Showing Compound Card for 2-Propanone (CDB000698)

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Record Information
Version1.0
Created at2020-03-19 00:51:46 UTC
Updated at2020-12-07 19:07:42 UTC
CannabisDB IDCDB000698
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Propanone
DescriptionAcetone or 2-propanone, also known as dimethyl ketone, 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. Acetone is neutral molecule that is miscible in water. It readily dissolves in other organic solvents such as ethanol, methanol and diethyl ether. It occurs naturally in plants, trees, volcanic gases, forest fires, and is present in vehicle exhaust, alcoholic beverages, tobacco smoke, and landfill sites. Within the body small amounts of acetone are produced by the decarboxylation of ketone bodies (acetoacetate, beta-hydroxybutyrate). Certain dietary patterns, including prolonged fasting and high-fat low-carbohydrate dieting, can produce ketosis, in which acetone is formed in body tissue. More specifically, acetone can be produced from the oxidation of ingested isopropanol, or from the spontaneous/enzymatic breakdown of acetoacetate (a ketone body) in ketotic individuals. In humans acetone can be metabolized either by CYP2E1 via methylglyoxal to D-lactate and pyruvate (PMID 4285478 ). In addition to its presence in humans, acetone is found in a variety of foods and plants. Acetone has been rated as a generally recognized as safe (GRAS) substance when present in beverages, baked foods, desserts, and preserves at concentrations ranging from 5 to 8 mg/L. It is used as a flavor enhancer for sweetners in pickling mixes. Acetone is one of several ketones that are found in Cannabis sativa (PMID: 6991645 ). Acetone is widely used as an organic solvent and is the active ingredient in nail polish remover and as paint thinner. Acetone has been studied extensively and is believed to exhibit only slight toxicity in normal use. There is no strong evidence of chronic health effects if basic precautions are followed
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-PropanoneChEBI
AcetonChEBI
AzetonChEBI
beta-KetopropaneChEBI
Dimethyl ketoneChEBI
DimethylcetoneChEBI
DimethylketonChEBI
DimethylketoneChEBI
Methyl ketoneChEBI
PropanonChEBI
PropanoneChEBI
Pyroacetic etherChEBI
b-KetopropaneGenerator
Β-ketopropaneGenerator
DimethylformaldehydeHMDB
Chemical FormulaC3H6O
Average Molecular Weight58.08
Monoisotopic Molecular Weight58.0419
IUPAC Namepropan-2-one
Traditional Nameacetone
CAS Registry Number67-64-1
SMILES
CC(C)=O
InChI Identifier
InChI=1S/C3H6O/c1-3(2)4/h1-2H3
InChI KeyCSCPPACGZOOCGX-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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-94.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 25 °CNot Available
logP-0.24HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.29ALOGPS
logP0.11ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)19.51ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.19 m³·mol⁻¹ChemAxon
Polarizability6.41 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-e24ae6a1f2f0e7aac3e72014-09-20View Spectrum
GC-MSAcetone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-14f33068e4ba092deb77Spectrum
GC-MSAcetone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-23fa1a3953b34b4d17dbSpectrum
GC-MSAcetone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-5de48058c986d7c07ac3Spectrum
GC-MSAcetone, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-ac4e03d64a5d08cb0e2dSpectrum
GC-MSAcetone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-14f33068e4ba092deb77Spectrum
GC-MSAcetone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-23fa1a3953b34b4d17dbSpectrum
GC-MSAcetone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-5de48058c986d7c07ac3Spectrum
GC-MSAcetone, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-ac4e03d64a5d08cb0e2dSpectrum
Predicted GC-MSAcetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9000000000-bc353e3a40f83275872bSpectrum
Predicted GC-MSAcetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9000000000-cbc26702df42f89389a42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052f-9000000000-76023af14a12c4b19cf92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-9000000000-4a0900faf782fa344db92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-052f-9000000000-cd6003561b339cd9243f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-23fa1a3953b34b4d17db2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-5de48058c986d7c07ac32012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-31f47c962fee2ab518102015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-29f0bd4f29c752b098b12015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-44feb4a0693788e21f102015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-e3c53a345dc69a6403f22015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-786aa0674415a8c321822015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-3bc848ca563aa39df37e2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-6e3379842f4da69e8e2b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-6e3379842f4da69e8e2b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-9251850c7854d63a048f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-7d56b578e5d5ea65f9012021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-f1d310daeae27abc76722021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3f1c663ba1bd7d0121722021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)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 IDHMDB0001659
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008301
KNApSAcK IDC00048304
Chemspider ID175
KEGG Compound IDC00207
BioCyc IDACETONE
BiGG ID34257
Wikipedia LinkAcetone
METLIN ID3745
PubChem Compound180
PDB IDNot Available
ChEBI ID15347
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. Miller ON, Bazzano G: Propanediol metabolism and its relation to lactic acid metabolism. Ann N Y Acad Sci. 1965 Jul 31;119(3):957-73. doi: 10.1111/j.1749-6632.1965.tb47455.x. [PubMed:4285478 ]
  3. Kalapos MP: Possible physiological roles of acetone metabolism in humans. Med Hypotheses. 1999 Sep;53(3):236-42. doi: 10.1054/mehy.1998.0752. [PubMed:10580530 ]
  4. Abou-Zeid AA, Fouad M, Yassein M: Microbiological production of acetone-butanol by Clostridium acetobutylicum. Zentralbl Bakteriol Naturwiss. 1978;133(2):125-34. doi: 10.1016/s0323-6056(78)80023-8. [PubMed:685531 ]