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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

2023
455
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 5.21 mM [IC50]
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Phytotoxicity of vulpia residues: III. Biological activity of identified allelochemicals from Vulpia myuros.
2001 Feb
Phenylpropanoid interconversion in Anigozanthos preissii observed by high-performance liquid chromatography-nuclear magnetic resonance spectroscopy.
2001 Jan-Feb
Metabolism of phenylpropionic acid in enteropathogenic Escherichia coli belonging to serogroup O111 and its application for diagnosis.
2001 Oct 16
Fermentation of cottonseed and other feedstuffs in cattle rumen fluid.
2002 Apr 10
The loading and initial elongation modules of rifamycin synthetase collaborate to produce mixed aryl ketide products.
2002 Apr 23
Synthesis of cyclic prodrugs of Aggrastat and its analogue with a modified phenylpropionic acid linker.
2002 Feb 21
Design, synthesis and evaluation of substituted phenylpropanoic acid derivatives as peroxisome proliferator-activated receptor (PPAR) activators: novel human PPARalpha-selective activators.
2002 Jan 7
Dynamic changes in cell wall polysaccharides during wheat seedling development.
2002 Jul
Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630.
2002 May
[Effect of nandrolone phenylpropionate on hepatic albumin mRNA and granulational alpha 1(I) procollagen mRNA in burned rats].
2004 Jan
[Effects of nandrolone phenylpropionate on fibroblasts after injury in rats].
2004 Jul
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
2004 Jul 2
Structure-property correlation of a new family of organogelators based on organic salts and their selective gelation of oil from oil/water mixtures.
2004 Oct 25
The pig caecum model: a suitable tool to study the intestinal metabolism of flavonoids.
2004 Sep
Catalytic mechanism of C-C hydrolase MhpC from Escherichia coli: kinetic analysis of His263 and Ser110 site-directed mutants.
2005 Feb 11
Sub-Tg relaxations due to dipolar solutes in nonpolar glass-forming solvents.
2005 Jan 1
Dakin-West synthesis of beta-aryl ketones.
2006 Aug 18
[Chromatographic mass spectrometric determination of low-molecular-weight aromatic compounds of microbial origin in the serum from patients with sepsis].
2006 Feb
Biosynthesis of plant-specific stilbene polyketides in metabolically engineered Escherichia coli.
2006 Mar 21
Expression, purification and crystallization of 2-oxo-hept-4-ene-1,7-dioate hydratase (HpcG) from Escherichia coli C.
2006 Oct 1
Highly efficient preparation of lipophilic hydroxycinnamates by solvent-free lipase-catalyzed transesterification.
2006 Sep 20
Biological activity of phenylpropionic acid isolated from a terrestrial Streptomycetes.
2007
Stable, high-efficiency ionic-liquid-based mesoscopic dye-sensitized solar cells.
2007 Dec
Treatment of vegetable sauces with enterocin AS-48 alone or in combination with phenolic compounds to inhibit proliferation of Staphylococcus aureus.
2007 Feb
[GC-MS analysis of volatile constituents from five different kinds of Chinese eaglewood].
2007 May
Treatment of landfill leachate by electrochemical oxidation and anaerobic process.
2007 May
Efficacy of enterocin AS-48 against bacilli in ready-to-eat vegetable soups and purees.
2007 Oct
Effects of aromatic amino acids, phenylacetate and phenylpropionate on fermentation of xylan by the rumen anaerobic fungi, Neocallimastix frontalis and Piromyces communis.
2007 Oct
Flavanol monomer-induced changes to the human faecal microflora.
2008 Apr
Hair analysis of anabolic steroids in connection with doping control-results from horse samples.
2008 Jul
Azide-selective sensor based on tripodal iron complex for direct azide determination in aqueous samples.
2008 Jul
Application of temperature-controlled micro planar chromatography for separation and quantification of testosterone and its derivatives.
2008 Jul
Strain improvement of recombinant Escherichia coli for efficient production of plant flavonoids.
2008 Mar-Apr
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 May 1
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 Fri Dec 15 19:05:58 GMT 2023
Edited
by admin
on Fri Dec 15 19:05:58 GMT 2023
Record UNII
5Q445IN5CU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3-PHENYL PROPIONIC ACID
Systematic 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  
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 Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
Code System Code Type Description
FDA UNII
5Q445IN5CU
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
CAS
501-52-0
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
NSC
9272
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
CHEBI
28631
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
PUBCHEM
107
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
DAILYMED
5Q445IN5CU
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID2047064
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
MERCK INDEX
m6092
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY Merck Index
JECFA MONOGRAPH
179
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
WIKIPEDIA
Hydrocinnamic acid
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-924-5
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
DRUG BANK
DB02024
Created by admin on Fri Dec 15 19:05:58 GMT 2023 , Edited by admin on Fri Dec 15 19:05:58 GMT 2023
PRIMARY
NIH
NCATS
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