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(E)-cinnamic acid

Chemical Structure

General Material Information

Preferred name (E)-cinnamic acid
Trivial Name trans-Cinnamic acid
Short Description trans-3-phenyl-2-propenoic acid
Formula C9 H8 O2
CAS Number 140-10-3
FEMA Number 2288
ECHA Number 205-398-1
FDA UNII U14A832J8D
Nikkaji Number J2.024I
Beilstein Number 1905952
MDL MFCD00004369
COE Number 22
Bio Activity Summary External link
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
Synonyms
  • (E)- benzene propenoic acid
  • (E)- benzylidene acetic acid
  • (E)- cinnamic acid natural
  • (E)- cinnamylic acid
  • (E)-3-phenyl acrylic acid
  • (E)-3-phenyl propenoic acid
  • (2E)-2-phenyl-2-propenoate
  • (2E)-3-phenyl-2-propenoate
  • (2E)-2-phenyl-2-propenoic acid
  • (2E)-3-phenyl-2-propenoic acid
  • (E)-3-phenyl-2-propenoic acid
  • trans-3-phenyl-2-propenoic acid
  • (2E)-3-phenylacrylic acid
  • (E)-3-phenylacrylic acid
  • (2E)-3-phenylprop-2-enoic acid
  • (E)-3-phenylprop-2-enoic acid
  • 2-propenoic acid, 3-phenyl-, (2E)-
  • 2-propenoic acid, 3-phenyl-, (E)-
  • 2-Propenoic acid, 3-phenyl-, (2E)-
  • Cinnamic acid, (E)-
  • 2-Propenoic acid, 3-phenyl-, (E)-
  • (2E)-3-Phenyl-2-propenoic acid
  • trans-Cinnamic acid
  • trans-β-Carboxystyrene
  • trans-3-Phenylacrylic acid
  • trans-3-Phenyl-2-propenoic acid
  • (E)-3-Phenylprop-2-enoic acid
  • (E)-3-Phenylacrylic acid
  • NSC 44010
  • (2E)-2-Phenyl-2-propenoic acid
  • (2E)-Cinnamic acid
  • 3-Phenyl-(E)-2-propenoic acid
  • (E)-3-Phenyl-2-propenoic acid
  • (2E)-3-Phenylprop-2-enoic acid

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Literature & References

(E)-3-phenylprop-2-enoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:140-10-3
Pubchem (cid):444539
Pubchem (sid):134974596
Flavornet:140-10-3
Publications by PubMed
Structural Investigations into the Stereochemistry and Activity of a Phenylalanine-2,3-Aminomutase from Taxus chinensis.
Poly[μ5-{hydrogen bis-[(E)-cinnamato]}-caesium].
Single-dose, subcutaneous recombinant phenylalanine ammonia lyase conjugated with polyethylene glycol in adult patients with phenylketonuria: an open-label, multicentre, phase 1 dose-escalation trial.
Chemical composition of essential oils from four Vietnamese species of piper (piperaceae).
Two new compounds from Aconitum tanguticum.
Phenylalanine Ammonia Lyase Catalyzed Synthesis of Amino Acids by an MIO-Cofactor Independent Pathway.
Experimental FT-IR, Laser-Raman and DFT spectroscopic analysis of 2,3,4,5,6-Pentafluoro-trans-cinnamic acid.
Trans-cinnamic acid increases adiponectin and the phosphorylation of AMP-activated protein kinase through G-protein-coupled receptor signaling in 3T3-L1 adipocytes.
Molecular cloning and yeast expression of cinnamate 4-hydroxylase from Ornithogalum saundersiae baker.
2,3,4,5,6-Penta-fluoro-trans-cinnamic acid.
[Chemical constituents from flower buds of Lonicera japonica].
Formation of complex natural flavours by biotransformation of apple pomace with basidiomycetes.
Synthesis, antimicrobial and cytotoxic activities of sulfonamidomethane linked heterocycles.
Cloning and mRNA expression analysis of the gene encoding phenylalanine ammonia-lyase of the ectomycorrhizal fungus Tricholoma matsutake.
Biotechnological production and applications of microbial phenylalanine ammonia lyase: a recent review.
