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Record Information
Version2.0
Creation Date2009-07-30 17:56:29 UTC
Update Date2014-12-24 20:26:00 UTC
Accession NumberT3D3216
Identification
Common NameEthyl acrylate
ClassSmall Molecule
DescriptionEthyl 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.
Compound Type
  • Ester
  • Ether
  • Food Toxin
  • Fragrance Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Pollutant
Chemical Structure
Thumb
Synonyms
Synonym
2-Propenoic acid ethyl ester
2-Propenoic acid, ethyl ester
2-Propenoic acid, ethyl ester, homopolymer
Acrylic acid ethyl ester
Acrylic acid, ethyl ester
Acrylic acid, ethyl ester (inhibited)
Aethylacrylat
Akrylanem etylu
Carboset 511
CH2=CHCOOC2H5
Ethoxycarbonylethylene
Ethyl 2-propenoate
Ethyl 2-propenoate, homopolymer
Ethyl acrylate (inhibited)
Ethyl acrylate homopolymer
Ethyl acrylate polymer
Ethyl acrylate, inhibited
Ethyl acrylic acid
Ethyl ester of 2-propenoic acid
Ethyl propenoate
Ethyl propenoate, inhibited
Ethylacrylaat
Ethylakrylat
Ethylester kyseliny akrylove
Etil acrilato
Etilacrilatului
Etilacrilatului(roumanian)
FEMA 2418
Poly(acrylic acid, ethyl ester)
Poly(ethyl acrylate)
Polyethylacrylate
Propenoic acid,ethyl ester (ethylacrylate)
Chemical FormulaC5H8O2
Average Molecular Mass100.116 g/mol
Monoisotopic Mass100.052 g/mol
CAS Registry Number140-88-5
IUPAC Nameethyl prop-2-enoate
Traditional Nameethyl acrylate
SMILESCCOC(=O)C=C
InChI IdentifierInChI=1S/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3
InChI KeyInChIKey=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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAcrylic acids and derivatives
Direct ParentAcrylic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceClear liquid (7).
Experimental Properties
PropertyValue
Melting Point-71.2°C
Boiling Point99.4°C (210.9°F)
Solubility15 mg/mL at 25°C
LogP1.32
Predicted Properties
PropertyValueSource
Water Solubility38.8 g/LALOGPS
logP1.24ALOGPS
logP1.27ChemAxon
logS-0.41ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.81 m³·mol⁻¹ChemAxon
Polarizability10.5 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-8762b44567cd7afeb692JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-9000000000-25b2b71f04040f0959ddJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-9fb2ce6a8c6e827cca22JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-96cab8193fbae26c0e12JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-8762b44567cd7afeb692JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-9000000000-25b2b71f04040f0959ddJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-9fb2ce6a8c6e827cca22JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-96cab8193fbae26c0e12JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-b44a167f27a11982ce88JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-6900000000-afe7a2cd2b3f23523df8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200000000-b2987d0fef61f6de593eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-63a2abd18e012c3564b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-9000000000-b878ab9b418ac14be652JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-9000000000-75144951146aefa9cb6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9000000000-e6c22ca53e8d3d79f0b3JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-200bb2f29d9c1c5820c7JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureInhalation (7) ; oral (7) ; dermal (7) ; eye contact (7).
Mechanism of ToxicityEthyl 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 (2).
MetabolismEthyl 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 ValuesLD50: 760-1020 mg/kg (Oral, Rat) (8) LC50: 1000-2000 ppm over 4 hours (Inhalation, Rat) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (14)
Uses/SourcesEthyl acrylate is used in the production of polymers including resins, plastics, rubber, and denture material (15).
Minimum Risk LevelNot Available
Health EffectsThickened 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 (17).
SymptomsLethargy 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 (9, 7).
TreatmentFor 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. (5)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB33978
PubChem Compound ID8821
ChEMBL IDCHEMBL52084
ChemSpider ID8490
KEGG IDC19238
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDCPD-8095
CTD IDNot Available
Stitch IDEthyl acrylate
PDB IDNot Available
ACToR ID593
Wikipedia LinkEthyl_acrylate
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Miller RR, Ayres JA, Rampy LW, McKenna MJ: Metabolism of acrylate esters in rat tissue homogenates. Fundam Appl Toxicol. 1981 Nov-Dec;1(6):410-4. [7185591 ]
  2. Ghanayem BI, Maronpot RR, Matthews HB: Ethyl acrylate-induced gastric toxicity. II. Structure-toxicity relationships and mechanism. Toxicol Appl Pharmacol. 1985 Sep 15;80(2):336-44. [4024123 ]
  3. Inoue K: [Analysis and its application for prevention of side-effects of drugs and for evaluation of drug responsiveness]. Yakugaku Zasshi. 2004 Jun;124(6):293-9. [15170064 ]
  4. Klaassen A, Glykys J, Maguire J, Labarca C, Mody I, Boulter J: Seizures and enhanced cortical GABAergic inhibition in two mouse models of human autosomal dominant nocturnal frontal lobe epilepsy. Proc Natl Acad Sci U S A. 2006 Dec 12;103(50):19152-7. Epub 2006 Dec 4. [17146052 ]
  5. Gidlof AC, Ocaya P, Olofsson PS, Torma H, Sirsjo A: Differences in retinol metabolism and proliferative response between neointimal and medial smooth muscle cells. J Vasc Res. 2006;43(4):392-8. Epub 2006 Jul 6. [16837774 ]
  6. American Conference of Governmental Industrial Hygienists, Inc. (1991). Documentation of the Threshold Limit Values and Biological Exposure Indices. 6th ed. Volumes I, II, III. Cincinnati, OH: American Conference of Governmental Industrial Hygienists.
  7. Clayton GD and Clayton FE (eds) (1993-1994). Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc.
  8. Kirk-Othmer Encyclopedia of Chemical Technology (1978-1984). 3rd ed. Volumes 1-26. New York, NY: John Wiley and Sons.
  9. The Merck Index (1983). The Merck Index. 10th ed. Rahway, New Jersey: Merck Co., Inc.
  10. Bronstein, AC, Currance PL (1994). Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994.
  11. IARC (1986). Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-Present. (Multivolume work).
  12. National Toxicology Program (1986). Fiscal Year 1986 Annual Plan.
  13. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  14. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  15. Quantyka (2008). Safety Data Sheet for 4-Allylanisole. [Link]
  16. Wikipedia. Ethyl Acrylate. Last Updated 20 July 2009. [Link]
  17. Technology Transfer Network, Air Toxics Web Site (2009). Ethyl Acrylate. [Link]
  18. IARC (1986). Monograph of Ethyl Acrylate. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available