EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

ortho-coumaric acid
2-hydroxycinnamic acid

Supplier Sponsors

Name:3-(2-hydroxyphenyl)prop-2-enoic acid
CAS Number: 583-17-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:209-500-5
FDA UNII: 2S0H1PX3LM
Beilstein Number:2207352
XlogP3:1.50 (est)
Molecular Weight:164.16036000
Formula:C9 H8 O3
NMR Predictor:Predict (works with chrome, Edge 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: 348.00 to 349.00 °C. @ 760.00 mm Hg (est)
Flash Point: 353.00 °F. TCC ( 178.50 °C. ) (est)
logP (o/w): 1.021 (est)
Soluble in:
 water, 2.709e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
2-hydroxycinnamic acid 95%
WEN International
2-Hydroxycinnamic Acid, Natural
 
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
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for ortho-coumaric acid usage levels up to:
 not for fragrance use.
 
Recommendation for ortho-coumaric acid flavor usage levels up to:
 not for flavor use.
 
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 :11968
National Institute of Allergy and Infectious Diseases:Data
3-(2-hydroxyphenyl)prop-2-enoic acid
Chemidplus:0000583175
 
References:
 3-(2-hydroxyphenyl)prop-2-enoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):11968
Pubchem (sid):135048764
 
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
KEGG (GenomeNet):C01772
HMDB (The Human Metabolome Database):HMDB02641
FooDB:FDB011258
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 barley seed
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 bilberry fruit
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 bilberry fruit juice
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 chamomile sweet false chamomile plant
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 cherry sweet cherry
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 coffee
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 currant black currant fruit
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 evening-primrose plant
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 fennel seed
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 olive fruit
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 oregano leaf
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 pea seed
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 peanut nut
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 sesame fruit
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 sesame leaf
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 soybean seed
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 turmeric leaf
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 wheat seed
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Synonyms:
2-coumaric acid
o-coumaric acid
2-hydroxycinnamic acid
3-(2-hydroxyphenyl)-2-propenoic acid
3-(2-hydroxyphenyl)acrylic acid
3-(2-hydroxyphenyl)prop-2-enoic acid
2-propenoic acid, 3-(2-hydroxyphenyl)-
 

Articles:

