U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C8H8O3
Molecular Weight 152.1473
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENOXYACETIC ACID

SMILES

OC(=O)COC1=CC=CC=C1

InChI

InChIKey=LCPDWSOZIOUXRV-UHFFFAOYSA-N
InChI=1S/C8H8O3/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.hmdb.ca/metabolites/HMDB31609 and http://www.ncbi.nlm.nih.gov/pubmed/9454687

Phenoxyacetic acid is found in cocoa and cocoa products. Phenoxyacetic acid is a flavouring ingredient. Phenoxyacetic acid is on the FDA list of approved food additives (PART 172 - FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION; Subpart F--Flavoring Agents and Related Substances Sec. 172.515 Synthetic flavoring substances and adjuvants.). Research has shown that Phenoxyacetic acid induced hematopoietic cell proliferation, providing potential for oral therapeutics which stimulate proliferation of hematopoietic cells of multiple lineages, as well as inducing fetal globin, important for therapy of hemoglobinopathies.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Erythroid progenitor proliferation
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Immuno-arrays for multianalyte analysis of chlorotriazines.
2005 Jan 30
Analytical methods of biological monitoring for exposure to pesticides: recent update.
2007 Apr
Uptake of pesticides from water by curly waterweed Lagarosiphon major and lesser duckweed Lemna minor.
2007 Aug
2-Cycloalkyl phenoxyacetic acid CRTh2 receptor antagonists.
2007 Aug 1
Tetra-kis(μ-phenoxy-acetato-κO:O')bis-[(1,10-phenanthroline-κN,N')manganese(II)] methanol hemisolvate.
2007 Dec 12
Poly[[diaqua-nickel(II)]-μ(2)-4,4'-bipyridine-κN:N'-μ-p-phenyl-enedioxy-diacetato-κO:O'].
2007 Dec 6
Synthesis, characterization and antibacterial activity of azomethine derivatives derived from 2-formylphenoxyacetic acid.
2007 Feb 22
The role of laterally transferred genes in adaptive evolution.
2007 Feb 8
Agricultural exposures and gastric cancer risk in Hispanic farm workers in California.
2007 Jun
Substituent and solvent effects on electronic spectra of some substituted phenoxyacetic acids.
2007 Jun
Superheated water extraction and phase transfer methylation of phenoxy acid herbicides from solid matrices.
2007 Jun 8
Synthesis, biological evaluation, and molecular modeling investigation of chiral phenoxyacetic acid analogues with PPARalpha and PPARgamma agonist activity.
2007 May
Retention behavior of phenoxyacetic herbicides on a molecularly imprinted polymer with phenoxyacetic acid as a dummy template molecule.
2007 Sep 15
PPAR-delta in Vascular Pathophysiology.
2008
Structural Development Studies of Subtype-Selective Ligands for Peroxisome Proliferator-Activated Receptors (PPARs) Based on the 3,4-Disubstituted Phenylpropanoic Acid Scaffold as a Versatile Template.
2008
Analysis of phenoxyacetic acid herbicides as biomarkers in human urine using liquid chromatography/triple quadrupole mass spectrometry.
2008
Ultra-pressure liquid chromatography-electrospray tandem mass spectrometry for multiresidue determination of pesticides in water.
2008 Aug 22
Variation of MCPA, metribuzine, methyltriazine-amine and glyphosate degradation, sorption, mineralization and leaching in different soil horizons.
2008 Dec
Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives.
2008 Feb
Synthesis and characterization of molecularly imprinted polymers for phenoxyacetic acids.
2008 Jan
FT-IR, FT-Raman spectra and quantum chemical calculations of some chloro substituted phenoxy acetic acids.
2008 Jul
Direct analysis of tfdA gene expression by indigenous bacteria in phenoxy acid amended agricultural soil.
2008 Jun
Uptake of 4-chloro-2-methylphenoxyacetic acid (MCPA) from the apical membrane of Caco-2 cells by the monocarboxylic acid transporter.
2008 Mar 15
Polydopamine-based permanent coating capillary electrochromatography for auxin determination.
2008 Nov 28
Development of relatively selective, chemically and mechanically robust solid-phase microextraction fibers based on methacrylic acid-trimethylolpropanetrimethacrylate co-polymers.
2008 Oct 24
Spatial variation in 2-methyl-4-chlorophenoxyacetic acid mineralization and sorption in a sandy soil at field level.
2008 Sep-Oct
PPARδ activity in cardiovascular diseases: A potential pharmacological target.
2009
Automated potentiometric titrations in KCl/water-saturated octanol: method for quantifying factors influencing ion-pair partitioning.
2009 Apr 1
Causes and types of health effects during the use of crop protection chemicals: data from a survey of over 6,300 smallholder applicators in 24 different countries.
2009 Aug
Optimization of the dilute maleic acid pretreatment of wheat straw.
2009 Dec 21
Exploring and dissecting genome-wide gene expression responses of Penicillium chrysogenum to phenylacetic acid consumption and penicillinG production.