Characterization of phenolic constituents from ephedra herb extract.
In vitro inhibition of canine distemper virus by flavonoids and phenolic acids: implications of structural differences for antiviral design.
Binuclear and chain-structure zinc(II) complexes constructed from 3,4-dimethoxy-trans-cinnamic acid and N-donor coligands 4-(1H-pyrazol-3-yl)pyridine and 4,4'-bipyridine.
Molecular mechanism depressing PMA-induced invasive behaviors in human lung adenocarcinoma cells by cis- and trans-cinnamic acid.
Effect of l-phenylalanine on PAL activity and production of naphthoquinone pigments in suspension cultures of Arnebia euchroma (Royle) Johnst.
Phenylalanine ammonia lyase (PAL) enzyme activity and antioxidant properties of some cyanobacteria isolates.
Characterization of cytochrome P450 monooxygenases isolated from trichome enriched fraction of Artemisia annua L. leaf.
[Chemical constituents of Phymatopteris hastate and their antioxidant activity].
The phenylalanine ammonia lyase (PAL) gene family shows a gymnosperm-specific lineage.
Metabolic profiling of glucosinolates, anthocyanins, carotenoids, and other secondary metabolites in kohlrabi (Brassica oleracea var. gongylodes).
Novel cinnamic acid/4-aminoquinoline conjugates bearing non-proteinogenic amino acids: towards the development of potential dual action antimalarials.
Bio-inspired catechol chemistry for electrophoretic nanotechnology of oxide films.
Contribution of CoA ligases to benzenoid biosynthesis in petunia flowers.
Evaluation of food protective property of five natural products using fresh-cut apple slice model.
Vibrational spectroscopic investigation of polymorphs and cocrystals of indomethacin.
[Molecular cloning and prokaryotic expression of phenylalanine ammonia-lyase gene FdPAL from Fagopyrum dibotrys].
Energetics and structural properties, in the gas phase, of trans-hydroxycinnamic acids.
Purification and characterization of antibacterial compounds of Pseudoalteromonas flavipulchra JG1.
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of leukemia and cancer cell lines.
A comparative study on the effectiveness of cis- and trans-form of cinnamic acid treatments for inhibiting invasive activity of human lung adenocarcinoma cells.
Paniculacin, a new coumarin derivative from Murraya paniculata.
[Chemical constituents from roots of Andrographis paniculata].
[Effect of nitrogen, phosphorus and potassium deficiency on content of phenolic compounds in exudation of American ginseng].
Hepatoprotective effects of lychee (Litchi chinensis Sonn.): a combination of antioxidant and anti-apoptotic activities.
Transformation of cinnamic acid from trans- to cis-form raises a notable bactericidal and synergistic activity against multiple-drug resistant Mycobacterium tuberculosis.
Single crystal to single crystal topochemical photoreactions: measuring the degree of disorder in the [2+2] photodimerization of trans-cinnamic acid using single-crystal 13C NMR spectroscopy.
Contact and fumigant toxicity of cinnamaldehyde and cinnamic acid and related compounds to Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
Automatic flow methodology for kinetic and inhibition studies of reactions with poorly water-soluble substrates in ionic liquid systems.
Fumigant toxicity of cassia and cinnamon oils and cinnamaldehyde and structurally related compounds to Dermanyssus gallinae (Acari: Dermanyssidae).
Cis-cinnamic acid-enhanced 1 gene plays a role in regulation of Arabidopsis bolting.
Application of twin screw extrusion in the manufacture of cocrystals, part I: four case studies.
Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A).
In vitro assessment of the antiviral potential of trans-cinnamic acid, quercetin and morin against equid herpesvirus 1.
Mutational analysis of phenylalanine ammonia lyase to improve reactions rates for various substrates.
Application of PET deprotection for orthogonal photocontrol of aqueous solution viscosity.
Sheep scab control using trans-cinnamic acid.
Constituents from Cistus salvifolius (Cistaceae) activate peroxisome proliferator-activated receptor-γ but not -δ and stimulate glucose uptake by adipocytes.
Partitioning of new carbon as ¹¹C in Nicotiana tabacum reveals insight into methyl jasmonate induced changes in metabolism.
