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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:43:52 UTC
Update Date2022-03-07 02:53:01 UTC
HMDB IDHMDB0031528
Secondary Accession Numbers
  • HMDB31528
Metabolite Identification
Common NameIsopentyl acetate
DescriptionIsopentyl acetate, also known as isoamyl acetate 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 ester formed from isoamyl alcohol and acetic acid. It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isopentyl acetate has a sweet, fruity banana odor and similar sweet, fruity banana taste. Isopentyl acetate is used to confer banana flavor in foods. Isopentyl acetate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Outside of the human body, Isopentyl acetate is found, on average, in the highest concentration within a few different foods, such as red wines, white wines, and beers. Isopentyl acetate has also been detected, but not quantified in, several different foods, such as blackberries (Rubus), figs (Ficus carica), red teas, bananas (Musa acuminata), and black elderberries (Sambucus nigra). This could make isopentyl acetate a potential biomarker for the consumption of these foods. Isopentyl acetate occurs naturally in the banana plant and it is also produced synthetically. Based on a literature review a significant number of articles have been published on Isopentyl acetate. Pure isopentyl acetate, or mixtures of isopentyl acetate, amyl acetate, and other flavors may be referred to as banana oil. Because of its intense, pleasant odor and its low toxicity, isopentyl acetate is used to test the effectiveness of respirators or gas masks. Isopentyl acetate is released by a honey bee's sting where it serves as a pheromone beacon to attract other bees and provoke them to sting.
Structure
Data?1563862137
Synonyms
ValueSource
3-Methyl-1-butanol acetateChEBI
3-Methyl-1-butyl acetateChEBI
3-Methyl-but-1-yl acetateChEBI
3-Methylbutyl acetateChEBI
3-Methylbutyl ethanoateChEBI
Acetate d'isoamyleChEBI
Acetate d'isopentyleChEBI
Acetate de 3-methylbutyleChEBI
Acetic acid, 3-methylbutyl esterChEBI
Acetic acid, isopentyl esterChEBI
Amylacetic esterChEBI
beta-Methyl butyl acetateChEBI
CH3C(O)O(CH2)2ch(CH3)2ChEBI
I-amyl acetateChEBI
Isoamyl ethanoateChEBI
IsoamylacetatChEBI
IsoamylazetatChEBI
Isopentyl ethanoateChEBI
3-Methyl-1-butanol acetic acidGenerator
3-Methyl-1-butyl acetic acidGenerator
3-Methyl-but-1-yl acetic acidGenerator
3-Methylbutyl acetic acidGenerator
3-Methylbutyl ethanoic acidGenerator
Acetic acid d'isoamyleGenerator
Acetic acid d'isopentyleGenerator
Acetic acid de 3-methylbutyleGenerator
Acetate, 3-methylbutyl esterGenerator
Acetate, isopentyl esterGenerator
b-Methyl butyl acetateGenerator
b-Methyl butyl acetic acidGenerator
beta-Methyl butyl acetic acidGenerator
Β-methyl butyl acetateGenerator
Β-methyl butyl acetic acidGenerator
I-amyl acetic acidGenerator
Isoamyl ethanoic acidGenerator
Isopentyl ethanoic acidGenerator
Isopentyl acetic acidGenerator
IsopentylacetateMeSH
1-Butanol, 3-methyl-, 1-acetateHMDB
1-Butanol, 3-methyl-, acetateHMDB
3-Methyl butyl ester acetic acidHMDB
3-Methyl-1-butanol, acetateHMDB
3-Methyl-1-butanyl acetateHMDB
FEMA 2055HMDB
Isoamyl acetateHMDB
Isopentyl acetateChEBI
Isoamyl acetic acidGenerator
Chemical FormulaC7H14O2
Average Molecular Weight130.1849
Monoisotopic Molecular Weight130.099379692
IUPAC Name3-methylbutyl acetate
Traditional Namebanana oil
CAS Registry Number123-92-2
SMILES
CC(C)CCOC(C)=O
InChI Identifier
InChI=1S/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3
InChI KeyMLFHJEHSLIIPHL-UHFFFAOYSA-N
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
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-78.5 °CNot Available
Boiling Point142.00 to 143.00 °C. @ 756.00 mm HgThe Good Scents Company Information System
Water Solubility2 mg/mL at 25 °CNot Available
LogP2.25Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.63531661259
DarkChem[M-H]-124.76831661259
DeepCCS[M+H]+133.54930932474
DeepCCS[M-H]-131.34230932474
DeepCCS[M-2H]-167.45230932474
DeepCCS[M+Na]+142.30630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isopentyl acetateCC(C)CCOC(C)=O1163.0Standard polar33892256
Isopentyl acetateCC(C)CCOC(C)=O858.6Standard non polar33892256
Isopentyl acetateCC(C)CCOC(C)=O894.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-00kf-9000000000-b39e66ca9f24f516c1592017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-004i-9000000000-25e59405f21ad74bf82d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-0006-9000000000-712ec54497a1b720e6f42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-006x-9000000000-8c50c23b8716d739a9312017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-00dl-9000000000-6eb9d62df8623ee92ac62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate CI-B (Non-derivatized)splash10-001i-0900000000-21654613d581d7671bbc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-0006-9000000000-fe72c0ec89d09374d63a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-00kf-9000000000-b39e66ca9f24f516c1592018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-004i-9000000000-25e59405f21ad74bf82d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-0006-9000000000-712ec54497a1b720e6f42018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-006x-9000000000-8c50c23b8716d739a9312018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-00dl-9000000000-6eb9d62df8623ee92ac62018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate CI-B (Non-derivatized)splash10-001i-0900000000-21654613d581d7671bbc2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)splash10-0006-9000000000-fe72c0ec89d09374d63a2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopentyl acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5cec3842741b72d2888b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopentyl acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-07a7afc7d858b6cfbcbd2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 10V, Positive-QTOFsplash10-001i-5900000000-38618594a20a626349f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 20V, Positive-QTOFsplash10-00di-9100000000-ed5c80c34661648c53592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 40V, Positive-QTOFsplash10-0abc-9000000000-8371bc765eaa9253dd3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 10V, Negative-QTOFsplash10-004i-7900000000-d2baceb7d855f1c630832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 20V, Negative-QTOFsplash10-0a4i-9200000000-a0d1c48d52d2bcc8e9e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 40V, Negative-QTOFsplash10-0a4l-9000000000-cfa80356b0c95bba654b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 10V, Positive-QTOFsplash10-00dl-9000000000-94d22b8671a4b150f4da2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 20V, Positive-QTOFsplash10-05fr-9000000000-8fdf0cfc29d75b55c9932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 40V, Positive-QTOFsplash10-0006-9000000000-1a376d8c519c265461102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 10V, Negative-QTOFsplash10-052r-9000000000-313bea5d0d6a31ec59652021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 20V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopentyl acetate 40V, Negative-QTOFsplash10-0a4i-9000000000-57efb85ba2c5a7c82d4c2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008132
KNApSAcK IDC00035116
Chemspider ID29016
KEGG Compound IDC12296
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsoamyl acetate
METLIN IDNot Available
PubChem Compound31276
PDB IDNot Available
ChEBI ID31725
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006711
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .