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

Molecular Formula	C8H8O2
Molecular Weight	136.1479
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6857245	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis of cholesterol-conjugated magnetic nanoparticles for purification of human paraoxonase 1.	2010-10	19902382
A comparison of the in vitro biotransformation of (-)-epicatechin and procyanidin B2 by human faecal microbiota.	2010-06	19943260
Monitoring bioreactors using principal component analysis: production of penicillin G acylase as a case study.	2010-06	19727832
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.	2010-02-12	20018182
In vivo administration of BL-3050: highly stable engineered PON1-HDL complexes.	2009-11-17	19922610
Dramatic differences in organophosphorus hydrolase activity between human and chimeric recombinant mammalian paraoxonase-1 enzymes.	2009-11-03	19764813
High prevalence of low serum paraoxonase-1 in subjects with coronary artery disease.	2009-11	19902017
Developmental changes in PON1 enzyme activity in young children and effects of PON1 polymorphisms.	2009-10	20019917
Islet endothelial activation and oxidative stress gene expression is reduced by IL-1Ra treatment in the type 2 diabetic GK rat.	2009-09-09	19742300
Effect of loading rate and HRT on the removal of cephalosporin and their intermediates during the operation of a membrane bioreactor treating pharmaceutical wastewater.	2009-09	19886426
Thermostable lipases from the extreme thermophilic anaerobic bacteria Thermoanaerobacter thermohydrosulfuricus SOL1 and Caldanaerobacter subterraneus subsp. tengcongensis.	2009-09	19579003
Racial differences in paraoxonase-1 (PON1): a factor in the health of southerners?	2009-08	19672401
Chemical and enzymatic stability of amino acid prodrugs containing methoxy, ethoxy and propylene glycol linkers.	2009-07-02	19566080
Synthesis and evaluation of in vitro antiviral activity of novel phenoxy acetic acid derivatives.	2009-06	18951282
Molecular characterization of a fungal gene paralogue of the penicillin penDE gene of Penicillium chrysogenum.	2009-05-26	19470155
Total synthesis of psoralidin, an anticancer natural product.	2009-04-03	19254011
Modulation of butyrate transport in Caco-2 cells.	2009-04	19023563
Paraoxonase 1 activity in different types of multiple sclerosis.	2009-03	18845659
Determinants of variation in human serum paraoxonase activity.	2009-02	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.	2009-02	18505467
Discovery and implementation of transcriptional biomarkers of synthetic LXR agonists in peripheral blood cells.	2008-10-16	18925943
Molecular basis of halorespiration control by CprK, a CRP-FNR type transcriptional regulator.	2008-10	18717788
Inhibitory effect of some acetyl esters and acetamides on glycation of the histone H1.	2008-09-25	18810996
Localization and characterization of the novel protein encoded by C20orf3.	2008-09-15	18513186
Effect of 7Li radiation on endogenous hormonal level on developing cotton fiber.	2008-09	18949898
Synthesis and biological effect of halogen substituted phenyl acetic acid derivatives of progesterone as potent progesterone receptor antagonists.	2008-09	18625316
Predicting reactivities of organic molecules. Theoretical and experimental studies on the aminolysis of phenyl acetates.	2008-07-24	18578479
Topical ocular delivery of NSAIDs.	2008-06	18437583
Simple procedures for purification and stabilization of human serum paraoxonase-1.	2008-04-24	17928061
Efficacy and tolerability of lumiracoxib, a highly selective cyclo-oxygenase-2 (COX2) inhibitor, in the management of pain and osteoarthritis.	2008-04	18728796
A diazonium ion cascade from the nitrosation of tolazoline, an imidazoline-containing drug.	2008-02	18247523
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
Bioreversible derivatives of phenol. 2. Reactivity of carbonate esters with fatty acid-like structures towards hydrolysis in aqueous solutions.	2007-10-30	17978765
The distribution of esterases in the skin of the minipig.	2007-09-10	17719730
Functional characterization of the penicillin biosynthetic gene cluster of Penicillium chrysogenum Wisconsin54-1255.	2007-09	17548217
Nanostructured biosensor for measuring neuropathy target esterase activity.	2007-07-15	17555296
Reduced paraoxonase1 activity is a risk for atherosclerosis in patients with systemic lupus erythematosus.	2007-06	17893973
Further modification on phenyl acetic acid based quinolines as liver X receptor modulators.	2007-05-15	17391964
High yield recombinant penicillin G amidase production and export into the growth medium using Bacillus megaterium.	2006-11-28	17132166
Oxidative photo-decarboxylation in the presence of mesoporous silicas.	2006-11	17077555
Synthesis and properties of novel unsymmetrical donor molecules containing p-acetoxy- or p-hydroxyphenyl units.	2006-10-21	17971754
Discovery of phenyl acetic acid substituted quinolines as novel liver X receptor agonists for the treatment of atherosclerosis.	2006-10-19	17034119
Inhibitory mode of 2-acetoxyphenyl alkyl sulfides against COX-1 and COX-2: QSAR analyses.	2006-10-15	16908140
Synthesis and evaluation of phenoxy acetic acid derivatives as [corrected] anti-mycobacterial agents.	2006-09-01	16784842
Polymer supported vanadium and molybdenum complexes as potential catalysts for the oxidation and oxidative bromination of organic substrates.	2006-08-07	16855757
Lead exposure is associated with decreased serum paraoxonase 1 (PON1) activity and genotypes.	2006-08	16882531
Activity of paraoxonase 1 (PON1) and its relationship to markers of lipoprotein oxidation in healthy Slovaks.	2006	17106515
Serum arylesterase and paraoxonase activity in patients with chronic hepatitis.	2005-12-14	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.	2005-07-21	16833969

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:45:31 GMT 2025` Edited by `admin` on `Mon Mar 31 17:45:31 GMT 2025`
Record UNII	355G9R500Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENYL ACETATE

Systematic Name

English

FEMA NO. 3958

Preferred 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

ACETOXYBENZENE

Systematic Name

English

(ACETYLOXY)BENZENE

Systematic Name

English

PHENOL ACETATE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

77993