Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H10O2 |
| Molecular Weight | 150.1745 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC1=CC=CC=C1
InChI
InChIKey=XMIIGOLPHOKFCH-UHFFFAOYSA-N
InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)
3-Phenylpropionic acid (hydrocinnamic acid, HA) is an end-product of the bacterial degradation of unabsorbed phenylalanine in the intestinal lumen. HA is used in ice cream, drinks, and
candy manufacture field as a flavoring agent. In recent
years, HA is widely used in the pharmaceutical industry. Hydrocinnamic Acid inhibits the currents of WT and SQT3 syndrome-related mutants of Kir2.1 channel.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hair analysis of anabolic steroids in connection with doping control-results from horse samples. | 2008-07 |
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| Azide-selective sensor based on tripodal iron complex for direct azide determination in aqueous samples. | 2008-07 |
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| Application of temperature-controlled micro planar chromatography for separation and quantification of testosterone and its derivatives. | 2008-07 |
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| Effects of modifications of the linker in a series of phenylpropanoic acid derivatives: Synthesis, evaluation as PPARalpha/gamma dual agonists, and X-ray crystallographic studies. | 2008-05-01 |
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| Heterometallic integer-spin analogues of S = 9/2 Mn4 cubane single-molecule magnets. | 2008-04-21 |
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| Kinetic mechanism of phenylacetone monooxygenase from Thermobifida fusca. | 2008-04-01 |
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| Flavanol monomer-induced changes to the human faecal microflora. | 2008-04 |
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| Strain improvement of recombinant Escherichia coli for efficient production of plant flavonoids. | 2008-03-13 |
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| Green brazilian propolis action on macrophages and lymphoid organs of chronically stressed mice. | 2008-03 |
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| Potential chemosignals in the anogenital gland secretion of giant pandas, Ailuropoda melanoleuca, associated with sex and individual identity. | 2008-03 |
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| SAR-oriented discovery of peroxisome proliferator-activated receptor pan agonist with a 4-adamantylphenyl group as a hydrophobic tail. | 2008-02-01 |
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| Preconcentration, separation, and indirect detection of nonfluorescent analytes using fluorescent mobility markers. | 2008-01-01 |
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| Infrared imaging of sunflower and maize root anatomy. | 2007-12-26 |
|
| Removal of pharmaceuticals and personal care products (PPCPs) from urban wastewater in a pilot vertical flow constructed wetland and a sand filter. | 2007-12-01 |
|
| Stable, high-efficiency ionic-liquid-based mesoscopic dye-sensitized solar cells. | 2007-12 |
|
| Efficacy of enterocin AS-48 against bacilli in ready-to-eat vegetable soups and purees. | 2007-10 |
|
| Effects of aromatic amino acids, phenylacetate and phenylpropionate on fermentation of xylan by the rumen anaerobic fungi, Neocallimastix frontalis and Piromyces communis. | 2007-10 |
|
| Improved high-performance liquid chromatography-diode array detection method for the determination of phenolic compounds in leaves and peels from different apple varieties. | 2007-09 |
|
| Three phase liquid phase microextraction of phenylacetic acid and phenylpropionic acid from biological fluids. | 2007-08-15 |
|
| Phenylpropanoic acid derivatives bearing a benzothiazole ring as PPARdelta-selective agonists. | 2007-08-01 |
|
| Comparative study of charge division in substituted benzene cations. | 2007-06-14 |
|
| Weakening of salmonella with selected microbial metabolites of berry-derived phenolic compounds and organic acids. | 2007-05-16 |
|
| [GC-MS analysis of volatile constituents from five different kinds of Chinese eaglewood]. | 2007-05 |
|
| Treatment of landfill leachate by electrochemical oxidation and anaerobic process. | 2007-05 |
|
| 4-Phenylbutyrate restores the functionality of a misfolded mutant low-density lipoprotein receptor. | 2007-04 |
|
| Treatment of vegetable sauces with enterocin AS-48 alone or in combination with phenolic compounds to inhibit proliferation of Staphylococcus aureus. | 2007-02 |
|
| The disposition and metabolism of naveglitazar, a peroxisome proliferator-activated receptor alpha-gamma dual, gamma-dominant agonist in mice, rats, and monkeys. | 2007-01 |
|
| Biological activity of phenylpropionic acid isolated from a terrestrial Streptomycetes. | 2007 |
|
| High-performance functional ecopolymers based on flora and fauna. | 2007 |
|
