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Identification
YMDB IDYMDB01477
NameOctyl acetate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionOctyl acetate, also known as octyl ethanoate or 1-octanol acetate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Octyl acetate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • 1-Octanol acetate
  • 1-Octyl acetate
  • Acetate C-8
  • ACETATE ION
  • Acetic acid n-octyl ester
  • acetic acid, ion(1-)
  • Acetic acid, octyl ester
  • Caprylyl acetate
  • CH3-COO(-)
  • Ethanoat
  • ethanoate
  • MeCO2 anion
  • n-Octanyl acetate
  • n-Octyl acetate
  • n-Octyl ethanoate
  • Octanol acetate
  • Octyl acetate (VAN)
  • Octyl alcohol acetate
  • Octyl ethanoate
  • Caprylyl acetic acid
  • N-Octanyl acetic acid
  • Octyl ethanoic acid
  • Octyl acetic acid
  • 2-Ethylhexyl acetate
  • Acetic acid octyl ester
  • FEMA 2806
  • Octyl acetate, normal
CAS number112-14-1
WeightAverage: 172.2646
Monoisotopic: 172.146329884
InChI KeyYLYBTZIQSIBWLI-UHFFFAOYSA-N
InChIInChI=1S/C10H20O2/c1-3-4-5-6-7-8-9-12-10(2)11/h3-9H2,1-2H3
IUPAC Nameoctyl acetate
Traditional IUPAC Nameoctyl acetate
Chemical FormulaC10H20O2
SMILESCCCCCCCCOC(C)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohol esters
Direct ParentFatty alcohol esters
Alternative Parents
Substituents
  • Fatty alcohol ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • 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-38.5 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP4.12ALOGPS
logP3.02ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.69 m³·mol⁻¹ChemAxon
Polarizability21.67 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
EarthyFDB017993
GreenFDB017993
HerbalFDB017993
MushroomFDB017993
WaxyFDB017993
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-a81fd8b1966f2694f866JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-ad8f2fb68399e500c0c0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06zc-9000000000-06f9431c8788ad124bc0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00di-0900000000-e264fc6a084c268fd0a9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-699c43ddb8113422b57cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-a81fd8b1966f2694f866JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-ad8f2fb68399e500c0c0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06zc-9000000000-06f9431c8788ad124bc0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00di-0900000000-e264fc6a084c268fd0a9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-699c43ddb8113422b57cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-d6b38fed7584c47715bfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-8b1904c66840d99f0149JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4900000000-acd5372ebeefeda06075JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-6fd144c97864a0a1a09eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-4900000000-963a79288ee88b4a6ea0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-1260e6fabd60560129e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-4557d26ca4723c7f500eJSpectraViewer
References
References:
  • 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
  • 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
  • Mulet, J. M., Alemany, B., Ros, R., Calvete, J. J., Serrano, R. (2004). "Expression of a plant serine O-acetyltransferase in Saccharomyces cerevisiae confers osmotic tolerance and creates an alternative pathway for cysteine biosynthesis." Yeast 21:303-312.15042590
  • Paiva, S., Devaux, F., Barbosa, S., Jacq, C., Casal, M. (2004). "Ady2p is essential for the acetate permease activity in the yeast Saccharomyces cerevisiae." Yeast 21:201-210.14968426
  • Saint-Prix, F., Bonquist, L., Dequin, S. (2004). "Functional analysis of the ALD gene family of Saccharomyces cerevisiae during anaerobic growth on glucose: the NADP+-dependent Ald6p and Ald5p isoforms play a major role in acetate formation." Microbiology 150:2209-2220.15256563
  • Watanabe, R., Ohishi, K., Maeda, Y., Nakamura, N., Kinoshita, T. (1999). "Mammalian PIG-L and its yeast homologue Gpi12p are N-acetylglucosaminylphosphatidylinositol de-N-acetylases essential in glycosylphosphatidylinositol biosynthesis." Biochem J 339 ( Pt 1):185-192.10085243
  • 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
  • Buu, L. M., Chen, Y. C., Lee, F. J. (2003). "Functional characterization and localization of acetyl-CoA hydrolase, Ach1p, in Saccharomyces cerevisiae." J Biol Chem 278:17203-17209.12606555
  • van den Berg, M. A., de Jong-Gubbels, P., Kortland, C. J., van Dijken, J. P., Pronk, J. T., Steensma, H. Y. (1996). "The two acetyl-coenzyme A synthetases of Saccharomyces cerevisiae differ with respect to kinetic properties and transcriptional regulation." J Biol Chem 271:28953-28959.8910545
  • Takahashi, H., McCaffery, J. M., Irizarry, R. A., Boeke, J. D. (2006). "Nucleocytosolic acetyl-coenzyme a synthetase is required for histone acetylation and global transcription." Mol Cell 23:207-217.16857587
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID87495
HMDB IDHMDB0038602
Pubchem Compound ID8164
Kegg IDNot Available
ChemSpider ID7872
FOODB IDFDB017993
WikipediaOctyl_acetate
BioCyc IDNot Available

Enzymes

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.
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.