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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-11 00:41:42 UTC
Update Date2018-05-20 00:23:29 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 exists as a liquid, soluble (in water), and a very weakly acidic compound (based on its pKa). Hydroxyacetone has been detected in multiple biofluids, such as feces and urine. Hydroxyacetone participates in a number of enzymatic reactions. In particular, hydroxyacetone can be biosynthesized from acetone. Hydroxyacetone can also be converted into hydroxyacetone phosphate. Outside of the human body, hydroxyacetone can be found in a number of food items such as apple, strawberry, vaccinium (blueberry, cranberry, huckleberry), and kohlrabi. This makes hydroxyacetone a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
1-Hydroxy-2-propanoneChEBI
2-Ketopropyl alcoholChEBI
AcetolChEBI
Acetone alcoholChEBI
MethylketolChEBI
Pyruvic alcoholChEBI
PyruvinalcoholChEBI
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
DescriptionThis compound 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-07305dfad59d2227ffa7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-2534cfaae5c1ba708730View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0930000000-279a3f07932eb1839074View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0920000000-f1af25b38da545edc6c5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-31f525aaa70eed911510View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01rb-2900000000-bbb084ba481440566b91View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-b22d81e8da17e3f02d19View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-07305dfad59d2227ffa7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-2534cfaae5c1ba708730View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0930000000-279a3f07932eb1839074View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0920000000-f1af25b38da545edc6c5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-31f525aaa70eed911510View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01rb-2900000000-bbb084ba481440566b91View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-b22d81e8da17e3f02d19View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5e6801cf968784a5b9deView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gi-9300000000-e781920c2fc8ee89a28aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-535f26482c157dec5ff5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9000000000-9f6cd14ffcf61c467363View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-4b977c4569c666841170View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-359666943b9e9621209cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-67ac069288bf16663cf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1ad0fc4aef1abc1d687fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-50a216336c293bf1b3baView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Newborn (0-30 days old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected and Quantified3 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
UrineDetected but not Quantified Adult (>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
FoodDB IDFDB030646
KNApSAcK IDC00019558
Chemspider ID21106125
KEGG Compound IDC05235
BioCyc IDACETOL
BiGG IDNot Available
Wikipedia LinkHydroxyacetone
METLIN IDNot Available
PubChem Compound8299
PDB IDNot Available
ChEBI ID27957
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Casazza JP, Felver ME, Veech RL: The metabolism of acetone in rat. J Biol Chem. 1984 Jan 10;259(1):231-6. [PubMed:6706932 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  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