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Record Information
Version3.6
Creation Date2005-11-20 22:13:15 UTC
Update Date2016-02-11 01:04:58 UTC
HMDB IDHMDB01659
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetone
DescriptionAcetone 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).
Structure
Thumb
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 Weight58.0791
Monoisotopic Molecular Weight58.041864814
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 KeyInChIKey=CSCPPACGZOOCGX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassKetones
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
StateLiquid
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
Water Solubility193.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.19 m3·mol-1ChemAxon
Polarizability6.41 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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 Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Gland
  • Bladder
  • Brain
  • Fibroblasts
  • Kidney
  • Liver
  • Myelin
  • Pancreas
  • Placenta
  • Skin
  • Stratum Corneum
  • Testes
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Ketone Body MetabolismSMP00071map00072
Succinyl CoA: 3-ketoacid CoA transferase deficiencySMP00569Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified47.3 (40.4 - 54.2) uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified30.0 +/- 20.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified106.0 (35.0-170.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified50.0 +/- 5.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1270.0 +/- 520.0 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified54.4 +/- 29.6 uMAdult (>18 years old)BothNormal details
Breast MilkDetected and Quantified10.3 +/- 6.4 uMAdult (>18 years old)Female
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified20 +/- 21 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified67.1 (43.0-91.2) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified117.0 +/- 65.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0 - 58.74 ppmChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNewborn (0-30 days old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified2-347 uMAdult (>18 years old)Male
normal
details
SalivaDetected and Quantified1-41 uMAdult (>18 years old)Male
normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified25.34 +/- 22.82 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified17 (1-198) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified17 (1-214) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified10 (<1-45) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified7 (<1-44) uMAdult (>18 years old)Female
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.24 +/- 4.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified5.2 umol/mmol creatinineNot SpecifiedMaleNormal details
UrineDetected and Quantified17.23-86.14 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified0.92 (0.20-2.8) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified3.914 +/- 3.929 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified4.2 (0.98-15.3) umol/mmol creatinineInfant (0-1 year old)BothNormal
    • Geigy Scientific ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified<6.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.9 (0.8-17.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified13.2 +/- 5.5 uMAdult (>18 years old)BothHeart Transplant details
BloodDetected and Quantified1520.0 (206.6-5285.0) uMAdult (>18 years old)BothAlcohol intoxication details
BloodDetected and Quantified25.0 +/- 85.0 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Pancreatic
details
Cerebrospinal Fluid (CSF)Detected and Quantified2700 uMAdult (>18 years old)Not SpecifiedHepatic encephalopathy details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected and Quantified0 - 32.93 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
UrineDetected and Quantified6.931 +/- 9.374 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified5.0 +/- 5.0 umol/mmol creatinineAdult (>18 years old)BothLung cancer details
UrineDetected and Quantified11.2 umol/mmol creatinineAdult (>18 years old)BothParaquat poisoning details
UrineDetected and Quantified13.2 umol/mmol creatinineAdult (>18 years old)BothDiabetes details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. [2779169 ]
Diabetes mellitus type 2
  1. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [6321058 ]
Hepatic encephalopathy
  1. Goldberg EM, Blendis LM, Sandler S: A gas chromatographic--mass spectrometric study of profiles of volatile metabolites in hepatic encephalopathy. J Chromatogr. 1981 Dec 11;226(2):291-9. [7320160 ]
Kidney disease
  1. Liebich HM, Woll J: Volatile substances in blood serum: profile analysis and quantitative determination. J Chromatogr. 1977 Nov 11;142:505-16. [914932 ]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [18953024 ]
Paraquat poisoning
  1. Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [9625050 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008301
KNApSAcK IDNot Available
Chemspider ID175
KEGG Compound IDC00207
BioCyc IDNot Available
BiGG ID34257
Wikipedia LinkAcetone
NuGOwiki LinkHMDB01659
Metagene LinkHMDB01659
METLIN ID3745
PubChem Compound180
PDB IDACN
ChEBI ID15347
References
Synthesis ReferenceIshizaki, Fumiaki. Acetone and butanol fermentation. Baiomasu Handobukku (2002), 166-175.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Robinson RC, Shorr RG, Varrichio A, Park SS, Gelboin HV, Miller H, Friedman FK: Human liver cytochrome P-450 related to a rat acetone-inducible, nitrosamine-metabolizing cytochrome P-450: identification and isolation. Pharmacology. 1989;39(3):137-44. [2587619 ]
  2. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. [15627241 ]
  3. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [6321058 ]
  4. Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [9625050 ]
  5. Wittmann S, Gilg T, Dietz HG, Grantzow R, Peschel O, von Meyer L: [Isopropanol and acetone level in serum after preoperative surface disinfection with antiseptics containing isopropanol] Blutalkohol. 1992 Sep;29(5):326-35. [1389018 ]
  6. Yamane N, Tsuda T, Nose K, Yamamoto A, Ishiguro H, Kondo T: Relationship between skin acetone and blood beta-hydroxybutyrate concentrations in diabetes. Clin Chim Acta. 2006 Mar;365(1-2):325-9. Epub 2005 Oct 11. [16223475 ]
  7. Palamanda J, Feng WW, Lin CC, Nomeir AA: Stimulation of tolbutamide hydroxylation by acetone and acetonitrile in human liver microsomes and in a cytochrome P-450 2C9-reconstituted system. Drug Metab Dispos. 2000 Jan;28(1):38-43. [10611138 ]
  8. Crawley SC, Hindsgaul O, Alton G, Pierce M, Palcic MM: An enzyme-linked immunosorbent assay for N-acetylglucosaminyltransferase-V. Anal Biochem. 1990 Feb 15;185(1):112-7. [2160776 ]
  9. Inoue S, Sato Y, Hasegawa H, Noguchi A, Yamada A, Kurata T, Iwasaki T: Cross-reactive antigenicity of nucleoproteins of lyssaviruses recognized by a monospecific antirabies virus nucleoprotein antiserum on paraffin sections of formalin-fixed tissues. Pathol Int. 2003 Aug;53(8):525-33. [12895231 ]
  10. Meiser JB, Nelson HS: Comparing conventional and acetone-precipitated dog allergen extract skin testing. J Allergy Clin Immunol. 2001 Apr;107(4):744-5. [11295672 ]
  11. Baum HP, Reichrath J, Theobald A, Schock G: Fixation requirements for the immunohistochemical reactivity of PCNA antibody PC10 on cryostat sections. Histochem J. 1994 Dec;26(12):929-33. [7896568 ]
  12. Benz J: Antidiabetic agents and lactation. J Hum Lact. 1992 Mar;8(1):27-8. [1558654 ]
  13. Benfeldt E, Serup J, Menne T: Effect of barrier perturbation on cutaneous salicylic acid penetration in human skin: in vivo pharmacokinetics using microdialysis and non-invasive quantification of barrier function. Br J Dermatol. 1999 Apr;140(4):739-48. [10233334 ]
  14. Paweska JT, Barnard BJ, Williams R: The use of sucrose-acetone-extracted Rift Valley fever virus antigen derived from cell culture in an indirect enzyme-linked immunosorbent assay and haemagglutination-inhibition test. Onderstepoort J Vet Res. 1995 Dec;62(4):227-33. [8668320 ]
  15. Bird AR, Kossew B, Mulligan TP, Jacobs P: Regional thromboplastin standardisation using a human brain extract. S Afr Med J. 1989 Jun 3;75(11):538-40. [2727843 ]
  16. Kalapos MP: Possible physiological roles of acetone metabolism in humans. Med Hypotheses. 1999 Sep;53(3):236-42. [10580530 ]