Infection processes and involvement of defense-related genes in the expression of resistance in cultivars of subterranean clover (Trifolium subterraneum) to Phytophthora clandestina.
Selective trans-cinnamic acid uptake impairs [Ca2+]cyt homeostasis and growth in Cucumis sativus L.
trans-Pyridyl and naphthyridyl cinnamides as alternatives for urea in complexation of carboxylic acid and formation of water-templated assemblies in the solid state.
Structural determination of abutilins A and B, new flavonoids from Abutilon pakistanicum, by 1D and 2D NMR spectroscopy.
Size effects of aromatic substitution in the ortho position on the photodimerization kinetics of alpha-trans cinnamic acid derivatives. A solid-state NMR study.
[Chemical constituents of fresh celery].
Bioreactor production of secondary metabolites from cell cultures of periwinkle and sandalwood.
Identification of the constituents of balsam of peru in tomatoes.
Isoflavones, Flavan-3-ols, phenolic acids, total phenolic profiles, and antioxidant capacities of soy milk as affected by ultrahigh-temperature and traditional processing methods.
Conferols A and B, new anti-inflammatory 4-hydroxyisoflavones from Caragana conferta.
Trans-cinnamic acid and coumarin-3-carboxylic acid: experimental charge-density studies to shed light on [2 + 2] cycloaddition reactions.
[Studies on chemical constituents in roots and rhizomes of Notopterygium incisum].
Kinetics of the single-crystal to single-crystal two-photon photodimerization of alpha-trans-cinnamic acid to alpha-truxillic acid.
The main chemical composition and in vitro antifungal activity of the essential oils of Ocimum basilicum Linn. var. pilosum (Willd.) Benth.
Measuring aromaticity with the dimethyldihydropyrene ring current probe. Experimental and computational studies of the fulvenes and the strongly antiaromatic cyclopentadienone reveal large Mills-Nixon-type bond localization effects. Synthesis of fulvene-fused dihydropyrenes.
Enzymatic synthesis of enantiopure alpha- and beta-amino acids by phenylalanine aminomutase-catalysed amination of cinnamic acid derivatives.
Potential to reduce Escherichia coli shedding in cattle feces by using sainfoin (Onobrychis viciifolia) forage, tested in vitro and in vivo.
Screening of natural phenolic compounds for potential to inhibit bacterial cell division protein FtsZ.
The ornamental variety, Japanese striped corn, contains high anthocyanin levels and PAL specific activity: establishing the potential for development of an oral therapeutic.
[Studies on chemical constituents from stems and leaves of Jasminum lanceolarium].
Retention of phenylalanine ammonia-lyase activity in wheat seedlings during storage and in vitro digestion.
Novel inhibitors of beta-ketoacyl-ACP reductase from Escherichia coli.
Characterization of a phenylacetate-CoA ligase from Penicillium chrysogenum.
Temperature stability and photodimerization kinetics of beta-cinnamic acid and comparison to its alpha-polymorph as studied by solid-state NMR spectroscopy techniques and DFT calculations.
An unexpected phase transition during the [2 + 2] photocycloaddition reaction of cinnamic acid to truxillic acid: changes in polymorphism monitored by solid-state NMR.
Characterization of phenolic substances and antioxidant properties of food soybeans grown in the North Dakota-Minnesota region.
Total phenolics, phenolic acids, isoflavones, and anthocyanins and antioxidant properties of yellow and black soybeans as affected by thermal processing.
[Studies on chemical constituents and volatile oil of Xiaochengqi decoction].
Molecular cloning, expression and characterization of a phenylalanine ammonia-lyase gene (SmPAL1) from Salvia miltiorrhiza.
Biosynthesis of 15NL-phenylalanine by phenylalanine ammonia-lyase from Rhodotorula glutinis.
Manganese (Mn2+)-dependent storage stabilization of Rhodotorula glutinis phenylalanine ammonia-lyase activity.
Transient states in [2 + 2] photodimerization of cinnamic acid: correlation of solid-state NMR and X-ray analysis.
Synthesis and antimycobacterial evaluation of new trans-cinnamic acid hydrazide derivatives.
Inhibition of histone-deacetylase activity by short-chain fatty acids and some polyphenol metabolites formed in the colon.
