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Acetone (FDB008301)

Record Information
Version1.0
Creation date2010-04-08 22:08:01 UTC
Update date2020-09-17 15:36:00 UTC
Primary IDFDB008301
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetone
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 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
CAS Number67-64-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility193 g/LALOGPS
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
Chemical FormulaC3H6O
IUPAC namepropan-2-one
InChI IdentifierInChI=1S/C3H6O/c1-3(2)4/h1-2H3
InChI KeyCSCPPACGZOOCGX-UHFFFAOYSA-N
Isomeric SMILESCC(C)=O
Average Molecular Weight58.0791
Monoisotopic Molecular Weight58.041864814
Classification
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:

Process

Industrial process:

Naturally occurring process:

Role

Biological role:

Environmental role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 62.04%; H 10.41%; O 27.55%DFC
Melting PointMp -94°DFC
Boiling PointBp 56.2°DFC
Experimental Water Solubility1000 mg/mL at 25 oCRIDDICK,JA et al. (1986)
Experimental logP-0.24HANSCH,C ET AL. (1995)
Experimental pKa20
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd2525 0.79DFC
Refractive Indexn20D 1.3588DFC
Spectra
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
ChemSpider ID175
ChEMBL IDCHEMBL14253
KEGG Compound IDC00207
Pubchem Compound ID180
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01659
CRC / DFC (Dictionary of Food Compounds) IDDFS24-J:DFS24-J
EAFUS ID24
Dr. Duke IDACETONE
BIGG ID34257
KNApSAcK IDNot Available
HET IDACN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1001331
SuperScent ID180
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
narcotic35482 A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.DUKE
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Ketone Body MetabolismSMP00071 map00072
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
apple
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
solvent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ethereal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pear
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).