Showing Compound Card for Methyl acetate (CDB000095)

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Record Information
Version1.0
Created at2020-03-18 23:24:35 UTC
Updated at2020-12-07 19:07:06 UTC
CannabisDB IDCDB000095
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethyl acetate
DescriptionAcetic acid-methyl ester or methyl acetate, also known as devoton, methyl ethanoate or tereton, belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group. It is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. Specifically methyl acetate has a sweet, fruity, cognac or rum-like aroma and a green, fruity taste. Methyl acetate is a flavouring agent and can be found naturally in many fruits, some of which include apple, grape, banana, orange mint, and ginger. Methyl acetate has also been found in Cannabis sativa (PMID: 6991645 , 26657499 ). It is also used as a perfuming agent in the cosmetic industry. Methyl acetate has characteristics very similar to its analog ethyl acetate. As a result, methyl acetate is used as a solvent in glues, paints, and nail polish removers, in chemical reactions, and for extractions. As an extraction solvent, methyl acetate is a non-polar (lipophilic) to weakly polar (hydrophilic) aprotic solvent. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperatures its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or acids. Methyl acetate is an ester that can be synthesized from acetic acid and methanol in the presence of strong acids such as sulfuric acid in an esterification reaction. In the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid it is hydrolyzed back into methanol and acetic acid, especially at elevated temperature.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Acetate de methyleChEBI
Acetic acid methyl esterChEBI
AcOMeChEBI
CH3CO2CH3ChEBI
CH3COOCH3ChEBI
DevotonChEBI
MeOAcChEBI
Methyl ethanoateChEBI
MethylacetatChEBI
TeretonChEBI
Acetic acid de methyleGenerator
Acetate methyl esterGenerator
Methyl ethanoic acidGenerator
Methyl acetic acidGenerator
Acetic acid, methyl esterHMDB
Acetic acid,methyl esterHMDB
Ethyl ester OF monoacetic acidHMDB
FEMA 2676HMDB
HSDB 95HMDB
METHYL acetATE, 97%HMDB
Methyl acetic esterHMDB
Methyl ester OF acetic acidHMDB
Methyl-acetateHMDB
MethylacetaatHMDB
Methyle (acetate de)HMDB
Methylester kiseliny octoveHMDB
MetileHMDB
Metile (acetato di)HMDB
Octan metyluHMDB
Chemical FormulaC3H6O2
Average Molecular Weight74.08
Monoisotopic Molecular Weight74.0368
IUPAC Namemethyl acetate
Traditional Namemethyl acetate
CAS Registry Number79-20-9
SMILES
COC(C)=O
InChI Identifier
InChI=1S/C3H6O2/c1-3(4)5-2/h1-2H3
InChI KeyKXKVLQRXCPHEJC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentMethyl esters
Alternative Parents
Substituents
  • Methyl 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

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-98.7 °CNot Available
Boiling Point56.9 °CWikipedia
Water Solubility243 mg/mL at 20 °CNot Available
logP0.18Not Available
Predicted Properties
PropertyValueSource
logP0.18ALOGPS
logP-0.077ChemAxon
logS0.54ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.41 m³·mol⁻¹ChemAxon
Polarizability7.36 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-b1ba1d5d07d16b762fc52015-03-01View Spectrum
GC-MSMethyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4756b467f06f20361e44Spectrum
GC-MSMethyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-5159f548daf4863c7b5fSpectrum
GC-MSMethyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-8e16bef1c0d338a20817Spectrum
GC-MSMethyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4756b467f06f20361e44Spectrum
GC-MSMethyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-5159f548daf4863c7b5fSpectrum
GC-MSMethyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-8e16bef1c0d338a20817Spectrum
Predicted GC-MSMethyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9000000000-2e654baf975da65a4e69Spectrum
Predicted GC-MSMethyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-9000000000-b1f6888fe1c824f0554a2020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-b2ff0c2f4a7b9a3ec3802016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-b923d9ac4ee5f8a0dc112016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5281419eb66f1a975c162016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-6fa6e544dfea79b0c7702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-bfa93bd1d3be434922762016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-edf31adaab90917da7812016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-a18665b48b96b6efae4c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9000000000-c017bec70f7f1f943e1c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-38f5194f74dd1669b1f72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-6ec74bc1ba5c32a6e9ad2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-0825639de956c49337542021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-87bbaed151efac0845912021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)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 IDHMDB0031523
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008125
KNApSAcK IDC00048479
Chemspider ID6335
KEGG Compound IDC17530
BioCyc IDMETHYL-ACETATE
BiGG IDNot Available
Wikipedia LinkMethyl_acetate
METLIN IDNot Available
PubChem Compound6584
PDB IDNot Available
ChEBI ID77700
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 ]