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Identification
YMDB IDYMDB00571
Nameisoamyl acetate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionIsopentyl acetate, also known as acetate d'isoamyle or amylacetic 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). Isopentyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Isopentyl acetate is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1-Butanol, 3-methyl-, acetate
  • 2-Methylbutyl ethanoate
  • 3-Methyl butyl ester acetic acid
  • 3-Methyl-1-butanol acetate
  • 3-Methyl-1-butanol, acetate
  • 3-Methyl-1-butanyl acetate
  • 3-Methyl-1-butyl acetate
  • 3-methyl-1-butyl acetate (isoamyl acetate)
  • 3-methyl-but-1-yl acetate
  • 3-Methylbutyl acetate
  • 3-Methylbutyl ester of acetic acid
  • 3-Methylbutyl ethanoate
  • acetate d'isoamyle
  • acetate d'isopentyle
  • acetate de 3-methylbutyle
  • ACETATE ION
  • Acetic acid, 3-methylbutyl ester
  • acetic acid, ion(1-)
  • Acetic acid, isoamyl ester
  • Acetic acid, isopentyl ester
  • Amyl acetate ester
  • Amyl acetate, common
  • amylacetic ester
  • Azetat
  • Banana oil
  • beta-Methyl butyl acetate
  • Ethanoat
  • ethanoate
  • i-Amyl acetate
  • Isoamyl acetate
  • Isoamyl acetate
  • Isoamyl ethanoate
  • Isoamylacetat
  • Isoamylazetat
  • Isoamylester kyseliny octove
  • Isopentyl acetate
  • Isopentyl alcohol, acetate
  • Isopentyl alcohol, acetate pear oil
  • Isopentyl ester acetic acid
  • Isopentyl ethanoate
  • Jargonelle pear essence
  • MeCO2 anion
  • Pear oil
  • CH3C(O)O(CH2)2ch(CH3)2
  • 3-Methyl-1-butanol acetic acid
  • 3-Methyl-1-butyl acetic acid
  • 3-Methyl-but-1-yl acetic acid
  • 3-Methylbutyl ethanoic acid
  • Acetic acid d'isoamyle
  • Acetic acid d'isopentyle
  • Acetic acid de 3-methylbutyle
  • Acetate, 3-methylbutyl ester
  • Acetate, isopentyl ester
  • b-Methyl butyl acetate
  • b-Methyl butyl acetic acid
  • beta-Methyl butyl acetic acid
  • Β-methyl butyl acetate
  • Β-methyl butyl acetic acid
  • I-amyl acetic acid
  • Isoamyl ethanoic acid
  • Isopentyl ethanoic acid
  • Isopentyl acetic acid
  • 1-Butanol, 3-methyl-, 1-acetate
  • FEMA 2055
  • Isopentylacetate
  • Isoamyl acetic acid
CAS number123-92-2
WeightAverage: 130.1849
Monoisotopic: 130.099379692
InChI KeyMLFHJEHSLIIPHL-UHFFFAOYSA-N
InChIInChI=1S/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3
IUPAC Name3-methylbutyl acetate
Traditional IUPAC Namebanana oil
Chemical FormulaC7H14O2
SMILESCC(C)CCOC(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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateLiquid
Charge0
Melting point-78.5 °C
Experimental Properties
PropertyValueReference
Water Solubility2 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP2.25 [DAYLIGHT (2003)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.06 g/LALOGPS
logP2.36ALOGPS
logP1.53ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.84 m³·mol⁻¹ChemAxon
Polarizability15.18 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • endoplasmic reticulum
  • nucleus
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
BananaFDB008132
BitterFDB008132
FruityFDB008132
SolventFDB008132
SweetFDB008132
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Acetyl-CoA + isoamylolisoamyl acetate + Coenzyme A
isoamyl acetate + waterAcetic acid + isoamylol + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Ma, J., Lu, Q., Yuan, Y., Ge, H., Li, K., Zhao, W., Gao, Y., Niu, L., Teng, M. (2011). "Crystal structure of isoamyl acetate-hydrolyzing esterase from Saccharomyces cerevisiae reveals a novel active site architecture and the basis of substrate specificity." Proteins 79:662-668.21069734
  • Erten, H., Tanguler, H. (2010). "Influence of Williopsis saturnus yeasts in combination with Saccharomyces cerevisiae on wine fermentation." Lett Appl Microbiol 50:474-479.20214731
  • Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
  • 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
  • Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID31725
HMDB IDHMDB0031528
Pubchem Compound ID31276
Kegg IDC12296
ChemSpider ID29016
FOODB IDFDB008132
WikipediaIsoamyl_acetate
BioCyc IDNot Available

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Displays enzymatic activity both for medium-chain fatty acid (MCFA) ethyl ester synthesis and hydrolysis (esterase activity). MCFA are toxic for yeast and this enzyme could thus be involved in their detoxification by esterification
Gene Name:
EHT1
Uniprot ID:
P38295
Molecular weight:
51254.80078
Reactions
Acetyl-CoA + an alcohol → CoA + an acetyl ester.
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 carboxylesterase activity
Specific function:
Displays enzymatic activity both for medium-chain fatty acid (MCFA) ethyl ester synthesis and hydrolysis (esterase activity). MCFA are toxic for yeast and this enzyme could thus be involved in their detoxification by esterification
Gene Name:
EEB1
Uniprot ID:
Q02891
Molecular weight:
51723.19922
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.
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