaf water extract and its major flavonoids in AU565 breast cancer cells.
PubMed: [Systematic review on sodium ferulate for treatment of diabetic nephropathy].
PubMed: New CE-ESI-MS analytical method for the separation, identification and quantification of seven phenolic acids including three isomer compounds in virgin olive oil.
PubMed: Mass spectrometric investigations of alpha- and beta-cyclodextrin complexes with ortho-, meta- and para-coumaric acids by negative mode electrospray ionization.
PubMed: Phenolic acid nanoparticle formation in iron-containing aqueous solutions.
PubMed: Chlorogenic acid and its metabolite m-coumaric acid evoke neurite outgrowth in hippocampal neuronal cells.
PubMed: Reversed phase-HPLC for rapid determination of polyphenols in flowers of rose species.
PubMed: Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics.
PubMed: In vitro antioxidant activity of coffee compounds and their metabolites.
PubMed: Urinary excretion of 13 dietary flavonoids and phenolic acids in free-living healthy subjects - variability and possible use as biomarkers of polyphenol intake.
PubMed: Catalytic activity, duplication and evolution of the CYP98 cytochrome P450 family in wheat.
PubMed: Non-natural cinnamic acid derivatives as substrates of cinnamate 4-hydroxylase.
PubMed: Highly efficient preparation of lipophilic hydroxycinnamates by solvent-free lipase-catalyzed transesterification.
PubMed: Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods.
PubMed: Targeting antioxidative signal transduction and stress response system: control of pathogenic Aspergillus with phenolics that inhibit mitochondrial function.
PubMed: Inhibitory effect of phenolic acids on the proliferation of 3T3-L1 preadipocytes in relation to their antioxidant activity.
PubMed: The feruloyl esterase system of Talaromyces stipitatus: determining the hydrolytic and synthetic specificity of TsFaeC.
PubMed: Isolation and characterization of Halomonas sp. strain IMPC, a p-coumaric acid-metabolizing bacterium that decarboxylates other cinnamic acids under hypersaline conditions.
PubMed: A coumaroyl-ester-3-hydroxylase insertion mutant reveals the existence of nonredundant meta-hydroxylation pathways and essential roles for phenolic precursors in cell expansion and plant growth.
PubMed: Determination of hydrogen peroxide scavenging activity of cinnamic and benzoic acids employing a highly sensitive peroxyoxalate chemiluminescence-based assay: structure-activity relationships.
PubMed: Phenolic acid profiles in some small berries.
PubMed: Identification of phenolics for control of Aspergillus flavus using Saccharomyces cerevisiae in a model target-gene bioassay.
PubMed: Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers.
PubMed: Absorption, metabolism, degradation and urinary excretion of rosmarinic acid after intake of Perilla frutescens extract in humans.
PubMed: Synergistic effect of antioxidant phenolic acids on human phenolsulfotransferase activity.
PubMed: Orally administered rosmarinic acid is present as the conjugated and/or methylated forms in plasma, and is degraded and metabolized to conjugated forms of caffeic acid, ferulic acid and m-coumaric acid.
PubMed: Transepithelial transport of chlorogenic acid, caffeic acid, and their colonic metabolites in intestinal caco-2 cell monolayers.
PubMed: Structural effects of phenolic acids on the transepithelial transport of fluorescein in caco-2 cell monolayers.
PubMed: Identification of metabolites of (-)-epicatechin gallate and their metabolic fate in the rat.
PubMed: Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats.
PubMed: Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity.
PubMed: Differential production of meta hydroxylated phenylpropanoids in sweet basil peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases.
PubMed: Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection.
PubMed: Algal growth inhibition effects and inducement modes by plant-producing phenols.
PubMed: Metabolites of orally administered Perilla frutescens extract in rats and humans.
PubMed: Genetic organization and characteristics of the 3-(3-hydroxyphenyl)propionic acid degradation pathway of Comamonas testosteroni TA441.
PubMed: Metabolism of rosmarinic acid in rats.
PubMed: Inhibition of peroxynitrite dependent tyrosine nitration by hydroxycinnamates: nitration or electron donation?
PubMed: A 3-(3-hydroxyphenyl)propionic acid catabolic pathway in Rhodococcus globerulus PWD1: cloning and characterization of the hpp operon.
PubMed: Genetic characterization and expression in heterologous hosts of the 3-(3-hydroxyphenyl)propionate catabolic pathway of Escherichia coli K-12.
PubMed: Properties of a Maize Glutathione S-Transferase That Conjugates Coumaric Acid and Other Phenylpropanoids.
PubMed: Structure-activity relationship of caffeic acid analogues on xanthine oxidase inhibition.
PubMed: The blocking effect of phenolic acid on N-nitrosomorpholine formation in vitro.
PubMed: Allelopathic compounds in leaves ofGliricidia sepium (Jacq.) kunth ex walp. and its effect onSorghum vulgare L.
PubMed: Characterization of bispecific caffeic acid/5-hydroxyferulic acid O-methyltransferase from aspen.
PubMed: Purification and characterization of p-coumaroyl-D-glucose hydroxylase of sweet potato (Ipomoea batatas) roots.
PubMed: Antimicrobial activity and inhibition of aflatoxin B1 formation by olive plant tissue constituents.
PubMed: Kinetic study on the slow inhibition of epidermis tyrosinase by m-coumaric acid.
PubMed: [Biliary excretion of choleretically active cinnamic acid derivatives in the rat].
PubMed: 9,10-Dihydrophenanthrenes as phytoalexins of Orchidaceae. Biosynthetic studies in vitro and in vivo proving the route from L-phenylalanine to dihydro-m-coumaric acid, dihydrostilbene and dihydrophenanthrenes.
PubMed: Short-term inhibition of fatty acid biosynthesis in isolated hepatocytes by mono-aromatic compounds.
PubMed: Enzymatic hydroxylation of m-coumaric acid by mice liver hydroxylase.
PubMed: Biosynthesis of phytoquinones. Biosynthetic origins of the nuclei and satellite methyl groups of plastoquinone, tocopherols and tocopherolquinones in maize shoots, bean shoots and ivy leaves.
PubMed: Degradation of phenylalanine and tyrosine by Sporobolomyces roseus.
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