Natural maize phenolic acids for control of aflatoxigenic fungi on maize.
[Chemical constituents from aerial parts of Plumbago zeylanica Linn].
Novel agents in the management of Mycobacterium tuberculosis disease.
Implementation and validation of localized constant-time correlated spectroscopy (LCT-COSY) on a clinical 3T MRI scanner for investigation of muscle metabolism.
Simultaneous determination of four active constituents in the roots of Scrophularia buergeriana by HPLC-DAD and LC-ESI-MS.
A modern view of phenylalanine ammonia lyase.
Quantitation of phenylalanine and its trans-cinnamic, benzoic and hippuric acid metabolites in biological fluids in a single GC-MS analysis.
Recombinant Saccharomyces cerevisiae strain expressing a model cytochrome P450 in the rat digestive environment: viability and bioconversion activity.
Nematicidal Activity of Cassia and Cinnamon Oil Compounds and Related Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae).
Templating photodimerization of trans-cinnamic acid esters with a water-soluble Pd nanocage.
Production of p-hydroxycinnamic acid from glucose in Saccharomyces cerevisiae and Escherichia coli by expression of heterologous genes from plants and fungi.
Influence of glyphosate on flower morphogenesis and pigmentation in Petunia hybrida.
Use of whey protein beads as a new carrier system for recombinant yeasts in human digestive tract.
Flavonoids and cinnamic acid esters as inhibitors of fungal 17beta-hydroxysteroid dehydrogenase: a synthesis, QSAR and modelling study.
Control of Aspergillus growth and aflatoxin production using natural maize phytochemicals under different conditions of water activity.
Gastrointestinal absorption and urinary excretion of trans-cinnamic and p-coumaric acids in rats.
Solid-state photodimerization kinetics of alpha-trans-cinnamic acid to alpha-truxillic acid studied via solid-state NMR.
Aspects of the photodimerization mechanism of 2,4-dichlorocinnamic acid studied by kinetic photocrystallography.
Evidence for involvement of the phenylpropanoid pathway in the biosynthesis of the norlignan agatharesinol.
[Study on chemical constituents of Lagotis yunnanensis].
Effects of common forage phenolic acids on Escherichia coli O157:H7 viability in bovine feces.
Study of cis-cinnamic acid in Arabidopsis thaliana.
E-cinnamic acid derivatives and phenolics from Chilean strawberry fruits, Fragaria chiloensis ssp. chiloensis.
Phenylalanine ammonia lyase, enzyme substitution therapy for phenylketonuria, where are we now?
[Studies on the chemical constituents in herb of Mentha haplocalyx].
Anti-inflammatory activities of alpha-truxillic acid derivatives and their monomer components.
Purification and characterization of polyphenol oxidase from nettle (Urtica dioica L.) and inhibitory effects of some chemicals on enzyme activity.
The gene stlA encodes a phenylalanine ammonia-lyase that is involved in the production of a stilbene antibiotic in Photorhabdus luminescens TT01.
The complex problem of sensitive skin.
[Isolation and structure identification of chemical constituents from Viscum liquidambaricolum].
Effects of cryoprotectants on the viability and activity of freeze dried recombinant yeasts as novel oral drug delivery systems assessed by an artificial digestive system.
Biochemical characterization of a prokaryotic phenylalanine ammonia lyase.
Metabolic engineering of the phenylpropanoid pathway in Saccharomyces cerevisiae.
Plant growth inhibition by cis-cinnamoyl glucosides and cis-cinnamic acid.
Gas-solid reactions of single crystals: A study of the reaction of bromine with single crystals of trans-cinnamic acid and a range of its derivatives by infrared and Raman microspectroscopy.
Anthocyanins and glutathione S-transferase activities in response to low temperature and frost hardening in Vaccinium myrtillus (L.).
Quantitative determination of curcuminoids in Curcuma rhizomes and rapid differentiation of Curcuma domestica Val. and Curcuma xanthorrhiza Roxb. by capillary electrophoresis.
Photodimerization of the alpha'-polymorph of ortho-ethoxy-trans-cinnamic acid in the solid state. I. Monitoring the reaction at 293 K.
