ContaminantDB: Ethenyl acetate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:58:33 UTC

Update Date

2016-11-09 01:08:52 UTC

Accession Number

CHEM002499

Identification

Common Name

Ethenyl acetate

Class

Small Molecule

Description

Polyvinyl acetate is used as a food additive [EAFUS] (EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]). Ethenyl acetate belongs to the family of Carboxylic Acid Esters. These are carboxylic acid derivatives in which the carbo atom from the carbonyl group is atached to an alkyl or oaryl moiety through an oxygen atom (forming an ester group).

Contaminant Sources

Clean Air Act Chemicals
EAFUS Chemicals
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 2B
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
Tobacco Smoke Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Cigarette Toxin
Ester
Food Toxin
Household Toxin
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Lachrymator
Metabolite
Organic Compound
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Acetoxyethylene	ChEBI
Acetic acid ethenyl ester	ChEBI
Acetic acid vinyl ester	ChEBI
Acetoxyethene	ChEBI
Essigsaeurevinylester	ChEBI
Ethenyl ethanoate	ChEBI
Vinyl ethanoate	ChEBI
Vinylacetat	ChEBI
Vinylazetat	ChEBI
Acetate ethenyl ester	Generator
Acetate vinyl ester	Generator
Ethenyl ethanoic acid	Generator
Vinyl ethanoic acid	Generator
Ethenyl acetic acid	Generator
CH3CO2CH=ch2	HMDB
Ethenyl acetate, 9ci	HMDB
Everflex 81l	HMDB
Unocal 76 res 6206	HMDB
Unocal 76 res S-55	HMDB
VAC	HMDB
Vinile	HMDB
Vinnapas a 50	HMDB
Vinyl acetate	HMDB
Vinyl ester OF acetic acid	HMDB
Vinyle	HMDB
Vinyl acetic acid	Generator
Polyvinyl acetic acid	Generator

Chemical Formula

C₄H₆O₂

Average Molecular Mass

86.089 g/mol

Monoisotopic Mass

86.037 g/mol

CAS Registry Number

108-05-4

IUPAC Name

ethenyl acetate

Traditional Name

vinyl acetate

SMILES

CC(=O)OC=C

InChI Identifier

InChI=1S/C4H6O2/c1-3-6-4(2)5/h3H,1H2,2H3

InChI Key

XTXRWKRVRITETP-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as enol esters. These are ester derivatives of enols. They have the general formula RC=COC(=O)R' where R, R' = H or organyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Enol esters

Alternative Parents

Substituents

Enol ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetate ester (CHEBI:46916 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-100°C
Boiling Point	Not Available
Solubility	20 mg/mL at 20°C

Predicted Properties

Property	Value	Source
Water Solubility	65.3 g/L	ALOGPS
logP	0.83	ALOGPS
logP	0.43	ChemAxon
logS	-0.12	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	21.1 m³·mol⁻¹	ChemAxon
Polarizability	8.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-822a98d017022e0d3838	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-822a98d017022e0d3838	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9000000000-efacbe718d07a50f11e2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-d776c53a3326ee70036f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-9000000000-4f9f09bebb037ead2596	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-4857aaa8b1d954975761	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-78aa34f58b412b0f8a68	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-9000000000-319f0beb68805dd151ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-3f182f981ecef4fccacd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052u-9000000000-55c887457fca16fe9537	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-8dffcb2ec574f759bccc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0007-9000000000-9db6245185c535efb6f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-65cd2a9c556e657f8c10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-98a0bebf5c7f9fa794e2	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-56392ad33ca543d33d88	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4) ; dermal (4)

Mechanism of Toxicity

One of the metabolites of vinyl acetate, acetaldehyde, is a known animal carcinogen. Acetaldehyde can form adducts with DNA, causing damage such as cross-links. (6, 1)

Metabolism

Vinyl acetate may be absorbed following ingestion, inhalation, or dermal exposure, and distributes throughout the body. It is rapidly hydrolyzed by esterases in the blood to acetate and the unstable intermediate, vinyl alcohol. Vinyl alcohol is then rapidly converted to acetaldehyde, which in turn is metabolized to acetate in the liver. This in turn is incorporated into the "2 carbon pool" of normal body metabolism and eventually forms carbon dioxide as the major breakdown product, which is expired. (6)

Toxicity Values

LD50: 2.92 g/kg (Oral, Rat) (8) LC50: 2511 ppm over 4 hours (Inhalation, Rabbit) (7)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (3)

Uses/Sources

Vinyl acetate is used mainly for the production of other industrial chemicals, such as polyvinyl acetate, an important polymer for which it is the precursor. These chemicals are used mainly to make glues for the packaging and building industries. They are also used to make paints, textiles, and paper. Vinyl acetate is also used as a coating in plastic films for food packaging and as a modifier of food starch. (5, 6)

Minimum Risk Level

Intermediate Inhalation: 0.01 ppm (2)

Health Effects

Vinyl acetate may affect the immune system. It may also be a carcinogen. (6)

Symptoms

Inhalation of vinyl acetate irritates the eyes, nose, and throat. Skin contact causes irritation and blisters. (6)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID