phenethyl acetate (YMDB00574)

Identification
YMDB IDYMDB00574
Namephenethyl acetate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-Phenylethyl acetate is formed when the acetyl group of acetyl-CoA is transferred to 2-phenylethanol by an alcohol acetyltransferase. This reaction regenerates the levels of CoA in the cell and allows the removal of 2-phenylethanol (a byproduct of phenylalanine metabolism) from the cell as 2-phenylethyl acetate. In wine-making, the production of 2-phenylethyl acetate by yeast cells is responsible for a fruity, flowery flavor.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • β-Phenethyl acetate
  • β-Phenylethyl acetate
  • 2-Phenethyl acetate
  • 2-Phenylethyl acetate
  • Acetic acid beta-phenylethyl ester
  • acetic acid, 2-phenylethyl ester
  • Acetic acid, phenethyl ester
  • Benzylcarbinyl acetate
  • beta-Phenethyl acetate
  • beta-Phenylethyl acetate
  • Ethanol, 2-phenyl-, acetate
  • Phenethyl acetate
  • phenethyl alcohol, acetate
  • Phenylethyl acetate
  • Phenylethyl acetate-&beta
  • Phenylethyl acetate-beta
  • 2-Phenethyl acetic acid
  • Acetate b-phenylethyl ester
  • Acetate beta-phenylethyl ester
  • Acetate β-phenylethyl ester
  • Acetic acid b-phenylethyl ester
  • Acetic acid β-phenylethyl ester
  • Acetate, 2-phenylethyl ester
  • Acetate, phenethyl ester
  • Benzylcarbinyl acetic acid
  • b-Phenethyl acetate
  • b-Phenethyl acetic acid
  • beta-Phenethyl acetic acid
  • Β-phenethyl acetate
  • Β-phenethyl acetic acid
  • b-Phenylethyl acetate
  • b-Phenylethyl acetic acid
  • beta-Phenylethyl acetic acid
  • Β-phenylethyl acetate
  • Β-phenylethyl acetic acid
  • Phenethyl alcohol, acetic acid
  • 2-Phenylethyl acetic acid
  • 2-Phenylethyl acetate, 9ci
  • Acetic acid beta -phenylethyl ester
  • beta -Phenethyl acetate
  • beta -Phenylethyl acetate
  • FEMA 2857
  • Phenethyl acetic acid
CAS number103-45-7
WeightAverage: 164.2011
Monoisotopic: 164.083729628
InChI KeyMDHYEMXUFSJLGV-UHFFFAOYSA-N
InChIInChI=1S/C10H12O2/c1-9(11)12-8-7-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3
IUPAC Name2-phenylethyl acetate
Traditional IUPAC Namephenethyl acetate
Chemical FormulaC10H12O2
SMILESCC(=O)OCCC1=CC=CC=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-31.1 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP2.30 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.38ALOGPS
logP1.94ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity46.78 m³·mol⁻¹ChemAxon
Polarizability18.16 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
FloralFDB012153
FruityFDB012153
HoneyFDB012153
RoseFDB012153
SweetFDB012153
TobaccoFDB012153
TropicalFDB012153
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Acetyl-CoA + 2-phenylethanol → phenethyl acetate + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9700000000-7f41ba98b537cb7cccbbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-7900000000-952d038ccd29fcd2a3f2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-9700000000-b8614ae98ed2ee102473JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6x-9600000000-aeee3186e3cf069e2ea0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-4900000000-4c2bc6e2ddf9cc5d80cdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9700000000-7f41ba98b537cb7cccbbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-7900000000-952d038ccd29fcd2a3f2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-9700000000-b8614ae98ed2ee102473JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6x-9600000000-aeee3186e3cf069e2ea0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-4900000000-4c2bc6e2ddf9cc5d80cdJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-5097518360999245ecf3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-95adbd07b943670352f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-ddb144347ea8c19f00e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9700000000-dac196c84ec44ca106d8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-95adbd07b943670352f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-ddb144347ea8c19f00e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9700000000-dac196c84ec44ca106d8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4900000000-5c4930d450c32572502aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-395f138ac9ca21cc8e7eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-44e8d7eea55edf0201a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4900000000-5c4930d450c32572502aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-395f138ac9ca21cc8e7eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-44e8d7eea55edf0201a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-1b234ce3a2fda0adcf5eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-f251b49599f6045e682aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1900000000-a0fc8ff6174f0b2b0919JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-5900000000-a85cf40ee4556e18728fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9200000000-c9f467b09ec0ef6a5412JSpectraViewer
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
  • Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID31988
HMDB IDHMDB0033945
Pubchem Compound ID7654
Kegg IDC12303
ChemSpider ID21105987
FOODB IDFDB012153
Wikipedia IDNot Available
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.