Record Information
Version1.0
Created at2020-03-19 00:51:38 UTC
Updated at2020-12-07 19:07:41 UTC
CannabisDB IDCDB000695
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIsobutyl acetate
DescriptionAcetic acid-2-methyl-propyl ester or 2-methylpropyl acetate or 2-methylpropyl ethanoate, also known as isobutylacetate, 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). Isobutyl acetate is a clear, colorless liquid that is only slightly soluble in water (0.7 g/100 mL). Isobutyl acetate is produced from the esterification of isobutanol with acetic acid. Industrially, it is used as a solvent for lacquer and nitrocellulose. It is found naturally in many fruits such as raspberries and pears. Isobutyl aceteate has a sweet, apple, tropical, banana aroma and a similar fruity taste. At higher concentrations the odor can be unpleasant and may cause symptoms of central nervous system depression such as nausea, dizziness and headache. Isobutyl acetate has been detected, but not quantified in, several different fruits, such as muskmelons, sweet bay, asian pears, cocoa beans, figs, papaya and pineapple. This could make isobutyl acetate a potential biomarker for the consumption of these foods. Isobutyl acetate has also been found in Cannabis sativa (PMID: 6991645 , 26657499 ).
Structure
Thumb
Synonyms
ValueSource
2-Methyl-1-propyl acetateChEBI
2-Methylpropyl ethanoateChEBI
Acetate d'isobutyleChEBI
Acetic acid, 2-methylpropyl esterChEBI
Acetic acid, isobutyl esterChEBI
beta-Methylpropyl ethanoateChEBI
EssigsaeureisobutylesterChEBI
I-butyl acetateChEBI
Isobutyl ethanoateChEBI
IsobutylacetatChEBI
IsobutylazetatChEBI
2-Methyl-1-propyl acetic acidGenerator
2-Methylpropyl ethanoic acidGenerator
Acetic acid d'isobutyleGenerator
Acetate, 2-methylpropyl esterGenerator
Acetate, isobutyl esterGenerator
b-Methylpropyl ethanoateGenerator
b-Methylpropyl ethanoic acidGenerator
beta-Methylpropyl ethanoic acidGenerator
Β-methylpropyl ethanoateGenerator
Β-methylpropyl ethanoic acidGenerator
I-butyl acetic acidGenerator
Isobutyl ethanoic acidGenerator
2-Methylpropyl acetic acidGenerator
2-Methyl-1-propanol, acetateHMDB
2-Methylpropyl acetate, 9ciHMDB
beta -Methylpropyl ethanoateHMDB
FEMA 2175HMDB
Isobutyl acetateHMDB
Isobutyl acetate FCCHMDB
Isobutyl acetate, 8ciHMDB
Isobutylester kyseliny octoveHMDB
Isobutyl acetic acidGenerator
IsobutylacetateMeSH
Chemical FormulaC6H12O2
Average Molecular Weight116.16
Monoisotopic Molecular Weight116.0837
IUPAC Name2-methylpropyl acetate
Traditional Nameisobutyl acetate
CAS Registry Number110-19-0
SMILES
CC(C)COC(C)=O
InChI Identifier
InChI=1S/C6H12O2/c1-5(2)4-8-6(3)7/h5H,4H2,1-3H3
InChI KeyGJRQTCIYDGXPES-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

Industrial application:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-98.85 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.3 mg/mL at 25 °CNot Available
logP1.78Not Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-f217b5e6b92235a1dd71Spectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-25cc25b3ba0651c0ba45Spectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-47909851abe2172156c6Spectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-32ed7cd25a7cd585255aSpectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-497069f05d541433b66eSpectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-49585f528507ace5b393Spectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-014i-1900000000-bb28c34b11812942773dSpectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-ef6ece5c35a5dd154ad5Spectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-f217b5e6b92235a1dd71Spectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-25cc25b3ba0651c0ba45Spectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-47909851abe2172156c6Spectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-32ed7cd25a7cd585255aSpectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-497069f05d541433b66eSpectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-49585f528507ace5b393Spectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-014i-1900000000-bb28c34b11812942773dSpectrum
GC-MSIsobutyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-ef6ece5c35a5dd154ad5Spectrum
Predicted GC-MSIsobutyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-df6cefc23abcd1e80417Spectrum
Predicted GC-MSIsobutyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-9700000000-a748f357862b1b9984342016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-edefa0d353dff24eb16b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-f40694d799cd17a2cec42016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-7900000000-6534ebe4a3a380503d442016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-9200000000-fd7dc8a883948134a3402016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e0b525315cc093f0fd0c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-6eb8c377976b6fa47cd12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-75ca9d459a88c83adee22021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4531d1e7d918cb3881e52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0600-9200000000-9d3e1ac44fb825b684742021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e19c8390ed8f55d45a2d2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0031246
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003275
KNApSAcK IDC00050471
Chemspider ID7747
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsobutyl_acetate
METLIN IDNot Available
PubChem Compound8038
PDB IDNot Available
ChEBI ID50569
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 ]