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
Comparison of the gravimetric, phenol red, and 14C-PEG-3350 methods to determine water absorption in the rat single-pass intestinal perfusion model.	2001	11741276
An exploratory analysis of the effect of pesticide exposure on the risk of spontaneous abortion in an Ontario farm population.	2001 Aug	11564623
High-density lipoprotein composition and paraoxonase activity in Type I diabetes.	2001 Dec	11724654
Suppression of depleted uranium-induced neoplastic transformation of human cells by the phenyl fatty acid, phenyl acetate: chemoprevention by targeting the p21RAS protein pathway.	2001 Jan	11121229
Olfactory discrimination ability for aromatic odorants as a function of oxygen moiety.	2002 Jan	11751464
Heteropoly acid as a novel efficient catalyst for Fries rearrangement.	2002 Jun 7	12109070
The ratio of serum paraoxonase/arylesterase activity using an improved assay for arylesterase activity to discriminate PON1(R192) from PON1(Q192).	2003	15037822
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.	2004 Dec	15375178
Thermodynamically controlled synthesis of amide bonds catalyzed by highly organic solvent-resistant penicillin acylase derivatives.	2004 Jan-Feb	14763832
Enantioselective synthesis of phenylacetamides in the presence of high organic cosolvent concentrations catalyzed by stabilized penicillin G acylase. Effect of the acyl donor.	2004 May-Jun	15176909
Acetoclastic and hydrogenotrophic methane production and methanogenic populations in an acidic West-Siberian peat bog.	2004 Nov	15479249
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
High yield recombinant penicillin G amidase production and export into the growth medium using Bacillus megaterium.	2006 Nov 28	17132166
Synthesis and evaluation of phenoxy acetic acid derivatives as [corrected] anti-mycobacterial agents.	2006 Sep 1	16784842
Topical ocular delivery of NSAIDs.	2008 Jun	18437583
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
Total synthesis of psoralidin, an anticancer natural product.	2009 Apr 3	19254011
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
Paraoxonase 1 activity in different types of multiple sclerosis.	2009 Mar	18845659
High prevalence of low serum paraoxonase-1 in subjects with coronary artery disease.	2009 Nov	19902017
Dramatic differences in organophosphorus hydrolase activity between human and chimeric recombinant mammalian paraoxonase-1 enzymes.	2009 Nov 3	19764813
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
Chemical and enzymatic stability of amino acid prodrugs containing methoxy, ethoxy and propylene glycol linkers.	2009 Sep-Oct	19566080
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