Record Information
Version1.0
Created at2020-03-19 00:51:32 UTC
Updated at2020-12-07 19:07:41 UTC
CannabisDB IDCDB000693
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameEthyl acetate
DescriptionAcetic acid-ethyl ester or ethyl acetate, also known as 1-acetoxyethane or acetic ester, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Ethyl acetate is a clear, colorless liquid. It is an ester of acetic acid and ethanol. It is found in essentially all organisms, from bacteria to yeast, to plants to humans. Ethyl acetate has an ethereal, sweet or fruity odor with a sweet, grape or cherry taste. Ethyl acetate is present in confectionery (it is used in artificial fruit essences), perfumes, and fruits. In perfumes, it evaporates quickly, leaving only the scent of the perfume on the skin. Ethyl acetate is found in many fruits such as pineapples, and sweet oranges and in a lower concentration in safflowers. Ethyl acetate has also been found in Cannabis sativa (PMID: 6991645 , 26657499 ). It has also been detected, but not quantified in, several different foods, such as oxheart cabbages, agaves, chervils, peaches (var.), cereal crops, radishes, fruit juices, beer, wine, spirits etc. Ethyl acetate is the most common ester in wine, being the product of acetic acid and ethanol generated during fermentation. The aroma of ethyl acetate is most intense in younger wines and contributes towards the general perception of 'fruitiness' in wine. Industrially, it is used as a solvent in glues, nail polish removers, and in the decaffeination process of tea and coffee. It is widely used as an organic solvent because of its low cost, low toxicity, and agreeable odor. It is also used in paints as an activator or hardener and for colour and inks used to mark fruit or vegetables. In the field of entomology, ethyl acetate is an effective asphyxiant for use in insect collecting and study. Because it is not hygroscopic, ethyl acetate also keeps the insect soft enough to allow proper mounting suitable for a collection. In a killing jar charged with ethyl acetate, the vapors will kill the collected (usually adult) insect quickly without destroying it. Ethyl acetate has very low toxicity, however overexposure to ethyl acetate may cause irritation of the eyes, nose, and throat.
Structure
Thumb
Synonyms
ValueSource
1-AcetoxyethaneChEBI
Acetic acid ethyl esterChEBI
Acetic acid, ethyl esterChEBI
Acetic esterChEBI
AcetoxyethaneChEBI
Acetyl esterChEBI
AcOEtChEBI
CH3-CO-O-CH3ChEBI
EssigesterChEBI
EssigsaeureethylesterChEBI
Ethyl acetic esterChEBI
Ethyl ethanoateChEBI
EthylacetatChEBI
EthylazetatChEBI
EtOAcChEBI
Vinegar naphthaChEBI
Acetate ethyl esterGenerator
Acetate, ethyl esterGenerator
Ethyl ethanoic acidGenerator
Ethyl acetic acidGenerator
Acetic etherHMDB
Acetic-acid-ethylesterHMDB
AcetidinHMDB
DibutylamineHMDB
Ethyl ester OF acetic acidHMDB
Chemical FormulaC4H8O2
Average Molecular Weight88.11
Monoisotopic Molecular Weight88.0524
IUPAC Nameethyl acetate
Traditional Nameethyl acetate
CAS Registry Number141-78-6
SMILES
CCOC(C)=O
InChI Identifier
InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
InChI KeyXEKOWRVHYACXOJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic acid esters
Alternative Parents
Substituents
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-83.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility80 mg/mL at 25 °CNot Available
logP0.73Not Available
Predicted Properties
PropertyValueSource
logP0.74ALOGPS
logP0.28ChemAxon
logS0.14ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.16 m³·mol⁻¹ChemAxon
Polarizability9.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-000dcb6fa74327b50a3b2014-09-20View Spectrum
GC-MSEthylacetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-f48a6e770df57144ce33Spectrum
GC-MSEthylacetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4fbfd506d2d6d053e57fSpectrum
GC-MSEthylacetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4950ee9233400dc5bfe6Spectrum
GC-MSEthylacetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-6209b0c76b2469152461Spectrum
GC-MSEthylacetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-f48a6e770df57144ce33Spectrum
GC-MSEthylacetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4fbfd506d2d6d053e57fSpectrum
GC-MSEthylacetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4950ee9233400dc5bfe6Spectrum
GC-MSEthylacetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-6209b0c76b2469152461Spectrum
Predicted GC-MSEthylacetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-9000000000-02a908aacbb859e863a6Spectrum
Predicted GC-MSEthylacetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-f63aacf19cf8128e45b72015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-2f521fd52e7d4d4ca8922015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0204-9000000000-ac5b9c25d1bbbc164b292015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-0e2695334ff196319a222015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-e76a0fdf754f6a64b87d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-3ac243b7106e4fd2963c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-d24572f8800bb077f98a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-87bbaed151efac0845912021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-87bbaed151efac0845912021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e67f2acdbf749024e9162021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0031217
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003240
KNApSAcK IDC00001308
Chemspider ID8525
KEGG Compound IDC00849
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl_acetate
METLIN IDNot Available
PubChem Compound8857
PDB IDEEE
ChEBI ID27750
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]