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Ethyl acetate (YMDB00569)

Identification
YMDB IDYMDB00569
NameEthyl acetate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionEthyl 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 exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Ethyl acetate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-acetoxyethane
  • ac. acetic ethyl ester
  • acetic acid ethyl ester
  • Acetic acid, ethyl ester
  • Acetic ester
  • Acetic ether
  • Acetidin
  • Acetoxyethane
  • Aethylacetat
  • CH3-CO-O-CH3
  • CH3COOC2H5
  • Essigsaeureethylester
  • Ethyl acetate
  • Ethyl acetic ester
  • Ethyl ethanoate
  • Ethylacetaat
  • Ethylacetat
  • Ethylazetat
  • Ethyle
  • Ethylester kyseliny octove
  • Etile
  • Vinegar naphtha
  • Acetyl ester
  • AcOEt
  • Essigester
  • EtOAc
  • Acetate ethyl ester
  • Acetate, ethyl ester
  • Ethyl ethanoic acid
  • Ethyl acetic acid
  • Acetic-acid-ethylester
  • Dibutylamine
  • Ethyl ester OF acetic acid
CAS number141-78-6
WeightAverage: 88.1051
Monoisotopic: 88.0524295
InChI KeyXEKOWRVHYACXOJ-UHFFFAOYSA-N
InChIInChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
IUPAC Nameethyl acetate
Traditional IUPAC Nameethyl acetate
Chemical FormulaC4H8O2
SMILESCCOC(C)=O
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
Physical Properties
StateLiquid
Charge0
Melting point-83.6 °C
Experimental Properties
PropertyValueReference
Water Solubility80 mg/mL at 25 oC [BANERJEE,S (1984)]PhysProp
LogP0.73 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility123 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
AniseFDB003240
BalsamFDB003240
EtherealFDB003240
FruityFDB003240
GreenFDB003240
PineappleFDB003240
SweetFDB003240
WeedyFDB003240
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Ethanol + Acetyl-CoA → Ethyl acetate + Coenzyme A
water + Ethyl acetate → Ethanol + Acetic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f48a6e770df57144ce33JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4fbfd506d2d6d053e57fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4950ee9233400dc5bfe6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-6209b0c76b2469152461JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f48a6e770df57144ce33JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4fbfd506d2d6d053e57fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4950ee9233400dc5bfe6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-6209b0c76b2469152461JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-02a908aacbb859e863a6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-f63aacf19cf8128e45b7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-2f521fd52e7d4d4ca892JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0204-9000000000-ac5b9c25d1bbbc164b29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-0e2695334ff196319a22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-e76a0fdf754f6a64b87dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-3ac243b7106e4fd2963cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-d24572f8800bb077f98aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-87bbaed151efac084591JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-87bbaed151efac084591JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e67f2acdbf749024e916JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-000dcb6fa74327b50a3bJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Fukuda, K., Kiyokawa, Y., Yanagiuchi, T., Wakai, Y., Kitamoto, K., Inoue, Y., Kimura, A. (2000). "Purification and characterization of isoamyl acetate-hydrolyzing esterase encoded by the IAH1 gene of Saccharomyces cerevisiae from a recombinant Escherichia coli." Appl Microbiol Biotechnol 53:596-600.10855721
  • Verstrepen, K. J., Van Laere, S. D., Vanderhaegen, B. M., Derdelinckx, G., Dufour, J. P., Pretorius, I. S., Winderickx, J., Thevelein, J. M., Delvaux, F. R. (2003). "Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters." Appl Environ Microbiol 69:5228-5237.12957907
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27750
HMDB IDHMDB0031217
Pubchem Compound ID8857
Kegg IDC00849
ChemSpider ID8525
FOODB IDFDB003240
WikipediaEthyl_acetate
BioCyc IDNot Available

Enzymes

Protein Details
1. Alcohol O-acetyltransferase 1
General function:
Involved in alcohol O-acetyltransferase activity
Specific function:
Catalyzes the esterification of isoamyl alcohol and various other alcohols by acetyl-CoA
Gene Name:
ATF1
Uniprot ID:
P40353
Molecular weight:
61035.5
Reactions
Acetyl-CoA + an alcohol → CoA + an acetyl ester.
Protein Details
2. Alcohol O-acetyltransferase 2
General function:
Involved in alcohol O-acetyltransferase activity
Specific function:
Acetyl-CoA + an alcohol = CoA + an acetyl ester
Gene Name:
ATF2
Uniprot ID:
P53296
Molecular weight:
61897.5
Reactions
Acetyl-CoA + an alcohol → CoA + an acetyl ester.
Protein Details
3. Isoamyl acetate-hydrolyzing esterase
General function:
Involved in hydrolase activity
Specific function:
Plays a crucial role in the hydrolysis of isoamyl acetate in sake mash
Gene Name:
IAH1
Uniprot ID:
P41734
Molecular weight:
27346.0
Reactions