Ethenyl acetate (T3D3470)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-30 17:58:33 UTC
Update Date2014-12-24 20:26:06 UTC
Accession NumberT3D3470
Identification
Common NameEthenyl acetate
ClassSmall Molecule
DescriptionPolyvinyl 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).
Compound Type
  • Cigarette Toxin
  • Ester
  • Food Toxin
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Lachrymator
  • Metabolite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
CH3CO2CH=CH2
Ethenyl acetate, 9CI
Ethenyl acetic acid
Everflex 81L
Unocal 76 Res 6206
Unocal 76 Res S-55
VAC
Vinile
Vinnapas A 50
Vinyl acetate
Vinyl ester of acetic acid
Vinyle
Chemical FormulaC4H6O2
Average Molecular Mass86.089 g/mol
Monoisotopic Mass86.037 g/mol
CAS Registry Number108-05-4
IUPAC Nameethenyl acetate
Traditional Namevinyl acetate
SMILESCC(=O)OC=C
InChI IdentifierInChI=1S/C4H6O2/c1-3-6-4(2)5/h3H,1H2,2H3
InChI KeyInChIKey=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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentEnol 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 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
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-100°C
Boiling PointNot Available
Solubility20 mg/mL at 20°C
LogP0.73
Predicted Properties
PropertyValueSource
Water Solubility65.3 g/LALOGPS
logP0.83ALOGPS
logP0.43ChemAxon
logS-0.12ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity21.1 m³·mol⁻¹ChemAxon
Polarizability8.57 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-822a98d017022e0d38382017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-822a98d017022e0d38382018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-efacbe718d07a50f11e22017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-d776c53a3326ee70036f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-9000000000-4f9f09bebb037ead25962016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4857aaa8b1d9549757612016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-78aa34f58b412b0f8a682016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-9000000000-319f0beb68805dd151ce2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-3f182f981ecef4fccacd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052u-9000000000-55c887457fca16fe95372021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-8dffcb2ec574f759bccc2021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-9000000000-9db6245185c535efb6f92021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-65cd2a9c556e657f8c102021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-98a0bebf5c7f9fa794e22021-09-25View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-56392ad33ca543d33d882014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
Toxicity Profile
Route of ExposureOral (9) ; inhalation (9) ; dermal (9)
Mechanism of ToxicityOne of the metabolites of vinyl acetate, acetaldehyde, is a known animal carcinogen. Acetaldehyde can form adducts with DNA, causing damage such as cross-links. (8, 1)
MetabolismVinyl 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. (8)
Toxicity ValuesLD50: 2.92 g/kg (Oral, Rat) (3) LC50: 2511 ppm over 4 hours (Inhalation, Rabbit) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (6)
Uses/SourcesVinyl 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. (7, 8)
Minimum Risk LevelIntermediate Inhalation: 0.01 ppm (5)
Health EffectsVinyl acetate may affect the immune system. It may also be a carcinogen. (8)
SymptomsInhalation of vinyl acetate irritates the eyes, nose, and throat. Skin contact causes irritation and blisters. (8)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31209
PubChem Compound ID7904
ChEMBL IDCHEMBL1470323
ChemSpider ID7616
KEGG IDC19309
UniProt IDNot Available
OMIM ID
ChEBI ID46916
BioCyc IDNot Available
CTD IDNot Available
Stitch IDVinyl acetate
PDB IDNot Available
ACToR ID1463
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3470.pdf
General References
  1. Brooks PJ, Theruvathu JA: DNA adducts from acetaldehyde: implications for alcohol-related carcinogenesis. Alcohol. 2005 Apr;35(3):187-93. [16054980 ]
  2. 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.
  3. Budavari, S (ed) (1989). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc.
  4. EAFUS: Everything Added to Food in the United States.
  5. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  6. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  7. Wikipedia. Vinyl acetate. Last Updated 26 July 2009. [Link]
  8. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for vinyl acetate. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  9. The Physical and Theoretical Chemistry Laboratory of Oxford University (2005). Material Safety Data Sheet (MSDS) for phenyl isothiocyanate. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]