ContaminantDB: Ethyl acrylate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:56:29 UTC

Update Date

2026-03-27 00:45:33 UTC

Accession Number

CHEM002448

Identification

Common Name

Ethyl acrylate

Class

Small Molecule

Description

Ethyl acrylate is found in pineapple. Ethyl acrylate is a flavouring ingredient Although there are some reports claiming that ethyl acrylate is a carcinogen, major respected bodies regard the evidence of human carcinogenicity as weak and/or inconsistent. The International Agency for Research on Cancer stated, Overall evaluation, Ethyl acrylate is possibly carcinogenic to humans (Group 2B). The United States Environmental Protection Agency (EPA) states, Human studies on occupational exposure to ethyl acrylate… have suggested a relationship between exposure to the chemical(s) and colorectal cancer, but the evidence is conflicting and inconclusive. In a study by the National Toxicology Program (NTP), increased incidences of squamous cell papillomas and carcinomas of the forestomach were observed in rats and mice exposed via gavage (experimentally placing the chemical in the stomach). However, the NTP recently determined that these data were not relevant to human carcinogenicity and removed ethyl acrylate from its list of carcinogens. (Occupational exposure generally involves exposure that occurs regularly, over an extended period of time). Ethyl acrylate is an organic compound primarily used in the preparation of various polymers. It is a clear liquid with an acrid penetrating odor. The human nose is capable of detecting this odor at a thousand times lower concentration then is considered harmful if continuously exposed for some period of time.

Contaminant Sources

Clean Air Act Chemicals
EAFUS Chemicals
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 2B
IARC Carcinogens Group 3
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ester
Ether
Food Toxin
Fragrance Toxin
Household Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin
Pollutant

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ethyl acrylic acid	Generator
2-Propenoic acid ethyl ester	HMDB
2-Propenoic acid, ethyl ester	HMDB
2-Propenoic acid, ethyl ester, homopolymer	HMDB
Acrylic acid ethyl ester	HMDB, MeSH
Acrylic acid, ethyl ester	HMDB
Acrylic acid, ethyl ester (inhibited)	HMDB
Aethylacrylat	HMDB
Akrylanem etylu	HMDB
Carboset 511	HMDB
CH2=chcooc2h5	HMDB
Ethoxycarbonylethylene	HMDB
Ethyl 2-propenoate	HMDB
Ethyl 2-propenoate, homopolymer	HMDB
Ethyl acrylate (inhibited)	HMDB
Ethyl acrylate homopolymer	HMDB
Ethyl acrylate polymer	HMDB
Ethyl acrylate, inhibited	HMDB
Ethyl ester OF 2-propenoic acid	HMDB
Ethyl propenoate	HMDB
Ethyl propenoate, inhibited	HMDB
Ethylacrylaat	HMDB
Ethylakrylat	HMDB
Ethylester kyseliny akrylove	HMDB
Etil acrilato	HMDB
Etilacrilatului	HMDB
Etilacrilatului(roumanian)	HMDB
FEMA 2418	HMDB
Poly(acrylic acid, ethyl ester)	HMDB
Poly(ethyl acrylate)	HMDB
Polyethylacrylate	HMDB
Propenoic acid,ethyl ester (ethylacrylate)	HMDB
Ethyl 2E-propenoic acid	Generator
Ethyl acrylate	MeSH

Chemical Formula

C₅H₈O₂

Average Molecular Mass

100.116 g/mol

Monoisotopic Mass

100.052 g/mol

CAS Registry Number

140-88-5

IUPAC Name

ethyl prop-2-enoate

Traditional Name

ethyl acrylate

SMILES

CCOC(=O)C=C

InChI Identifier

InChI=1S/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3

InChI Key

JIGUQPWFLRLWPJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acrylic acid esters. These are organic compounds containing and ester acrylic acid (CH2=CHC(=O)OH).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Acrylic acids and derivatives

Direct Parent

Acrylic acid esters

Alternative Parents

Substituents

Acrylic acid ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid 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

enoate ester (CHEBI:82327 )
Wax monoesters (LMFA07010505 )

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

Clear liquid (12).

Experimental Properties

Property	Value
Melting Point	-71.2°C
Boiling Point	99.4°C (210.9°F)
Solubility	15 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	38.8 g/L	ALOGPS
logP	1.24	ALOGPS
logP	1.27	ChemAxon
logS	-0.41	ALOGPS
pKa (Strongest Basic)	-6.8	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	3	ChemAxon
Refractivity	26.81 m³·mol⁻¹	ChemAxon
Polarizability	10.5 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)	splash10-0a4i-9000000000-8762b44567cd7afeb692	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-9000000000-25b2b71f04040f0959dd	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-9fb2ce6a8c6e827cca22	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-96cab8193fbae26c0e12	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-8762b44567cd7afeb692	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-9000000000-25b2b71f04040f0959dd	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-9fb2ce6a8c6e827cca22	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-96cab8193fbae26c0e12	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-b44a167f27a11982ce88	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	splash10-0udi-6900000000-afe7a2cd2b3f23523df8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9200000000-b2987d0fef61f6de593e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-63a2abd18e012c3564b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-9000000000-b878ab9b418ac14be652	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-9000000000-75144951146aefa9cb6c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-9000000000-e6c22ca53e8d3d79f0b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-47264722dae793143c2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9000000000-7bd873751816c51e989f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-55bfb6f6731ad493ad1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-6636b98068f5d8e94960	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-9000000000-e0f16a81ce309da5b9a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-e973a9ae833442ead826	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9000000000-200bb2f29d9c1c5820c7	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
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (12) ; oral (12) ; dermal (12) ; eye contact (12).

Mechanism of Toxicity

Ethyl acrylate causes gastric lesions depending upon upon the rate of chemical delivery to stomach tissue as a result of interaction of the parent molecule or metabolites (other than hydrolysis products), with subcellular sites in stomach tissue (5).

Metabolism

Ethyl acrylate is hydrolized to acrylic acid in liver, kidney, and lung homogenates. It is suggested to bind to glutathione spontaneaoulsy and after catalysis by liver glutathione-S-transferase. The major metabolites of ethyl acrylate are mercapturic acids od ethyl acrylate and acrylic acid. Three metabolites were identified in a study: 3-hydroxypropionic acid and two mercapturic acids. N-Acetyl-S-(2-carboxyethyl)cysteine arises by glutathione conjugation of acrylic acid, while N-acetyl-S-(2-carboxyethyl)cysteine ethyl ester derives from the conjugation of intact ethyl acrylate.(1, 3, 4).

Toxicity Values

LD50: 760-1020 mg/kg (Oral, Rat) (13) LC50: 1000-2000 ppm over 4 hours (Inhalation, Rat) (11)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (6)

Uses/Sources

Ethyl acrylate is used in the production of polymers including resins, plastics, rubber, and denture material (7).

Minimum Risk Level

Not Available

Health Effects

Thickened forestomach mucosa, forestomach inflammation and lesions, and abdominal adhesions; swelling of renal tubules and the liver, minor lesions on the liver and lung, and increased kidney weight may result from poisoning (9).

Symptoms

Lethargy and convulsions may occur if vapors are inhaled in high concentrations. Ethyl acrylate is irritating to the mucous membranes of the gastrointestinal tract and respiratory system. Prolonged exposure may produce drowsiness, headache and nausea . Iching of the skin and the face can also occur (14, 12).

Treatment

For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport. Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal. (2)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0033978

FooDB ID

FDB012210

Phenol Explorer ID

Not Available

KNApSAcK ID