2009 Feb 10
Relative developmental toxicity of glycol ether alkoxy acid metabolites in the embryonic stem cell test as compared with the in vivo potency of their parent compounds.
2009 Jul
Allergic reaction induced by dermal and/or respiratory exposure to low-dose phenoxyacetic acid, organophosphorus, and carbamate pesticides.
2009 Jul 10
Hypersensitivity reactions to penicillins: studies in a group of patients with negative benzylpenicillin G skin test.
2009 Jun
Synthesis and evaluation of in vitro antiviral activity of novel phenoxy acetic acid derivatives.
2009 Jun
The University of Michigan Dioxin Exposure Study: predictors of human serum dioxin concentrations in Midland and Saginaw, Michigan.
2009 May
Uptake of phenoxyacetic acid derivatives into Caco-2 cells by the monocarboxylic acid transporters.
2009 Sep 10
Selection of sorbent for removing pesticides during water treatment.
2009 Sep 30
Discovery of carboranes as inducers of 20S proteasome activity.
2010 Aug 2
Novel approaches to inhibition of gastric acid secretion.
2010 Dec
The use of in vitro toxicity data and physiologically based kinetic modeling to predict dose-response curves for in vivo developmental toxicity of glycol ethers in rat and man.
2010 Dec
Prior exposure to organophosphorus and organochlorine pesticides increases the allergic potential of environmental chemical allergens in a local lymph node assay.
2010 Dec 15
Biomonitoring data for 2,4-dichlorophenoxyacetic acid in the United States and Canada: interpretation in a public health risk assessment context using Biomonitoring Equivalents.
2010 Feb
A new concept for reduction of diffuse contamination by simultaneous application of pesticide and pesticide-degrading microorganisms.
2010 Feb
Liquid chromatography with post-column reagent addition of ammonia in methanol coupled to negative ion electrospray ionization tandem mass spectrometry for determination of phenoxyacid herbicides and their degradation products in surface water.
2010 Feb 3
Synthesis of some new mono- and bis-polycyclic aromatic spiro and bis-nonspiro-beta-lactams.
2010 Jan 22
Impacts of stage-specific acute pesticide exposure on predicted population structure of the soft-shell clam, Mya arenaria.
2010 Jul 1
Decrease of intracellular pH as possible mechanism of embryotoxicity of glycol ether alkoxyacetic acid metabolites.
2010 Jun 1
A simple and sensitive HPLC method for quantification of the metabolin of meclofenoxate in human plasma.
2010 May-Jun
Comparative transcriptome profiling analyses during the lag phase uncover YAP1, PDR1, PDR3, RPN4, and HSF1 as key regulatory genes in genomic adaptation to the lignocellulose derived inhibitor HMF for Saccharomyces cerevisiae.
2010 Nov 24
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
1.0 mM phenoxyacetic acid increased cell proliferation 2 to 3-fold despite IL-3 depletion in human IL-3 dependent multi-lineage cell line (32D)
Name Type Language
PHENOXYACETIC ACID
FHFI   MI  
Systematic Name English
PHENOXYMETHYLPENICILLIN IMPURITY B [EP IMPURITY]
Common Name English
PHENOXYETHANOIC ACID
Systematic Name English
NSC-9810
Code English
FEMA NO. 2872
Code English
PHENOXYMETHYLPENICILLIN (BENZATHINE) TETRAHYDRATE IMPURITY B [EP IMPURITY]
Common Name English
PHENOXYACETIC ACID [FHFI]
Common Name English
PHENOXYACETIC ACID [MI]
Common Name English
O-PHENYLGLYCOLIC ACID
Systematic Name English
PHENYL ETHER GLYCOLIC ACID
Systematic Name English
PHENOXYMETHYLPENICILLIN POTASSIUM IMPURITY B [EP IMPURITY]
Common Name English
Classification Tree Code System Code
JECFA EVALUATION PHENOXYACETIC ACID
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
Code System Code Type Description
MESH
C415326
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
CONCEPT Industrial Aid
EPA CompTox
DTXSID9025873
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-556-7
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
CAS
122-59-8
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
NCI_THESAURUS
C84049
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
FDA UNII
YRC253429Q
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
PUBCHEM
19188
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
MERCK INDEX
m8636
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
Phenoxyacetic acid
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
CHEBI
8075
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
RXCUI
1426335
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY RxNorm
NSC
9810
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
CHEBI
38846
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
JECFA MONOGRAPH
959
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY
RXCUI
1426336
Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023
PRIMARY