Showing Compound Card for 2-Butanone (CDB000500)

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Record Information
Version1.0
Created at2020-03-19 00:40:24 UTC
Updated at2020-12-07 19:07:28 UTC
CannabisDB IDCDB000500
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Butanone
Description2-Butanone or Butanone, also known as methylethylketone or MEK, belongs to the class of organic compounds known as ketones. It is an organic compound with the formula CH3C(O)CH2CH3. Ketones are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, butanone is considered to be an oxygenated hydrocarbon lipid molecule. Butanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It has been isolated from hop oil (Humulus lupulus), white clover (Trifolium repens), tea, tomatoes, various fruits and other vegetable sources. It is used in the refining and extraction of fats and oils. Butanone is an irritant, but serious health effects in animals have been seen only at very high levels. When inhaled, these effects included birth defects. Butanone occurs as a natural product. It is produced by some trees and found in some fruits and vegetables in small amounts. It is also released to the air from car and truck exhausts. The known health effects to people from exposure to butanone are irritation of the nose, throat, skin, and eyes. This colorless liquid has a sharp, sweet odor, reminiscent of butterscotch and acetone. It is produced industrially at a large scale, and also occurs in trace amounts in nature. Butanol can also be found in the volatile fraction of Cannabis sativa (PMID: 26657499 ) and is likely a component of marijuana smoke ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-ButanonChEBI
2-ButanoneChEBI
3-ButanoneChEBI
AethylmethylketonChEBI
Butanone 2ChEBI
C2H5COCH3ChEBI
Ethyl methyl cetoneChEBI
Ethyl methyl ketoneChEBI
Ethyl(methyl) ketoneChEBI
Ethylmethyl ketoneChEBI
EthylmethylketonChEBI
MeetcoChEBI
MEKChEBI
Methyl acetoneChEBI
Methyl ethyl cetoneChEBI
Methyl ethyl ketoneChEBI
Methyl(ethyl) ketoneChEBI
MethylacetoneChEBI
Methylethyl ketoneChEBI
MethylethylketonChEBI
OxobutaneChEBI
Butan-2-oneKegg
ButanoneChEBI
Chemical FormulaC4H8O
Average Molecular Weight72.11
Monoisotopic Molecular Weight72.0575
IUPAC Namebutan-2-one
Traditional Namemethyl(ethyl) ketone
CAS Registry Number78-93-3
SMILES
CCC(C)=O
InChI Identifier
InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
InChI KeyZWEHNKRNPOVVGH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-86.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility223 mg/mLNot Available
logP0.29HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP0.41ALOGPS
logP0.81ChemAxon
logS0.11ALOGPS
pKa (Strongest Acidic)19.68ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.82 m³·mol⁻¹ChemAxon
Polarizability8.28 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)splash10-0006-9000000000-389580382a5be690811f2014-09-20View Spectrum
GC-MS2-Butanone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-6d2b5f585a1d1bc5a8fbSpectrum
GC-MS2-Butanone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-9d38ccb9b91100a7ec9aSpectrum
GC-MS2-Butanone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-c956d364a703ad576f74Spectrum
GC-MS2-Butanone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-6d2b5f585a1d1bc5a8fbSpectrum
GC-MS2-Butanone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-9d38ccb9b91100a7ec9aSpectrum
GC-MS2-Butanone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-c956d364a703ad576f74Spectrum
Predicted GC-MS2-Butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-4e6c1888a6b9f92a7e0cSpectrum
Predicted GC-MS2-Butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-9000000000-ce6384a82cdbc3c321312012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05fr-9000000000-d2220466d540748715a62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-5c396f6150d62df63bf82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-342b15824555f25c17ae2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-9d38ccb9b91100a7ec9a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-9000000000-c956d364a703ad576f742012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-9000000000-df1c4f4393ad8e083cee2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-5db9dc68e554d23fe4ca2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e76aaa16e1218b6b92e02015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-9000000000-df1c4f4393ad8e083cee2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-5db9dc68e554d23fe4ca2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e76aaa16e1218b6b92e02015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-75ee4bf0cca979df2fee2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-a0882d603db69a60cd2b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9000000000-2b71687b4480da0a40a82015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-75ee4bf0cca979df2fee2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-a0882d603db69a60cd2b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9000000000-2b71687b4480da0a40a82015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-1924391f943e092b44862021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-b1f7b08e06d7bb20906d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-9000000000-d0609c2afd15f75e6cbb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-77e5dcf17bd83eca2c672021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9000000000-91a2cd469019aa3b0b9c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-fa8f185babb9571dbb912021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000474
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003383
KNApSAcK IDC00054019
Chemspider ID6321
KEGG Compound IDC02845
BioCyc IDMEK
BiGG IDNot Available
Wikipedia LinkButanone
METLIN ID5461
PubChem Compound6569
PDB IDNot Available
ChEBI ID28398
References
General References
  1. 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 ]