PHENYL ACETATE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H8O2
Molecular Weight	136.1479
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)OC1=CC=CC=C1

InChI

InChIKey=IPBVNPXQWQGGJP-UHFFFAOYSA-N

InChI=1S/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3

HIDE SMILES / InChI

Description
Sources: http://www.chemicalbook.com/ChemicalProductProperty_EN_CB0300805.htm |https://www.ncbi.nlm.nih.gov/pubmed/23950599 | https://www.ncbi.nlm.nih.gov/pubmed/6857245 | https://www.ncbi.nlm.nih.gov/pubmed/12729627

Phenylacetate is the ester of a phenol and acetic acid. It is a metabolite of anticancer drug phenylbutyrate (PB), natural neurotransmitter phenylethylamine. Naturally, it is an odorant found in strawberries, passion fruit, and black tea. Phenylacetate level in urine was used as a marker for the diagnosis of some forms of unipolar major depressive disorders. Phenylacetate is used as a tool substrate to study esterase activity in the blood of patients in clinical studies of the effect of nutritional supplements on paraoxonase-1 levels.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serum paraoxonase/arylesterase 1 31 Target ID: CHEMBL3167 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12729627	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6857245	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Serum arylesterase and paraoxonase activity in patients with chronic hepatitis.	2005 Dec 14	16437641
Ab initio study of the substituent effects on the relative stability of the E and Z conformers of phenyl esters. Stereoelectronic effects on the reactivity of the carbonyl group.	2005 Jul 21	16833969
Activity of paraoxonase 1 (PON1) and its relationship to markers of lipoprotein oxidation in healthy Slovaks.	2006	17106515
Lead exposure is associated with decreased serum paraoxonase 1 (PON1) activity and genotypes.	2006 Aug	16882531
Polymer supported vanadium and molybdenum complexes as potential catalysts for the oxidation and oxidative bromination of organic substrates.	2006 Aug 7	16855757
Oxidative photo-decarboxylation in the presence of mesoporous silicas.	2006 Nov	17077555
High yield recombinant penicillin G amidase production and export into the growth medium using Bacillus megaterium.	2006 Nov 28	17132166
Inhibitory mode of 2-acetoxyphenyl alkyl sulfides against COX-1 and COX-2: QSAR analyses.	2006 Oct 15	16908140
Discovery of phenyl acetic acid substituted quinolines as novel liver X receptor agonists for the treatment of atherosclerosis.	2006 Oct 19	17034119
Synthesis and properties of novel unsymmetrical donor molecules containing p-acetoxy- or p-hydroxyphenyl units.	2006 Oct 21	17971754
Synthesis and evaluation of phenoxy acetic acid derivatives as [corrected] anti-mycobacterial agents.	2006 Sep 1	16784842
Nanostructured biosensor for measuring neuropathy target esterase activity.	2007 Jul 15	17555296
Reduced paraoxonase1 activity is a risk for atherosclerosis in patients with systemic lupus erythematosus.	2007 Jun	17893973
Further modification on phenyl acetic acid based quinolines as liver X receptor modulators.	2007 May 15	17391964
Bioreversible derivatives of phenol. 2. Reactivity of carbonate esters with fatty acid-like structures towards hydrolysis in aqueous solutions.	2007 Oct 30	17978765
Functional characterization of the penicillin biosynthetic gene cluster of Penicillium chrysogenum Wisconsin54-1255.	2007 Sep	17548217
The distribution of esterases in the skin of the minipig.	2007 Sep 10	17719730
Paraoxonases (PON1, PON2, PON3) analyses in vitro and in vivo in relation to cardiovascular diseases.	2008	19082953
Genetically-based olfactory signatures persist despite dietary variation.	2008	18974891
Efficacy and tolerability of lumiracoxib, a highly selective cyclo-oxygenase-2 (COX2) inhibitor, in the management of pain and osteoarthritis.	2008 Apr	18728796
Simple procedures for purification and stabilization of human serum paraoxonase-1.	2008 Apr 24	17928061
A diazonium ion cascade from the nitrosation of tolazoline, an imidazoline-containing drug.	2008 Feb	18247523
Predicting reactivities of organic molecules. Theoretical and experimental studies on the aminolysis of phenyl acetates.	2008 Jul 24	18578479
Inhibitory effect of some acetyl esters and acetamides on glycation of the histone H1.	2008 Jul-Aug	18810996
