Showing Compound Card for 1-Butanol-3-methyl acetate (CDB000696)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:51:41 UTC
Updated at2020-12-07 19:07:41 UTC
CannabisDB IDCDB000696
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1-Butanol-3-methyl acetate
Description1-Butanol-3-methyl acetate, isoamyl acetate or isopentyl acetate, 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). Isoamyl acetate is the 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. 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 is used in banana flavouring. Isoamyl acetate is found naturally in the banana plant. Isoamyl acetate has also been found in Cannabis sativa (PMID: 6991645 , 26657499 ). In addition to its role as a flavoring or aroma agent in foods and perfumes, isoamyl acetate is released by a honey bee's sting where it serves as a pheromone to attract other bees and provoke them to sting ( PMID: 13870346 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight130.18
Monoisotopic Molecular Weight130.0994
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

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-78.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2 mg/mL at 25 °CNot Available
logP2.25Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-07a7afc7d858b6cfbcbd2014-09-20View Spectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-00kf-9000000000-b39e66ca9f24f516c159Spectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-004i-9000000000-25e59405f21ad74bf82dSpectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-712ec54497a1b720e6f4Spectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-006x-9000000000-8c50c23b8716d739a931Spectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-00dl-9000000000-6eb9d62df8623ee92ac6Spectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-21654613d581d7671bbcSpectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-fe72c0ec89d09374d63aSpectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-00kf-9000000000-b39e66ca9f24f516c159Spectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-004i-9000000000-25e59405f21ad74bf82dSpectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-712ec54497a1b720e6f4Spectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-006x-9000000000-8c50c23b8716d739a931Spectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-00dl-9000000000-6eb9d62df8623ee92ac6Spectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-21654613d581d7671bbcSpectrum
GC-MS1-Butanol-3-methyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-fe72c0ec89d09374d63aSpectrum
Predicted GC-MS1-Butanol-3-methyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-5cec3842741b72d2888bSpectrum
Predicted GC-MS1-Butanol-3-methyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-5900000000-38618594a20a626349f22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-ed5c80c34661648c53592016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-8371bc765eaa9253dd3e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-7900000000-d2baceb7d855f1c630832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-a0d1c48d52d2bcc8e9e72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-cfa80356b0c95bba654b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-9000000000-94d22b8671a4b150f4da2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9000000000-8fdf0cfc29d75b55c9932021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1a376d8c519c265461102021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-9000000000-313bea5d0d6a31ec59652021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-57efb85ba2c5a7c82d4c2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0031528
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  3. BOCH R, SHEARER DA, STONE BC: Identification of isoamyl acetate as an active component in the sting pheromone of the honey bee. Nature. 1962 Sep 8;195:1018-20. doi: 10.1038/1951018b0. [PubMed:13870346 ]