US Patents:6,096,918 - Aryl-acrylic acid esters
PubMed:Experimental designs characterizing seasonal variations and solvent effects on the quantities of coumarin and related metabolites from Mikania laevigata.
PubMed:A drag reducing surfactant threadlike micelle system with unusual rheological responses to pH.
PubMed:Anticarcinogenic effect and carcinogenic potential of the dietary phenolic acid: o-coumaric acid.
PubMed:Phenolics from Ageratina adenophora roots and their phytotoxic effects on Arabidopsis thaliana seed germination and seedling growth.
PubMed:Catalytic activity of the two-component flavin-dependent monooxygenase from Pseudomonas aeruginosa toward cinnamic acid derivatives.
PubMed:Effects of molecular structure of polyphenols on their noncovalent interactions with oat β-glucan.
PubMed:Seasonal variation on the contents of coumarin and kaurane-type diterpenes in Mikania laevigata and M. glomerata leaves under different shade levels.
PubMed:Bioactive microconstituents and antioxidant properties of wild edible mushrooms from the island of Lesvos, Greece.
PubMed:Bilirubin clearance and antioxidant activities of ethanol extract of Phyllanthus amarus root in phenylhydrazine-induced neonatal jaundice in mice.
PubMed:Simultaneous determination of anthocyanins, coumarins and phenolic acids in fruits, kernels and liqueur of Prunus mahaleb L.
PubMed:Energetics and structural properties, in the gas phase, of trans-hydroxycinnamic acids.
PubMed:Development of a novel microextraction by packed sorbent-based approach followed by ultrahigh pressure liquid chromatography as a powerful technique for quantification phenolic constituents of biological interest in wines.
PubMed:Degradations of model compounds representing some phenolics in olive mill wastewater via electro-Fenton and photoelectro-Fenton treatments.
PubMed:Development and validation of two methods based on high-performance liquid chromatography-tandem mass spectrometry for determining 1,2-benzopyrone, dihydrocoumarin, o-coumaric acid, syringaldehyde and kaurenoic acid in guaco extracts and pharmaceutical preparations.
PubMed:Uncommonly high levels of 3-deoxyanthocyanidins and antioxidant capacity in the leaf sheaths of dye sorghum.
PubMed:Polyphenolics profile, antioxidant and radical scavenging activity of leaves and stem of Raphanus sativus L.
PubMed:Transport and metabolism of the antitumour drug candidate 2'-benzoyloxycinnamaldehyde in Caco-2 cells.
PubMed:A novel 4-hydroxycoumarin biosynthetic pathway.
PubMed:Effect of maturity stages and drying methods on the retention of selected nutrients and phytochemicals in bitter melon (Momordica charantia) leaf.
PubMed:Identification and quantification of flavonoids and phenolic acids in burr parsley (Caucalis platycarpos L.), using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry.
PubMed:Synergy effect of sodium acetate and glycosidically bound volatiles on the release of volatile compounds from the unscented cut flower (Delphinium elatum L. "Blue Bird").
PubMed:Plasma pharmacokinetics and metabolism of the antitumour drug candidate 2'-benzoyloxycinnamaldehyde in rats.
PubMed:Decaying signals: will understanding bacterial-plant communications lead to control of soft rot?
PubMed:Phenolic compounds rutin and o-coumaric acid ameliorate obesity induced by high-fat diet in rats.
PubMed:Novel photosystem involving protonation and deprotonation processes modelled on a PYP photocycle.
PubMed:Type III secretion system genes of Dickeya dadantii 3937 are induced by plant phenolic acids.
PubMed:Development of micromarkers with various photoluminescence colors as tracers for shadowing pursuits.
PubMed:Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics.
PubMed:Effects of flavonoids and phenolic acids on the inhibition of adipogenesis in 3T3-L1 adipocytes.
PubMed:Degradation of indulin, a kraft pine lignin, by Serratia marcescens.
PubMed:Effect of molecular structure of phenolic families as hydroxycinnamic acids and catechins on their antioxidant effectiveness in minced fish muscle.
PubMed:High-amylose corn exhibits better antioxidant activity than typical and waxy genotypes.
PubMed:Single-drop microextraction followed by in-syringe derivatization and gas chromatography-mass spectrometric detection for determination of organic acids in fruits and fruit juices.
PubMed:Inhibitory effect of phenolic acids on the proliferation of 3T3-L1 preadipocytes in relation to their antioxidant activity.
PubMed:LC characterisation of guaco medicinal extracts, Mikania laevigata and M. glomerata, and their effects on allergic pneumonitis.
PubMed:Some aspects of physico-chemical properties of TiO2 nanocolloids with respect to their age, size, and structure.