Topical ocular delivery of NSAIDs.	2008 Jun	18437583
Molecular basis of halorespiration control by CprK, a CRP-FNR type transcriptional regulator.	2008 Oct	18717788
Discovery and implementation of transcriptional biomarkers of synthetic LXR agonists in peripheral blood cells.	2008 Oct 16	18925943
Effect of 7Li radiation on endogenous hormonal level on developing cotton fiber.	2008 Sep	18949898
Synthesis and biological effect of halogen substituted phenyl acetic acid derivatives of progesterone as potent progesterone receptor antagonists.	2008 Sep	18625316
Localization and characterization of the novel protein encoded by C20orf3.	2008 Sep 15	18513186
Modulation of butyrate transport in Caco-2 cells.	2009 Apr	19023563
Total synthesis of psoralidin, an anticancer natural product.	2009 Apr 3	19254011
Racial differences in paraoxonase-1 (PON1): a factor in the health of southerners?	2009 Aug	19672401
Determinants of variation in human serum paraoxonase activity.	2009 Feb	18971955
High plasma C-reactive protein (CRP) is related to low paraoxonase-I (PON-I) activity independently of high leptin and low adiponectin in type 2 diabetes mellitus.	2009 Feb	18505467
Synthesis and evaluation of in vitro antiviral activity of novel phenoxy acetic acid derivatives.	2009 Jun	18951282
Paraoxonase 1 activity in different types of multiple sclerosis.	2009 Mar	18845659
Molecular characterization of a fungal gene paralogue of the penicillin penDE gene of Penicillium chrysogenum.	2009 May 26	19470155
High prevalence of low serum paraoxonase-1 in subjects with coronary artery disease.	2009 Nov	19902017
In vivo administration of BL-3050: highly stable engineered PON1-HDL complexes.	2009 Nov 17	19922610
Dramatic differences in organophosphorus hydrolase activity between human and chimeric recombinant mammalian paraoxonase-1 enzymes.	2009 Nov 3	19764813
Developmental changes in PON1 enzyme activity in young children and effects of PON1 polymorphisms.	2009 Oct	20019917
Effect of loading rate and HRT on the removal of cephalosporin and their intermediates during the operation of a membrane bioreactor treating pharmaceutical wastewater.	2009 Sep	19886426
Thermostable lipases from the extreme thermophilic anaerobic bacteria Thermoanaerobacter thermohydrosulfuricus SOL1 and Caldanaerobacter subterraneus subsp. tengcongensis.	2009 Sep	19579003
Islet endothelial activation and oxidative stress gene expression is reduced by IL-1Ra treatment in the type 2 diabetic GK rat.	2009 Sep 9	19742300
Chemical and enzymatic stability of amino acid prodrugs containing methoxy, ethoxy and propylene glycol linkers.	2009 Sep-Oct	19566080
3-(4-(Benzo[d]thiazol-2-yl)-1-phenyl-1H-pyrazol-3-yl) phenyl acetate induced Hep G2 cell apoptosis through a ROS-mediated pathway.	2010 Feb 12	20018182
A comparison of the in vitro biotransformation of (-)-epicatechin and procyanidin B2 by human faecal microbiota.	2010 Jun	19943260
Monitoring bioreactors using principal component analysis: production of penicillin G acylase as a case study.	2010 Jun	19727832
Synthesis of cholesterol-conjugated magnetic nanoparticles for purification of human paraoxonase 1.	2010 Oct	19902382

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Arylesterase activity was measured as the rate of hydrolysis of phenylacetate into phenol. This process can be detected spectrophotometrically. Serum samples were prepared in sample buffer consisting of 20 mM Tris and 0.9 mM CaCl2 (pH 8.0) in a 40-fold dilution. Five ul of diluted serum was then added to 200 ul of freshly made substrate buffer containing 1 mM phenylacetate, 20 mM Tris, and 0.9 mM CaCl2. The reaction was monitored on a microtiter plate at 260 nm in a Fluostar microplate reader at 37°C. The nonenzymatic hydrolysis of phenylacetate, based on the hydrolysis rate in the absence of serum, was subtracted from the total rate of hydrolysis.

Name

Type

Language

PHENYL ACETATE

Systematic Name

English

PHENYL ACETATE [HSDB]

Common Name

English

ACETIC ACID, PHENYL ESTER

Common Name

English

PHENYLACETATE

Systematic Name

English

PHENYL ACETATE [FHFI]

Common Name

English

PHENYL ACETATE [MI]

Common Name

English

NSC-27795

Code

English

FEMA NO. 3958

Code

English

ACETOXYBENZENE

Systematic Name

English

(ACETYLOXY)BENZENE

Systematic Name

English

PHENOL ACETATE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

77993