| Early onset pauciarticular arthritis is the major risk factor for naproxen-induced pseudoporphyria in juvenile idiopathic arthritis. | 2007 |
|
| Effects of chromophore orientation and molecule conformation on surface-enhanced Raman scattering studied with alkanoic acids and colloidal silver nanoparticles. | 2006-12-21 |
|
| Expression of gentisate 1,2-dioxygenase (gdoA) genes involved in aromatic degradation in two haloarchaeal genera. | 2006-12 |
|
| [Toxicity reduction of synthetic municipal wastewater treated by anaerobic, anoxic or aerobic reactors]. | 2006-11 |
|
| Isolation and characterization of antifungal substances from Burkholderia sp. culture broth. | 2006-11 |
|
| Expression, purification and crystallization of 2-oxo-hept-4-ene-1,7-dioate hydratase (HpcG) from Escherichia coli C. | 2006-10-01 |
|
| Highly efficient preparation of lipophilic hydroxycinnamates by solvent-free lipase-catalyzed transesterification. | 2006-09-20 |
|
| Dakin-West synthesis of beta-aryl ketones. | 2006-08-18 |
|
| HCl-induced inflammatory mediators in cat esophageal mucosa and inflammatory mediators in esophageal circular muscle in an in vitro model of esophagitis. | 2006-06 |
|
| Slow-binding human serine racemase inhibitors from high-throughput screening of combinatorial libraries. | 2006-04-20 |
|
| Pelotomaculum terephthalicum sp. nov. and Pelotomaculum isophthalicum sp. nov.: two anaerobic bacteria that degrade phthalate isomers in syntrophic association with hydrogenotrophic methanogens. | 2006-04 |
|
| Biosynthesis of plant-specific stilbene polyketides in metabolically engineered Escherichia coli. | 2006-03-21 |
|
| [Chromatographic mass spectrometric determination of low-molecular-weight aromatic compounds of microbial origin in the serum from patients with sepsis]. | 2006-02 |
|
| Design and synthesis of substituted phenylpropanoic acid derivatives as human peroxisome proliferator-activated receptor alpha/delta dual agonists. | 2006-02 |
|
| Chemical constituents of the aquatic plant Schoenoplectus lacustris: evaluation of phytotoxic effects on the green alga Selenastrum capricornutum. | 2006-01 |
|
| Use of the pig caecum model to mimic the human intestinal metabolism of hispidulin and related compounds. | 2006-01 |
|
| Asymmetric conjugate reduction of alpha,beta-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts. | 2005-12-16 |
|
| Induction and quantification of phenylacyl-CoA ligase enzyme activities in Pseudomonas putida CA-3 grown on aromatic carboxylic acids. | 2005-10-15 |
|
| [High performance liquid chromatographic determination of cinnamic acid in rabbit plasma and application in study of pharmacokinetics]. | 2005-05 |
|
| [Expression of androgen receptor on fibroblast and hepatocyte of rats after deep second-degree burn caused by scalding]. | 2005-05 |
|
| Production of aromatic compounds during methanogenic degradation of straw in rice field soil. | 2005-03-01 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: A 20 mg bolus with infusion of 1 mg/min of phenylpropionic acid decreased blood glucose levels of normal [110 +/- 12 to 66 +/- 11 mg/dL, N = 7, P < 0.05 (unpaired Student's t-test vs control)] and streptozocin diabetic rats [295 +/- 14 to 225 +/- 12 mg/dL, N = 7, P < 0.01 (paired t-test vs basal)]. https://www.ncbi.nlm.nih.gov/pubmed/8960065
Intraperitoneal injection of hydrocinnamic (beta-phenylpropionic) acid inhibited gluconeogenesis from 14C-1-alanine, 14C-1-oleate oxidation, and intensified 14C-1-glucose oxidation in normal and diabetic rats.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Curator's Comment: The Kir2.1 currents were recorded after 24-h
transfection of Kir2.1 DNA plasmid to HEK293T cells.
Kir2.1 showed very strong inwardly rectifying properties.
3-Phenylpropionic acid (hydrocinnamic acid, HA) can inhibit the currents of Kir2.1 channel in both excised inside-out and whole-cell patch with the IC50 of 5.21 ± 1.02 and 10.08 ± 0.46 mM, respectively. 20 mM HA completely
abolished the currents.
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JECFA EVALUATION |
3-PHENYLPROPIONIC ACID
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CFR |
21 CFR 172.515
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5Q445IN5CU
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501-52-0
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9272
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28631
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107
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5Q445IN5CU
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DTXSID2047064
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m6092
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179
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Hydrocinnamic acid
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207-924-5
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DB02024
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SUBSTANCE RECORD
