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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
Structure of 3-PHENYL PROPIONIC ACID

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)

HIDE SMILES / InChI
Molecular Formula C9H10O2
Molecular Weight 150.1745
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 5.21 mM [IC50]
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Hair analysis of anabolic steroids in connection with doping control-results from horse samples.
2008-07
Azide-selective sensor based on tripodal iron complex for direct azide determination in aqueous samples.
2008-07
Application of temperature-controlled micro planar chromatography for separation and quantification of testosterone and its derivatives.
2008-07
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
Heterometallic integer-spin analogues of S = 9/2 Mn4 cubane single-molecule magnets.
2008-04-21
Kinetic mechanism of phenylacetone monooxygenase from Thermobifida fusca.
2008-04-01
Flavanol monomer-induced changes to the human faecal microflora.
2008-04
Strain improvement of recombinant Escherichia coli for efficient production of plant flavonoids.
2008-03-13
Green brazilian propolis action on macrophages and lymphoid organs of chronically stressed mice.
2008-03
Potential chemosignals in the anogenital gland secretion of giant pandas, Ailuropoda melanoleuca, associated with sex and individual identity.
2008-03
SAR-oriented discovery of peroxisome proliferator-activated receptor pan agonist with a 4-adamantylphenyl group as a hydrophobic tail.
2008-02-01
Preconcentration, separation, and indirect detection of nonfluorescent analytes using fluorescent mobility markers.
2008-01-01
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
Patents

Patents

04775692
11
05670299
4
05741800
1
06060462
1
07208493
7
07777077
1
07989624
2
08394846
1
JP2001226333A
2
JP2002371030A
2
JP2007001912A
2
JP2008524166A
1
JP2009544443A
13
JP4154339B2
1
JPH02113836A
3
JPH11315064A
2
JPS62248494A
1

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:32:31 GMT 2025
Edited
by admin
on Mon Mar 31 19:32:31 GMT 2025
Record UNII
5Q445IN5CU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3-PHENYL PROPIONIC ACID
Systematic Name English
3-PHENYLPROPIONIC ACID
FHFI  
Preferred Name English
HYDROCINNAMIC ACID
MI  
Systematic Name English
HYDROCINNAMIC ACID [MI]
Common Name English
.BETA.-PHENYLPROPANOIC ACID
Systematic Name English
NSC-9272
Code English
BENZENEPROPANOIC ACID
Systematic Name English
3-PHENYLPROPIONIC ACID [FHFI]
Common Name English
FEMA NO. 2889
Code English
DIHYDROCINNAMIC ACID
Systematic Name English
Classification Tree Code System Code
JECFA EVALUATION 3-PHENYLPROPIONIC ACID
Created by admin on Mon Mar 31 19:32:31 GMT 2025 , Edited by admin on Mon Mar 31 19:32:31 GMT 2025
CFR 21 CFR 172.515
Created by admin on Mon Mar 31 19:32:31 GMT 2025 , Edited by admin on Mon Mar 31 19:32:31 GMT 2025
Code System Code Type Description
FDA UNII
5Q445IN5CU
Created by admin on Mon Mar 31 19:32:31 GMT 2025 , Edited by admin on Mon Mar 31 19:32:31 GMT 2025
PRIMARY
CAS
501-52-0
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PRIMARY
NSC
9272
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PRIMARY
CHEBI
28631
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PRIMARY
PUBCHEM
107
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PRIMARY
DAILYMED
5Q445IN5CU
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PRIMARY
EPA CompTox
DTXSID2047064
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PRIMARY
MERCK INDEX
m6092
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PRIMARY Merck Index
JECFA MONOGRAPH
179
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PRIMARY
WIKIPEDIA
Hydrocinnamic acid
Created by admin on Mon Mar 31 19:32:31 GMT 2025 , Edited by admin on Mon Mar 31 19:32:31 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-924-5
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PRIMARY
DRUG BANK
DB02024
Created by admin on Mon Mar 31 19:32:31 GMT 2025 , Edited by admin on Mon Mar 31 19:32:31 GMT 2025
PRIMARY
NIH
NCATS
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