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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-11 00:41:42 UTC
Update Date2020-04-09 19:15:52 UTC
HMDB IDHMDB0006961
Secondary Accession Numbers
  • HMDB06961
Metabolite Identification
Common NameHydroxyacetone
DescriptionHydroxyacetone, also known as acetol or acetone alcohol, belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group. Hydroxyacetone is an extremely weak basic (essentially neutral) compound (based on its pKa). Hydroxyacetone exists in all living organisms, ranging from bacteria to humans. Hydroxyacetone is a sweet, caramellic, and ethereal tasting compound. Outside of the human body, hydroxyacetone has been detected, but not quantified in, several different foods, such as bog bilberries, cardoons, amaranths, black salsifies, and komatsuna. This could make hydroxyacetone a potential biomarker for the consumption of these foods. Hydroxyacetone is an intermediate in glycine, serine, and threonine metabolism.
Structure
Data?1586459752
Synonyms
ValueSource
1-Hydroxy-2-propanoneChEBI
2-Ketopropyl alcoholChEBI
AcetolChEBI
Acetone alcoholChEBI
MethylketolChEBI
Pyruvic alcoholChEBI
PyruvinalcoholChEBI
1-Hydroxy-2-acetoneHMDB
1-HydroxyacetoneHMDB
2-OxopropanolHMDB
AcetylcarbinolHMDB
AcetylmethanolHMDB
HydroxyacetoneHMDB
Hydroxymethyl methyl ketoneHMDB
HydroxypropanoneHMDB
alpha-HydroxyacetoneHMDB
α-HydroxyacetoneHMDB
Chemical FormulaC3H6O2
Average Molecular Weight74.0785
Monoisotopic Molecular Weight74.036779436
IUPAC Name1-hydroxypropan-2-one
Traditional Nameacetone alcohol
CAS Registry Number116-09-6
SMILES
CC(=O)CO
InChI Identifier
InChI=1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3
InChI KeyXLSMFKSTNGKWQX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydroxy ketones
Alternative Parents
Substituents
  • Alpha-hydroxy ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-17 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility680 g/LALOGPS
logP-1ALOGPS
logP-0.71ChemAxon
logS0.96ALOGPS
pKa (Strongest Acidic)13.88ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.9 m³·mol⁻¹ChemAxon
Polarizability7.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-07305dfad59d2227ffa7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-2534cfaae5c1ba708730Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0930000000-279a3f07932eb1839074Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0920000000-f1af25b38da545edc6c5Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-31f525aaa70eed911510Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01rb-2900000000-bbb084ba481440566b91Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-b22d81e8da17e3f02d19Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-07305dfad59d2227ffa7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-2534cfaae5c1ba708730Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0930000000-279a3f07932eb1839074Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0920000000-f1af25b38da545edc6c5Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-31f525aaa70eed911510Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01rb-2900000000-bbb084ba481440566b91Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-b22d81e8da17e3f02d19Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5e6801cf968784a5b9deSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gi-9300000000-e781920c2fc8ee89a28aSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 3V, positivesplash10-00di-9000000000-2d613d85b2a9ab4b81c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-00di-9000000000-8aac708a68b987439caeSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-00di-9000000000-7aa091c76f3b2e3533f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-00di-9000000000-a96f1f74ed0a81fc555bSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-05fr-9000000000-9e9863e2481fe663a1c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0ab9-9000000000-24d5b9ab081d2ab1dc4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-0a4i-9000000000-bf699c4edab22a9c3392Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-0a4i-9000000000-06ca82c23199feec7913Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 11V, positivesplash10-0a4i-9000000000-6063e22276e13798069cSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0a4i-9000000000-df73e7e99651b56301bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 13V, positivesplash10-0a4i-9000000000-cab5dcbf47489b84ed56Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 14V, positivesplash10-0a4i-9000000000-490e579ce5b7ee61e4b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 15V, positivesplash10-0a4i-9000000000-82946f673383e2e48eedSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-0a4i-9000000000-9e922e16d939cec82078Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 17V, positivesplash10-0a4i-9000000000-e9f30d809fd20007a0d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 18V, positivesplash10-0a6r-9000000000-5125f6367687313ab7e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 19V, positivesplash10-0a6r-9000000000-81a018ab2528282c82bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-0a6r-9000000000-3dd73306f979d472425eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-535f26482c157dec5ff5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9000000000-9f6cd14ffcf61c467363Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-4b977c4569c666841170Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-359666943b9e9621209cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-67ac069288bf16663cf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1ad0fc4aef1abc1d687fSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-50a216336c293bf1b3baSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified3 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Associated OMIM IDs
  • 601313 (Autosomal dominant polycystic kidney disease)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012041
KNApSAcK IDC00019558
Chemspider ID21106125
KEGG Compound IDC05235
BioCyc IDACETOL
BiGG IDNot Available
Wikipedia LinkHydroxyacetone
METLIN IDNot Available
PubChem Compound8299
PDB IDNot Available
ChEBI ID27957
Food Biomarker OntologyNot Available
VMH IDACETOL
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kelley JJ, Dekker EE: D-1-amino-2-propanol:NAD+ oxidoreductase. Purification and general properties of the large molecular form of the enzyme from Escherichia coli K12. J Biol Chem. 1984 Feb 25;259(4):2124-9. [PubMed:6365902 ]
  2. WERLE E, STIESS P: [Quantitative determination of acetol, with special reference to its formation in alkaline sugar decomposition]. Biochem Z. 1951;321(6):485-91. [PubMed:14858384 ]
  3. Kasai H, Nishimura S: Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Res. 1984 Feb 24;12(4):2137-45. [PubMed:6701097 ]
  4. Yamada-Onodera K, Ono K, Tani Y: Purification and characterization of an enzyme that has dihydroxyacetone-reducing activity from methanol-grown Hansenula ofunaensis. J Biosci Bioeng. 1999;88(2):148-52. [PubMed:16232589 ]
  5. Hatanaka Y, Kudo T, Miyataka M, Kobayashi O, Higashihara M, Hiyama K: Asymmetric reduction of hydroxyacetone to propanediol in immobilized halotolerant microalga Dunaliella parva. J Biosci Bioeng. 1999;88(3):281-6. [PubMed:16232612 ]
  6. Casazza JP, Felver ME, Veech RL: The metabolism of acetone in rat. J Biol Chem. 1984 Jan 10;259(1):231-6. [PubMed:6706932 ]
  7. HUGGINS CG, MILLER ON: The quantitative determination of acetol. J Biol Chem. 1956 Aug;221(2):711-8. [PubMed:13357464 ]
  8. SELLINGER OZ, MILLER ON: The phosphorylation of acetol. Biochim Biophys Acta. 1959 Nov;36:266-8. [PubMed:14444756 ]
  9. Ishikawa T, Aikawa T, Ohata E, Iseki T, Maeda S, Matsuo T, Fujino T, Saito S: Two-directional elaboration of hydroxyacetone under thermodynamically controlled conditions: allylation or 2-propynylation and aldol reaction. J Org Chem. 2007 Jan 19;72(2):435-41. [PubMed:17221959 ]
  10. Yaylayan VA, Keyhani A: Origin of carbohydrate degradation products in L-Alanine/D-[(13)C]glucose model systems. J Agric Food Chem. 2000 Jun;48(6):2415-9. [PubMed:10888560 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Does not exhibit retinol dehydrogenase (RDH) activity in vitro
Gene Name:
RDH13
Uniprot ID:
Q8NBN7
Molecular weight:
35931.8