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Record Information
Version3.6
Creation Date2012-09-11 17:43:49 UTC
Update Date2016-02-11 02:00:15 UTC
HMDB IDHMDB31523
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethyl acetate
DescriptionMethyl acetate is found in apple. Methyl acetate is a flavouring ingredient. Methyl acetate is present in grape, banana and other fruits Methyl acetate is an ester that is 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. Methyl acetate, also known as acetic acid methyl ester or methyl ethanoate, is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. Methyl acetate has characteristics very similar to its analog ethyl acetate. Methyl acetate is used as a solvent in glues, paints, and nail polish removers, in chemical reactions, and for extractions. 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 temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or acids. Methyl acetate is VOC exempt. The conversion of methyl acetate back into its components, by an acid, is a first-order reaction with respect to the ester. The reaction of methyl acetate and a base, for example sodium hydroxide, is a second-order reaction with respect to both reactants. Methyl 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).
Structure
Thumb
Synonyms
ValueSource
Acetate de methyleChEBI
Acetic acid methyl esterChEBI
AcOMeChEBI
CH3CO2CH3ChEBI
CH3COOCH3ChEBI
DevotonChEBI
MeOAcChEBI
Methyl ethanoateChEBI
MethylacetatChEBI
TeretonChEBI
Acetic acid de methyleGenerator
Methyl acetic acidGenerator
Acetate methyl esterGenerator
Methyl ethanoic 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 Weight74.0785
Monoisotopic Molecular Weight74.036779436
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 KeyInChIKey=KXKVLQRXCPHEJC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetate salts. These are organic compounds containing acetic acid as its acid component.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentAcetate salts
Alternative Parents
Substituents
  • Acetate salt
  • Methyl ester
  • Carboxylic acid ester
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
BiofunctionNot Available
Application
  • Flavoring Agent
  • Laboratory Chemical
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point-98.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility243 mg/mL at 20 °CNot Available
LogP0.18Not Available
Predicted Properties
PropertyValueSource
Water Solubility259.0 mg/mLALOGPS
logP0.18ALOGPS
logP-0.077ChemAxon
logS0.54ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.41 m3·mol-1ChemAxon
Polarizability7.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-b1ba1d5d07d16b762fc5View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008125
KNApSAcK IDNot Available
Chemspider ID6335
KEGG Compound IDC17530
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl_acetate
NuGOwiki LinkHMDB31523
Metagene LinkHMDB31523
METLIN IDNot Available
PubChem Compound6584
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
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  3. Frank N, Caesar R, Scherf HR, Wiessler M: Influence of the carboxylesterase inhibitor bis-p-nitrophenylphosphate on the rates of hydrolysis of various alpha-esters of 1-(N-methyl-N-nitrosamino)-methanol in vitro and in vivo and on the acute toxicity and carcinogenicity of 1-(N-methyl-N-nitrosamino)-methylacetate. J Cancer Res Clin Oncol. 1986;111(2):98-102. [3700465 ]
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  8. Aleksandrov SL, Antonov VK: [Quantum chemistry analysis of the mechanism of action of proteolytic enzymes. II. Nucleophilic attack]. Mol Biol (Mosk). 1984 Nov-Dec;18(6):1576-82. [6097813 ]
  9. Navas PB: [Chemical composition of the virgin oil obtained by mechanical pressing form several grape seed varieties (Vitis vinifera L.) with emphasis on minor constituents]. Arch Latinoam Nutr. 2009 Jun;59(2):214-9. [19719020 ]
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  11. Caesar R, Frank N, Wiessler M: Stability of various alpha-esters of 1-(N-methyl-N-nitrosamino)-methanol in vitro and in vivo. Carcinogenesis. 1984 Oct;5(10):1231-4. [6548422 ]
  12. Qiu F, Taylor AW, Men S, Villar-Garcia IJ, Licence P: An ultra high vacuum-spectroelectrochemical study of the dissolution of copper in the ionic liquid (N-methylacetate)-4-picolinium bis(trifluoromethylsulfonyl)imide. Phys Chem Chem Phys. 2010 Feb 28;12(8):1982-90. doi: 10.1039/b924985k. Epub 2010 Jan 26. [20145868 ]
  13. Stamato FM, Longo E, Ferreira R, Tapia O: The catalytic mechanism of serine proteases. III. An Indo-ISCRF study of the methylacetate docking in alpha-chymotrypsin. J Theor Biol. 1986 Jan 7;118(1):45-59. [3754607 ]
  14. Naidoo S, Timiras PS: Effects of age on the metabolism of thyroid hormones by rat brain tissue in vitro. Dev Neurosci. 1979;2(5):213-24. [535533 ]
  15. Kim KH, Kim Y: Theoretical studies for Lewis acid-base interactions and C-H...O weak hydrogen bonding in various CO2 complexes. J Phys Chem A. 2008 Feb 21;112(7):1596-603. doi: 10.1021/jp709648q. Epub 2008 Jan 26. [18220375 ]
  16. Heitmann D, Lissel M, Kempken R, Muthing J: Replacement of chloroform throughout glycosphingolipid isolation. Biomed Chromatogr. 1996 Sep-Oct;10(5):245-50. [8879533 ]
  17. Agudoawu SA, Yiu SH, Wallace JL, Knaus EE: Synthesis and analgesic activity of 2-methyl-2-[1-(3-benzoyl-4-substituted-1,4-dihydropyridyl)]acetic acid methyl esters, acetic acids, and acetamides. Arch Pharm (Weinheim). 1999 Jun;332(6):213-8. [10399491 ]
  18. Mittal S, Malde A, Selvam C, Arun KH, Johar PS, Jachak SM, Ramarao P, Bharatam PV, Chawla HP: Synthesis and evaluation of S-4-(3-thienyl)phenyl-alpha-methylacetic acid. Bioorg Med Chem Lett. 2004 Feb 23;14(4):979-82. [15013005 ]
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  20. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.