Tmic
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Record Information
Version2.0
Creation Date2014-09-11 05:19:13 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4851
Identification
Common NameIsopentyl acetate
ClassSmall Molecule
DescriptionIsopentyl acetate is found in apple. Isopentyl acetate is present in many fruit aromas, especially banana. Isopentyl acetate is used in banana flavouring. Isoamyl acetate has a strong odor (similar to Juicy Fruit or a pear drop) which is also described as similar to both banana and pear. Banana oil is a term that is applied either to pure isoamyl acetate or to flavorings that are mixtures of isoamyl acetate, amyl acetate, nitrocellulose and other flavors. Pear oil commonly refers to a solution of isoamyl acetate in ethanol that is used as an artificial flavor. Isoamyl acetate, also known as isopentyl acetate, is an organic compound that is the ester formed from isoamyl alcohol and acetic acid. It is a clear colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isopentyl acetate belongs to the family of Carboxylic Acid Esters. These are carboxylic acid derivatives in which the carbo atom from the carbonyl group is atached to an alkyl or oaryl moiety through an oxygen atom (forming an ester group).
Compound Type
  • Ester
  • Ether
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Solvent
Chemical Structure
Thumb
Synonyms
Synonym
1-Butanol, 3-methyl-, 1-acetate
1-Butanol, 3-methyl-, acetate
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-Methylbutyl acetate
3-Methylbutyl ethanoate
FEMA 2055
Isoamyl acetate
Isoamyl ethanoate
Isopentyl acetic acid
Isopentyl ethanoate
Chemical FormulaC7H14O2
Average Molecular Mass130.185 g/mol
Monoisotopic Mass130.099 g/mol
CAS Registry Number123-92-2
IUPAC Name3-methylbutyl acetate
Traditional Namebanana oil
SMILESCC(C)CCOC(C)=O
InChI IdentifierInChI=1S/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3
InChI KeyInChIKey=MLFHJEHSLIIPHL-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-78.5 °C
Boiling PointNot Available
Solubility2 mg/mL at 25 °C
LogP2.25
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-b39e66ca9f24f516c159View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-25e59405f21ad74bf82dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-712ec54497a1b720e6f4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9000000000-8c50c23b8716d739a931View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9000000000-6eb9d62df8623ee92ac6View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-0900000000-21654613d581d7671bbcView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-fe72c0ec89d09374d63aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-b39e66ca9f24f516c159View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-25e59405f21ad74bf82dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-712ec54497a1b720e6f4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9000000000-8c50c23b8716d739a931View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9000000000-6eb9d62df8623ee92ac6View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-0900000000-21654613d581d7671bbcView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-fe72c0ec89d09374d63aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5cec3842741b72d2888bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-5900000000-38618594a20a626349f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-ed5c80c34661648c5359View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-8371bc765eaa9253dd3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-7900000000-d2baceb7d855f1c63083View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-a0d1c48d52d2bcc8e9e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-cfa80356b0c95bba654bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-07a7afc7d858b6cfbcbdView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31528
PubChem Compound ID31276
ChEMBL IDCHEMBL42013
ChemSpider ID29016
KEGG IDC12296
UniProt IDNot Available
OMIM ID
ChEBI ID31725
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkIsopentyl_acetate
References
Synthesis ReferenceNot Available
MSDST3D4851.pdf
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.92 uMNVS_NR_hPXRNovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.58 uMNVS_ADME_hCYP2C9Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]