A new polymorph of ortho-ethoxy-trans-cinnamic acid: single-to-single-crystal phase transformation and mechanism.
Structure-activity relationships of trans-cinnamic acid derivatives on alpha-glucosidase inhibition.
Co-incorporation of heterologously expressed Arabidopsis cytochrome P450 and P450 reductase into soluble nanoscale lipid bilayers.
Marmenol: a 7-geranyloxycoumarin from the leaves of Aegle marmelos Corr.
Synergism of polygodial and trans-cinnamic acid on inhibition of root elongation in lettuce seedling growth bioassays.
Characterization of an anti-tuberculosis resin glycoside from the prairie medicinal plant Ipomoea leptophylla.
Phenolic constituents of shea (Vitellaria paradoxa) kernels.
Capillary electrophoresis-based profiling and quantitation of total salicylic acid and related phenolics for analysis of early signaling in Arabidopsis disease resistance.
Recombinant Saccharomyces cerevisiae expressing P450 in artificial digestive systems: a model for biodetoxication in the human digestive environment.
Metabolic profiling of root exudates of Arabidopsis thaliana.
Mechanisms of inhibition of phenylalanine ammonia-lyase by phenol inhibitors and phenol/glycine synergistic inhibitors.
Calmodulin inhibitors from Leucophyllum ambiguum.
First investigations of the kinetics of the topochemical reaction of p-formyl-trans-cinnamic acid by time-resolved X-ray diffraction.
[Expression in Lactococcus lactis of catalytically active phenylalanine ammonia-lyase from parsley].
Inhibitory activity of Cinnamomum cassia bark-derived component against rat lens aldose reductase.
The photodimerisation of the alpha- and beta-forms of trans-cinnamic acid: a study of single crystals by vibrational microspectroscopy.
Alterations in Taxol production in plant cell culture via manipulation of the phenylalanine ammonia lyase pathway.
Optimization of reaction conditions and stabilization of phenylalanine ammonia lyase-containing Rhodotorula glutinis cells during bioconversion of trans-cinnamic acid to L-phenylalanine.
Arabidopsis CYP98A3 mediating aromatic 3-hydroxylation. Developmental regulation of the gene, and expression in yeast.
Cloning and characterization of the abscisic acid-specific glucosyltransferase gene from adzuki bean seedlings.
Inactivation, complementation, and heterologous expression of encP, a novel bacterial phenylalanine ammonia-lyase gene.
Antifouling activity of six nontoxic chemicals on spore attachment of Ulva fasciata.
Synthesis and interaction with copper(II) cations of cyano- and aminoresorcin[4]arenes.
Genetically engineered Pseudomonas: a factory of new bioplastics with broad applications.
Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root.
Cloning and disruption of a phenylalanine ammonia-lyase gene from Ustilago maydis.
Simultaneous analysis of the di(2-ethylhexyl)phthalate metabolites 2-ethylhexanoic acid, 2-ethyl-3-hydroxyhexanoic acid and 2-ethyl-3-oxohexanoic acid in urine by gas chromatography-mass spectrometry.
Synthesis of styrenes through the biocatalytic decarboxylation of trans-cinnamic acids by plant cell cultures.
Evaluation of polyphenolic and flavonoid compounds in honeybee-collected pollen produced in Spain.
A comparative vibrational and NMR study of cis-cinnamic acid polymorphs and trans-cinnamic acid.
Simultaneous determination of quercetin, kaempferol and (E)-cinnamic acid in vegetative organs of Schisandra chinensis Baill. by HPLC.
Growth-Inhibiting Effects of Cinnamomum cassia Bark-Derived Materials on Human Intestinal Bacteria.
Free and conjugated benzoic acid in tobacco plants and cell cultures. Induced accumulation upon elicitation of defense responses and role as salicylic acid precursors.
New constituents from Gliricidia sepium.
The photodimerisation of trans-cinnamic acid and its derivatives: a study by vibrational microspectroscopy.
The crystal structure of the 1:1 complex of beta-cyclodextrin with trans-cinnamic acid.
Phenylalanine ammonia lyase production by gamma irradiated and analog-resistant mutants of Rhodotorula glutinis.
Molecular characterization of CYP73A9 and CYP82A1 P450 genes involved in plant defense in pea.
Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana.
Insecticidal and fumigant activities of Cinnamomum cassia bark-derived materials against Mechoris ursulus (Coleoptera: attelabidae).
Effect of pH on the stability of plant phenolic compounds.
Cloning and characterization of eight cytochrome P450 cDNAs from chickpea (Cicer arietinum L.) cell suspension cultures.
Novel scheme for biosynthesis of aryl metabolites from L-phenylalanine in the fungus Bjerkandera adusta.
Vacuolar transport of the glutathione conjugate of trans-cinnamic acid.
Stimulatory effect of trans-cinnamaldehyde on noradrenaline secretion in guinea-pig ileum myenteric nerve terminals.
Soybean peroxidase as an effective bromination catalyst*
Altering expression of cinnamic acid 4-hydroxylase in transgenic plants provides evidence for a feedback loop at the entry point into the phenylpropanoid pathway.
Tritium secondary kinetic isotope effect on phenylalanine ammonia-lyase-catalyzed reaction.
Transgene-mediated and elicitor-induced perturbation of metabolic channeling at the entry point into the phenylpropanoid pathway
Foliar modifications induced by inhibition of polar transport of auxin.
Role of unusual amino acid residues in the proximal and distal heme regions of a plant P450, CYP73A1.
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-(aminomethyl)-3-phenylbicyclo[2.2.2]- and -[2.2.1]alkane dopamine uptake inhibitors.
A different approach to treatment of phenylketonuria: phenylalanine degradation with recombinant phenylalanine ammonia lyase.
Influence of chemical treatments on glutathione S-transferases of maize with activity towards metolachlor and cinnamic acid.
Growth-inhibitory activities of benzofuran and chromene derivatives toward Tenebrio molitor.
Piperonylic acid, a selective, mechanism-based inactivator of the trans-cinnamate 4-hydroxylase: A new tool to control the flux of metabolites in the phenylpropanoid pathway
Synergistic activities of antituberculous drugs with cerulenin and trans-cinnamic acid against Mycobacterium tuberculosis.
Giardia intestinalis: characterization of a NADP-dependent glutamate dehydrogenase.
Metabolism of ferulic acid to vanillin. A bacterial gene of the enoyl-SCoA hydratase/isomerase superfamily encodes an enzyme for the hydration and cleavage of a hydroxycinnamic acid SCoA thioester.
Activity of L-phenylalanine ammonia-lyase in organic solvents.
Molecular cloning of 4-coumarate:coenzyme A ligase in loblolly pine and the roles of this enzyme in the biosynthesis of lignin in compression wood.
Studies on non-immune immediate contact reactions in an unselected population.
Sensitivity ofLemna bioassay interacts with stock-culture period.
Evidence for acetyl coenzyme A and cinnamoyl coenzyme A in the anaerobic toluene mineralization pathway in Azoarcus tolulyticus Tol-4.
Cloning of wound-induced cytochrome P450 monooxygenases expressed in pea.
Charge state distribution shifting of protein ions observed in matrix-assisted laser desorption ionization mass spectrometry.
Triterpenoid saponins from Mimosa pigra.
Biosynthesis of pseudoisoeugenols in tissue cultures of Pimpinella anisum. Phenylalanine ammonia lyase and cinnamic acid 4-hydroxylase activities.
Properties of a Maize Glutathione S-Transferase That Conjugates Coumaric Acid and Other Phenylpropanoids.
Biosynthesis and metabolism of salicylic acid.
Effects of reduced phenolic acids on metabolism of propionate and palmitate in bovine liver tissue in vitro.
Metabolism of trans-cinnamic acid in the rat and the mouse and its variation with dose.
Potential drug targets for Mycobacterium avium defined by radiometric drug-inhibitor combination techniques.
[Studies on the induction of L-phenylalanine ammonia lyase(PAL) in Rhodotorula glutinis and transformation of phenylalanine from trans-cinnamic acid].
Photoaffinity labeling of Arabidopsis thaliana plasma membrane vesicles by 5-azido-[7-3H]indole-3-acetic acid: identification of a glutathione S-transferase.
Ortho-anisic acid as internal standard for the simultaneous quantitation of salicylic acid and its putative biosynthetic precursors in cucumber leaves.
