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isobutyl acetate (YMDB00572)

Identification
YMDB IDYMDB00572
Nameisobutyl acetate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Methylpropyl acetate, also known as acetate d'isobutyle or essigsaeureisobutylester, 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). Based on a literature review very few articles have been published on 2-Methylpropyl acetate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • β-Methylpropyl ethanoate
  • 2-Methyl-1-propanol, acetate
  • 2-Methyl-1-propyl acetate
  • 2-Methylpropyl acetate
  • 2-Methylpropyl ethanoate
  • Acetate d'isobutyle
  • Acetic acid, 2-methylpropyl ester
  • Acetic acid, isobutyl ester
  • beta-Methylpropyl ethanoate
  • Essigsaeureisobutylester
  • i-Butyl acetate
  • isobutyl acetate
  • Isobutyl acetate fcc
  • Isobutyl ethanoate
  • Isobutylacetat
  • Isobutylazetat
  • Isobutylester kyseliny octove
  • 2-Methyl-1-propyl acetic acid
  • 2-Methylpropyl ethanoic acid
  • Acetic acid d'isobutyle
  • Acetate, 2-methylpropyl ester
  • Acetate, isobutyl ester
  • b-Methylpropyl ethanoate
  • b-Methylpropyl ethanoic acid
  • beta-Methylpropyl ethanoic acid
  • Β-methylpropyl ethanoate
  • Β-methylpropyl ethanoic acid
  • I-butyl acetic acid
  • Isobutyl ethanoic acid
  • 2-Methylpropyl acetic acid
  • 2-Methylpropyl acetate, 9ci
  • beta -Methylpropyl ethanoate
  • FEMA 2175
  • Isobutyl acetate, 8ci
  • Isobutyl acetic acid
  • Isobutylacetate
CAS number110-19-0
WeightAverage: 116.1583
Monoisotopic: 116.083729628
InChI KeyGJRQTCIYDGXPES-UHFFFAOYSA-N
InChIInChI=1S/C6H12O2/c1-5(2)4-8-6(3)7/h5H,4H2,1-3H3
IUPAC Name2-methylpropyl acetate
Traditional IUPAC Nameisobutyl acetate
Chemical FormulaC6H12O2
SMILESCC(C)COC(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-98.8 °C
Experimental Properties
PropertyValueReference
Water Solubility6.3 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.78 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.71 g/LALOGPS
logP1.74ALOGPS
logP1.17ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.16 m³·mol⁻¹ChemAxon
Polarizability13.11 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
AppleFDB003275
BananaFDB003275
BitterFDB003275
EtherealFDB003275
FruitFDB003275
FruityFDB003275
SweetFDB003275
TropicalFDB003275
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Acetyl-CoA + isobutanol → isobutyl acetate + Coenzyme A
isobutyl acetate + water → Acetic acid + isobutanol + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f217b5e6b92235a1dd71JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-25cc25b3ba0651c0ba45JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-47909851abe2172156c6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-32ed7cd25a7cd585255aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-497069f05d541433b66eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-49585f528507ace5b393JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-014i-1900000000-bb28c34b11812942773dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-ef6ece5c35a5dd154ad5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f217b5e6b92235a1dd71JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-25cc25b3ba0651c0ba45JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-47909851abe2172156c6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-32ed7cd25a7cd585255aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-497069f05d541433b66eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-49585f528507ace5b393JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-014i-1900000000-bb28c34b11812942773dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-ef6ece5c35a5dd154ad5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-df6cefc23abcd1e80417JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-9700000000-a748f357862b1b998434JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-edefa0d353dff24eb16bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-f40694d799cd17a2cec4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-7900000000-6534ebe4a3a380503d44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-9200000000-fd7dc8a883948134a340JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e0b525315cc093f0fd0cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-6eb8c377976b6fa47cd1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-75ca9d459a88c83adee2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4531d1e7d918cb3881e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0600-9200000000-9d3e1ac44fb825b68474JSpectraViewer
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-e19c8390ed8f55d45a2dJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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 ID50569
HMDB IDHMDB0031246
Pubchem Compound ID8038
Kegg IDNot Available
ChemSpider ID7747
FOODB IDFDB003275
WikipediaIsobutyl_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