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

PubMed

Title	Date	PubMed
Macrophages are essential for lymphocyte infiltration in formyl peptide-induced cholangitis in rat liver.	1999 Jun	10395046
Hydrolysis of platelet-activating factor by human serum paraoxonase.	2001 Feb 15	11171072
Aspirin. An ab initio quantum-mechanical study of conformational preferences and of neighboring group interactions.	2001 Feb 9	11430095
Tyrosine and phenylalanine catabolism by Lactobacillus cheese flavor adjuncts.	2001 May	11384026
Species- and substrate-specific stimulation of human plasma paraoxonase 1 (PON1) activity by high chloride concentration.	2002	12545199
Olfactory discrimination ability for aromatic odorants as a function of oxygen moiety.	2002 Jan	11751464
Monitoring of enzymatic hydrolysis of penicillin G by pyrolysis-negative ion mass spectrometry.	2002 Jul 1	12062658
[The effects of paraoxonase-1 and oxidized low density lipoprotein on nephropathy in type-2 diabetes mellitus].	2002 Mar	11940319
Fast, easy, and efficient method for the purification of phenolic isomers using a selective solid-phase scavenging process.	2002 Nov-Dec	12425609
The ratio of serum paraoxonase/arylesterase activity using an improved assay for arylesterase activity to discriminate PON1(R192) from PON1(Q192).	2003	15037822
Europium ion catalyzed methanolysis of esters at neutral pH and ambient temperature. catalytic Involvement of Eu3+(CH3O-)(CH3OH)x.	2003 Jan 13	12513099
Observation of an arsenic adduct in an acetyl esterase crystal structure.	2003 Jan 17	12421810
Environmental fate and bioavailability of Agent Orange and its associated dioxin during the Vietnam War.	2004	15603524
Purification, substrate specificity, and N-terminal amino acid sequence analysis of a beta-lactamase-free penicillin amidase from Alcaligenes sp.	2004 Aug	15257420
[Decrease of paraoxonase activity in the first day after abdominal operations in women].	2004 Jul	15517772
A new class of acyclic 2-alkyl-1,1,2-triaryl (Z)-olefins as selective cyclooxygenase-2 inhibitors.	2004 Nov 18	15537365
Isolation of three new naturally occurring compounds from the culture of Micromonospora sp. P1068.	2005 Oct	16076633
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
High yield recombinant penicillin G amidase production and export into the growth medium using Bacillus megaterium.	2006 Nov 28	17132166
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
The distribution of esterases in the skin of the minipig.	2007 Sep 10	17719730
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
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
Modulation of butyrate transport in Caco-2 cells.	2009 Apr	19023563
Determinants of variation in human serum paraoxonase activity.	2009 Feb	18971955
Synthesis and evaluation of in vitro antiviral activity of novel phenoxy acetic acid derivatives.	2009 Jun	18951282
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
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
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
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:04:28 GMT 2023` Edited by `admin` on `Fri Dec 15 15:04:28 GMT 2023`
Record UNII	355G9R500Y
Record Status	`Validated (UNII)`
Record Version

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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