Pathway of Salicylic Acid Biosynthesis in Healthy and Virus-Inoculated Tobacco.
Interactions oftrans-cinnamic acid, its related phenolic allelochemicals, and abscisic acid in seedling growth and seed germination of lettuce.
Purification and characterization of a glutathione S-transferase from benoxacor-treated maize (Zea mays).
Auxin Polar Transport Is Essential for the Establishment of Bilateral Symmetry during Early Plant Embryogenesis.
Stress Responses in Alfalfa (Medicago sativa L.) (XIV. Changes in the Levels of Phenylpropanoid Pathway Intermediates in Relation to Regulation of L-Phenylalanine Ammonia-Lyase in Elicitor-Treated Cell-Suspension Cultures).
Expression of a Ripening-Related Avocado (Persea americana) Cytochrome P450 in Yeast.
Resin glycosides. XV. Simonins I-V, ether-soluble resin glycosides (jalapins) from the roots of Ipomoea batatas (cv. Simon).
Styrene Formation by the Decomposition by Pichia carsonii of trans-Cinnamic Acid Added to a Ground Fish Product.
Phenylpropanoid Metabolism in Suspension Cultures of Vanilla planifolia Andr. : IV. Induction of Vanillic Acid Formation.
Styrene formation by the decomposition by Pichia carsonii of trans-cinnamic acid added to a ground fish product.
Effect of fungal homogenate, enzyme inhibitors and osmotic stress on alkaloid content of Catharanthus roseus cell suspension cultures.
[A fluorometric method of determining cholesterol esterase activity].
Phenylpropanoid pathway intermediates regulate transient expression of a chalcone synthase gene promoter.
Multiple forms of NADPH-cytochrome P450 reductase in higher plants.
Effects of trans-Cinnamic Acid on Expression of the Bean Phenylalanine Ammonia-Lyase Gene Family.
Phenylpropanoid Metabolism in Suspension Cultures of Vanilla planifolia Andr. : III. Conversion of 4-Methoxycinnamic Acids into 4-Hydroxybenzoic Acids.
Antigenic Crossreactivity between Bacterial and Plant Cytochrome P-450 Monoxygenases.
Sodium-dependent L-lactate uptake by bovine intestinal brush border membrane vesicles.
Isolation and characterization of coumaphos-metabolizing bacteria from cattle dip.
New ester alkaloids from lupins (genus lupinus).
Strain Improvement of Rhodotorula graminis for Production of a Novel l-Phenylalanine Ammonia-Lyase.
Substrate specificity, regiospecificity and stereospecificity of halogenation reactions catalyzed by non-heme-type bromoperoxidase of Corallina pilulifera.
Bioconversion of trans-cinnamic acid to L-phenylalanine in an immobilized whole cell reactor.
Extracorporeal enzyme reactors for depletion of phenylalanine in phenylketonuria.
Production of l-Phenylalanine from Starch by Analog-Resistant Mutants of Bacillus polymyxa.
Comparison of in vitro bacterial bioluminescence and tissue culture bioassays and in vivo tests for evaluating acute toxicity of biomaterials.
Reversal of Abscisic Acid-Induced Stomatal Closure by trans-Cinnamic and p-Coumaric Acid.
An extracorporeal hollow-fiber reactor for phenylketonuria using immobilized phenylalanine ammonia lyase.
Chloroperoxidase-catalyzed halogenation of trans-cinnamic acid and its derivatives.
Metabolism of cinnamic, p-coumaric, and ferulic acids by Streptomyces setonii.
In vivo safety of hollow fiber enzyme-reactors with immobilized phenylalanine ammonia-lyase in a large animal model for phenylketonuria.
Antimutagenic effects of cinnamaldehyde on chemical mutagenesis in Escherichia coli.
Production of l-Phenylalanine from trans-Cinnamic Acid with Rhodotorula glutinis Containing l-Phenylalanine Ammonia-Lyase Activity.
Time Course of Induction of Cytochrome P-450, NADPH-Cytochrome c Reductase, and Cinnamic Acid Hydroxylase by Phenobarbital, Ethanol, Herbicides, and Manganese in Higher Plant Microsomes.
