ChemFOnt: Showing chemical card for Phenyl acetate (CFc000021604)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:13:28 UTC

Chemfont ID

CFc000021604

Molecule Identification

Common Name

Phenyl acetate

Definition

Phenyl acetate, also known as acetylphenol, is an aromatic fatty acid metabolite of phenylalanine with potential antineoplastic activity. Naturally occurring in mammals, phenylacetate induces differentiation, growth inhibition, and apoptosis in tumor cells. Its mechanisms of action include decreased protein prenylation, activation of the peroxisome proliferation-activated receptors, inhibition of DNA methylation, and depletion of glutamine. Phenyl acetate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Phenyl acetate has a phenolic-like taste.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acetic acid,phenyl ester	ChEBI
Acetylphenol	ChEBI
Phenol acetate	ChEBI
Acetate,phenyl ester	Generator
Phenol acetic acid	Generator
Phenyl acetic acid	Generator
Acetates	HMDB
Acetic acid phenyl ester	HMDB
Acetic acid, phenyl ester	HMDB
Acetoxybenzene	HMDB
Acetyl phenol	HMDB
FEMA 3958	HMDB
Fenylester kyseliny octove	HMDB
Phenyl ester OF acetic acid	HMDB

Chemical Formula

C₈H₈O₂

Average Molecular Weight

136.1479

Monoisotopic Molecular Weight

136.0524295

IUPAC Name

phenyl acetate

Traditional Name

phenyl acetate

CAS Registry Number

122-79-2

SMILES

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

InChI Identifier

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

InChI Key

IPBVNPXQWQGGJP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Monocyclic benzene moiety
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

acetate ester (CHEBI:8082 )

Functional Ontology

Physiological effect

Organoleptic effect

Odor

Phenolic

Feces (PMID: 27622378)

Cellular substructure

Extracellular (HMDB: HMDB0040733)
Cytoplasm (HMDB: HMDB0040733)

Source

Exogenous

Exogenous (HMDB: HMDB0040733)

Food

Food (HMDB: HMDB0040733)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040733)

Biological role

Nutrient (HMDB: HMDB0040733)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.19 g/L	ALOGPS
logP	1.59	ALOGPS
logP	1.58	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.19 m³·mol⁻¹	ChemAxon
Polarizability	14.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon