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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-11 00:41:42 UTC
Update Date2021-09-07 17:05:27 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 in all living organisms, ranging from bacteria to humans. Hydroxyacetone is a sweet, caramel, and ethereal tasting compound. 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
Hydroxymethyl methyl ketoneHMDB
HydroxypropanoneHMDB
alpha-HydroxyacetoneHMDB
Α-hydroxyacetoneHMDB
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 Molecular Properties
PropertyValueReference
Melting Point-17 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available113.04131661259
DarkChem[M-H]-PredictedNot Available106.51231661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Hydroxyacetone,1TMS,#1883.838https://arxiv.org/abs/1905.12712
Hydroxyacetone,1TMS,#2927.9https://arxiv.org/abs/1905.12712
Hydroxyacetone,1TMS,#3843.8136https://arxiv.org/abs/1905.12712
Hydroxyacetone,1TBDMS,#11099.9784https://arxiv.org/abs/1905.12712
Hydroxyacetone,1TBDMS,#21152.2369https://arxiv.org/abs/1905.12712
Hydroxyacetone,1TBDMS,#31068.5153https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-07305dfad59d2227ffa72017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-2534cfaae5c1ba7087302017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0930000000-279a3f07932eb18390742017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0920000000-f1af25b38da545edc6c52017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-31f525aaa70eed9115102017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01rb-2900000000-bbb084ba481440566b912017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-b22d81e8da17e3f02d192017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-07305dfad59d2227ffa72018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-2534cfaae5c1ba7087302018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0930000000-279a3f07932eb18390742018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0920000000-f1af25b38da545edc6c52018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-31f525aaa70eed9115102018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01rb-2900000000-bbb084ba481440566b912018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-b22d81e8da17e3f02d192018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5e6801cf968784a5b9de2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gi-9300000000-e781920c2fc8ee89a28a2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-50a216336c293bf1b3ba2015-03-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - QqQ 3V, positivesplash10-00di-9000000000-2d613d85b2a9ab4b81c42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-00di-9000000000-8aac708a68b987439cae2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-00di-9000000000-7aa091c76f3b2e3533f62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-00di-9000000000-a96f1f74ed0a81fc555b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-05fr-9000000000-9e9863e2481fe663a1c22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0ab9-9000000000-24d5b9ab081d2ab1dc4e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-0a4i-9000000000-bf699c4edab22a9c33922020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-0a4i-9000000000-06ca82c23199feec79132020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 11V, positivesplash10-0a4i-9000000000-6063e22276e13798069c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0a4i-9000000000-df73e7e99651b56301bf2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 13V, positivesplash10-0a4i-9000000000-cab5dcbf47489b84ed562020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 14V, positivesplash10-0a4i-9000000000-490e579ce5b7ee61e4b62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 15V, positivesplash10-0a4i-9000000000-82946f673383e2e48eed2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-0a4i-9000000000-9e922e16d939cec820782020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 17V, positivesplash10-0a4i-9000000000-e9f30d809fd20007a0d52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 18V, positivesplash10-0a6r-9000000000-5125f6367687313ab7e12020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 19V, positivesplash10-0a6r-9000000000-81a018ab2528282c82bf2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-0a6r-9000000000-3dd73306f979d472425e2020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-359666943b9e9621209c2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-67ac069288bf16663cf72015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1ad0fc4aef1abc1d687f2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-535f26482c157dec5ff52015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9000000000-9f6cd14ffcf61c4673632015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-4b977c4569c6668411702015-05-26View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)2015-03-12View Spectrum
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 IDNot Available
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