Inhibition of Aspergillus growth and aflatoxin release by derivatives of benzoic acid.
[Phenylalanine ammonia-lyase of pigmented yeasts].
Intracellular Localization of Two Enzymes Involved in Coumarin Biosynthesis in Melilotus alba.
trans-Cinnamic acid--alpha-cyclodextrin system as studied by solubility, spectral, and potentiometric techniques.
Mutagenicity of vinyl compounds in Salmonella typhimurium.
Solubilized auxin-binding protein : Subcellular localization and regulation by a soluble factor from homogenates of corn shoots.
[Biosynthesis of beta-phenylethanol in rose petals].
trans-Cinnamic acid 4-hydroxylase of Phaseolus mungo. A new assay method.
Preparation of immobilized L-phenylalanine ammonia-lyase in tubular form for depletion of L-phenylalanine.
Polarity of Production of Polyphenols and Development of Various Enzyme Activities in Cut-injured Sweet Potato Root Tissue.
Phenylketonuria: a new method for the simultaneous determination of plasma phenylalanine and tyrosine.
trans-Cinnamic acid as a mediator of the light-stimulated increase in hydroxycinnamoyl-CoA: quinate hydroxycinnamoyl transferase.
Biophysical and enzymological studies upon the interaction of trans-cinnamic acid with higher plant microsomal cytochromes P-450.
Synthesis of stereospecifically deuterated phenylalamines and determination of their configuration.
Phenylalanine ammonia-lyase. Induction and purification from yeast and clearance in mammals.
A spectrophotometric assay for trans-cinnamic acid 4-hydroxylase activity.
The 2-hydroxylation of trans-cinnamic acid by chloroplasts from Melilotus alba Desr.
Tannins as gibberellin antagonists.
Modification of the cytokinin promotion of deoxyisoflavone synthesis in soybean tissue.
Influence of side-chain substituents on the position of cleavage of the benzene ring by Pseudomonas fluorescens.
l-Phenylalanine Ammonia-Lyase Activity During Germination of Phaseolus vulgaris.
Effects of Culture Conditions on Production of trans-Cinnamic Acid from Alkylbenzenes by Soil Microorganisms.
Turnover and metabolism of chlorogenic Acid in xanthium leaves and potato tubers.

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):C00423
HMDB (The Human Metabolome Database):HMDB00930
FooDB:FDB008784
Export Tariff Code:2916.39.0600
VCF-Online:VCF Volatile Compounds in Food
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 148.16116333008
Melting Point 132 to 135°C @ 760 mm Hg
Boiling Point 295 to 305°C @ 760 mm Hg
Vapor Pressure 0.00471 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 2.13
Solubility
alcohol Yes
fixed oils Yes
water, 2911 mg/L @ 25 °C (est) Yes
water, 546 mg/L @ 25 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Balsamic
balsamic, sweet, storax
Odor strength low
Substantivity 340 hour(s) at 20.00 % in dipropylene glycol
General comment At 100.00 %. balsam sweet storax

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
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:
oral-bird - wild LD50 100 mg/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for (E)-cinnamic acid usage levels up to:
0.5000 % in the fragrance concentrate.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3. Update in publication number(s): 28
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 232.88000384.00000
beverages(nonalcoholic): 300.00000400.00000
beverages(alcoholic): 570.00000712.00000
breakfast cereal: --
cheese: --
chewing gum: 224.00000300.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: 746.000001000.00000
fish products: --
frozen dairy: 192.00000263.00000
fruit ices: --
gelatins / puddings: 459.00000500.00000
granulated sugar: --
gravies: 476.000001000.00000
hard candy: 0.010000.01000
imitation dairy: --
instant coffee / tea: 224.00000300.00000
jams / jellies: 373.00000500.00000
meat products: --
milk products: 700.000001000.00000
nut products: --
other grains: --
poultry: --
processed fruits: 37.0000050.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 249.00000356.00000
soups: --
sugar substitutes: 746.000001000.00000
sweet sauces: 746.000001000.00000

Safety references

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):140-10-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :444539
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(E)-3-phenylprop-2-enoic acid
Chemidplus:0000140103
RTECS:GD7850000 for cas# 140-10-3