Record Information
Version1.0
Creation date2010-04-08 22:08:01 UTC
Update date2015-10-09 22:31:03 UTC
Primary IDFDB008301
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetone
DescriptionSolvent used in food processing as a colour diluent, flavour ingredient, etc. Acetone evaporates rapidly, even from water and soil. Once in the atmosphere, it is degraded by UV light with a 22-day half-life. Acetone dissipates slowly in soil, animals, or waterways since it is sometimes consumed by microorganisms; however, it is a significant issue with respect to groundwater contamination due to its high solubility in water. The LD50 of acetone for fish is 8.3 g/l of water (or about 0.8%) over 96 hours, and its environmental half-life is about 1 to 10 days. Acetone may pose a significant risk of oxygen depletion in aquatic systems due to the microbial activity consuming it.; Acetone is a good solvent for most plastics and synthetic fibres including those used in Nalgene bottles made of polystyrene, polycarbonate and some types of polypropylene.. It is ideal for thinning fiberglass resin, cleaning fiberglass tools and dissolving two-part epoxies and superglue before hardening. It is used as a volatile component of some paints and varnishes. As a heavy-duty degreaser, it is useful in the preparation of metal prior to painting; it also thins polyester resins, vinyl and adhesives.; Acetone is often the primary component in cleaning agents such as nail polish remover. Ethyl acetate, another organic solvent, is sometimes used as well. Acetone is a component of superglue remover and it easily removes residues from glass and porcelain.; Acetone is one of the ketone bodies produced during ketoacidosis. Acetone is not regarded as a waste product of metabolism. However, its physiological role in biochemical machinery is not clear. A model for the role of acetone metabolism is presented that orders the events occurring in acetonemia in sequence: in diabetic ketosis or starvation, ketone body production (b-hydroxy-butyrate, acetoacetate) provides fuel for vital organs (heart, brain . . .) raising the chance of survival of the metabolic catastrophe. However, when ketone body production exceeds the degrading capacity, the accumulating acetoacetic acid presents a new challenge to the pH regulatory system. Acetone production and its further degradation to C3 fragments fulfill two purposes: the maintenance of pH buffering capacity and provision of fuel for peripheral tissues. Since ketosis develops under serious metabolic circumstances, all the mechanisms that balance or moderate the effects of ketosis enhance the chance for survival. From this point of view, the theory that transportable C3 fragments can serve as additional nutrients is a novel view of acetone metabolism which introduces a new approach to the study of acetone degradation, especially in understanding its physiological function and the interrelationship between liver and peripheral tissues. (PMID 10580530). Acetone is typically derived from acetoacetate through the action of microbial acetoacetate decarboxylases found in gut microflora.; In chemistry, acetone is the simplest representative of the ketones. Acetone is a colorless, mobile, flammable liquid readily soluble in water, ethanol, ether, etc., and itself serves as an important solvent. ; Acetone is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage).; Acetone is the organic compound with the formula OC(CH3)2. This colorless, mobile, flammable liquid is the simplest example of the ketones. Owing to the fact that acetone is miscible with water, and virtually all organic solvents, it serves as an important solvent in its own right, typically the solvent of choice for cleaning purposes in the laboratory. More than 3 billion kilograms are produced annually, mainly as a precursor to polymers. Familiar household uses of acetone are as the active ingredient in nail polish remover and as paint thinner and sanitary cleaner/ nail polish remover base. It is a common building block in organic chemistry. In addition to being manufactured, acetone also occurs naturally, even being biosynthesized in small amounts in the human body.; Bisphenol-A is a component of many polymers such as polycarbonates, polyurethanes, and epoxy resins.; In the laboratory, acetone is used as a polar aprotic solvent in a variety of organic reactions, such as SN2 reactions. The use of acetone solvent is also critical for the Jones oxidation. It is a common solvent for rinsing laboratory glassware because of its low cost, volatility, and ability to dissolve water. For similar reasons, acetone is also used as a drying agent. Acetone can be cooled with dry ice to -78 °C without freezing; acetone/dry ice baths are commonly used to conduct reactions at low temperatures. Acetone is fluorescent under ultraviolet light, and acetone vapor may be used as a fluorescent tracer in fluid flow experiments.; When oxidized, acetone forms acetone peroxide as a byproduct, which is a highly unstable compound. It may be formed accidentally, e.g. when waste hydrogen peroxide is poured into waste solvent containing acetone. Acetone peroxide is more than ten times as friction and shock sensitive as nitroglycerin. Due to its instability, it is rarely used, despite its easy chemical synthesis.
CAS Number67-64-1
Structure
Thumb
Synonyms
SynonymSource
(CH3)2CObiospider
β-ketopropanebiospider
2-PropanoneChEBI
2-Propanone, 9CIdb_source
AcetonChEBI
Acetone oilbiospider
Acetonumbiospider
AzetonChEBI
b-KetopropaneGenerator
beta-KetopropaneChEBI
Dimethyl ketonedb_source
DimethylcetoneChEBI
DimethylformaldehydeHMDB
DimethylketonChEBI
DimethylketoneChEBI
FEMA 3326db_source
Methyl ketoneChEBI
PropanonChEBI
PropanoneChEBI
Pyroacetic etherChEBI
Sasetonebiospider
β-ketopropaneGenerator
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC3H6O
IUPAC namepropan-2-one
InChI IdentifierInChI=1S/C3H6O/c1-3(2)4/h1-2H3
InChI KeyInChIKey=CSCPPACGZOOCGX-UHFFFAOYSA-N
Isomeric SMILESCC(C)=O
Average Molecular Weight58
Monoisotopic Molecular Weight58
Classification
ClassificationNot classified
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-14f33068e4ba092deb77View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-23fa1a3953b34b4d17dbView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-5de48058c986d7c07ac3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-ac4e03d64a5d08cb0e2dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-bc353e3a40f83275872bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9000000000-cbc26702df42f89389a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052f-9000000000-76023af14a12c4b19cf9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-9000000000-4a0900faf782fa344db9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-052f-9000000000-cd6003561b339cd9243fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-23fa1a3953b34b4d17dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-5de48058c986d7c07ac3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-31f47c962fee2ab51810View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-29f0bd4f29c752b098b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-44feb4a0693788e21f10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-e3c53a345dc69a6403f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-786aa0674415a8c32182View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-3bc848ca563aa39df37eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-e24ae6a1f2f0e7aac3e7View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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).