ortho-coumaric acid

2-hydroxycinnamic acid

CAS: 583-17-5 C9 H8 O3 MW: 164.16036000

Identification

Nameortho-coumaric acid
IUPAC3-(2-hydroxyphenyl)prop-2-enoic acid
CAS Number583-17-5
EINECS209-500-5
FDA UNII2S0H1PX3LM
Molecular FormulaC9 H8 O3
Molecular Weight164.16036000
Beilstein2207352
XlogP31.50 (est)

Regulatory

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)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for ortho-coumaric acid usage levels up tonot for fragrance use.
Recommendation for ortho-coumaric acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

barley seed bilberry fruit bilberry fruit juice chamomile sweet false chamomile plant cherry sweet cherry coffee PMC currant black currant fruit evening-primrose plant fennel seed olive fruit oregano leaf pea seed peanut nut sesame fruit sesame leaf soybean seed turmeric leaf wheat seed

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)- 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.