PubMed:Free radical scavenging properties and phenolic content of Chinese black-grained wheat.
PubMed:Effect of phenols on natural killer (NK) cell-mediated death in the K562 human leukemic cell line.
PubMed:Comparison of antioxidant activity, anthocyanins, carotenoids, and phenolics of three native fresh and sun-dried date (Phoenix dactylifera L.) varieties grown in Oman.
PubMed:Phenolic acid profiles in some small berries.
PubMed:Effect of far-infrared irradiation on the antioxidant activity of defatted sesame meal extracts.
PubMed:Phenolic constituents from Ephedra nebrodensis.
PubMed:Identification of phenolics for control of Aspergillus flavus using Saccharomyces cerevisiae in a model target-gene bioassay.
PubMed:Synergistic effect of antioxidant phenolic acids on human phenolsulfotransferase activity.
PubMed:High-performance liquid chromatographic analysis of secoisolariciresinol diglucoside and hydroxycinnamic acid glucosides in flaxseed by alkaline extraction.
PubMed:In vitro cytotoxicity to human cells in culture of some phenolics from olive oil.
PubMed:Metabolic profiling of root exudates of Arabidopsis thaliana.
PubMed:Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity.
PubMed:Determination of available phenolic compounds in soils by liquid chromatography with solid-phase extraction.
PubMed:Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection.
PubMed:Comparative analysis of phenolic acids in mistletoe plants from various hosts.
PubMed:Effect of natural phenolic acids on DNA oxidation in vitro.
PubMed:Metabolism of phenolic compounds during loquat fruit development.
PubMed:A reevaluation of the peroxynitrite scavenging activity of some dietary phenolics.
PubMed:Antioxidant activity of 3,4-DHPEA-EA and protocatechuic acid: a comparative assessment with other olive oil biophenols.
PubMed:Singlet oxygen quenching and the redox properties of hydroxycinnamic acids.
PubMed:Metabolism and toxicity of coumarin on cultured human, rat, mouse and rabbit hepatocytes.
PubMed:HPLC analysis of tonka bean extracts.
PubMed:Properties of a Maize Glutathione S-Transferase That Conjugates Coumaric Acid and Other Phenylpropanoids.
PubMed:Metabolism of [3-14C] coumarin by human liver microsomes.
PubMed:Induction of Benzoic Acid 2-Hydroxylase in Virus-Inoculated Tobacco.
PubMed:Pathway of Salicylic Acid Biosynthesis in Healthy and Virus-Inoculated Tobacco.
PubMed:Allelopathic compounds in leaves ofGliricidia sepium (Jacq.) kunth ex walp. and its effect onSorghum vulgare L.
PubMed:Purification and characterization of p-coumaroyl-D-glucose hydroxylase of sweet potato (Ipomoea batatas) roots.
PubMed:[Value of determining the activity of cholesterol esterase in the duodenal contents].
PubMed:[Assessment of cholesterol esterase activity in the duodenal contents of man].
PubMed:Antimicrobial activity and inhibition of aflatoxin B1 formation by olive plant tissue constituents.
PubMed:Partial purification and characterization of UDPG:t-cinnamate glucosyltransferase in the root of sweet potato, Ipomoea batatas Lam.
PubMed:Subcellular Localization of 2-(beta-d-Glucosyloxy)-Cinnamic Acids and the Related beta-glucosidase in Leaves of Melilotus alba Desr.
PubMed:Intracellular Localization of Two Enzymes Involved in Coumarin Biosynthesis in Melilotus alba.
PubMed:Regulation of L-phenylalanine ammonia-lyase from Rhizoctonia solani.
PubMed:Formation of p-coumaric acid and o-coumaric acid from L-phenylalanine by microsomal membrane fractions from potato: Evidence of membrane-bound enzyme complexes.
PubMed:On the metabolism of cinnamic acid in Cestrum poepigii: identification of o-coumaric acid and an o-coumaroylquinic acid.
PubMed:The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius.
PubMed:A proposed mechanism for the conversion of o-coumaric acid to 4-hydroxy-coumarin in Aspergillus fumigatus fresenius.
PubMed:Degradation of phenylalanine and tyrosine by Sporobolomyces roseus.
PubMed:Conversion of o-coumaric acid to 4-hydroxycoumarin by Fusarium sp.
PubMed:The biosynthesis of dicoumarol.
PubMed:METABOLISM OF COUMARIN BY A MICRO-ORGANISM: O-COUMARIC ACID AS AN INTERMEDIATE BETWEEN COUMARIN AND MELILOTIC ACID.
PubMed:THE METABOLISM OF COUMARIN BY A MICROORGANISM. II. THE REDUCTION OF O-COUMARIC ACID TO MELILOTIC ACID.
PubMed:Synthesis and antifungal activity of anilides of salicylic acid and o-coumaric acid.
PubMed:The metabolism of aromatic compounds in higher plants. I. Coumarin and o-coumaric acid.
PubMed:Studies in detoxication. 72. The metabolism of coumarin and of o-coumaric acid.
PubMed:The hydroxylation of coumarin and the cyclization of o-coumaric acid in vivo.
 
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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