Record Information
Version1.0
Creation date2010-04-08 22:09:57 UTC
Update date2019-11-26 03:06:03 UTC
Primary IDFDB012041
Secondary Accession Numbers
  • FDB030646
Chemical Information
FooDB Name1-Hydroxy-2-propanone
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. Hydroxyacetone has been detected, but not quantified in, several different foods, such as hyacinth beans, cottonseeds, horseradish, lemon balms, and cucumbers. This could make hydroxyacetone a potential biomarker for the consumption of these foods.
CAS Number116-09-6
Structure
Thumb
Synonyms
SynonymSource
1-Hydroxy-2-propanoneChEBI
2-Ketopropyl alcoholChEBI
AcetolChEBI
Acetone alcoholChEBI
MethylketolChEBI
Pyruvic alcoholChEBI
PyruvinalcoholChEBI
1-Hydroxyacetonebiospider
1-hydroxypropan-2-onebiospider
2-Oxopropanolbiospider
2-Propanone, 1-hydroxy-biospider
Acetol (van)biospider
ACETOL, 50% SOLNbiospider
Acetonyl alcoholdb_source
Acetylcarbinoldb_source
Acetylmethanolbiospider
CH3C(O)CH2OHbiospider
Hydroxy-2-propanonebiospider
Hydroxyacetonedb_source
Hydroxyacetone (acetol)biospider
Hydroxymethyl methyl ketonedb_source
hydroxypropan-2-onebiospider
Hydroxypropanonebiospider
Methanol, acetyl-biospider
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC3H6O2
IUPAC name1-hydroxypropan-2-one
InChI IdentifierInChI=1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3
InChI KeyXLSMFKSTNGKWQX-UHFFFAOYSA-N
Isomeric SMILESCC(=O)CO
Average Molecular Weight74.0785
Monoisotopic Molecular Weight74.036779436
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 48.64%; H 8.16%; O 43.20%DFC
Melting PointFp -17 approx.°DFC
Boiling PointBp150 96-97°DFC
Experimental Water Solubility1000 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd2020 1.08DFC
Refractive Indexn20D 1.4295DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-07305dfad59d2227ffa7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-2534cfaae5c1ba708730JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0930000000-279a3f07932eb1839074JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0920000000-f1af25b38da545edc6c5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-31f525aaa70eed911510JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01rb-2900000000-bbb084ba481440566b91JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-b22d81e8da17e3f02d19JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-07305dfad59d2227ffa7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-2534cfaae5c1ba708730JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0930000000-279a3f07932eb1839074JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-017j-0920000000-f1af25b38da545edc6c5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-31f525aaa70eed911510JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01rb-2900000000-bbb084ba481440566b91JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2950000000-b22d81e8da17e3f02d19JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5e6801cf968784a5b9deJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gi-9300000000-e781920c2fc8ee89a28aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-535f26482c157dec5ff5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9000000000-9f6cd14ffcf61c467363JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-4b977c4569c666841170JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-359666943b9e9621209cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-67ac069288bf16663cf7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1ad0fc4aef1abc1d687fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-50a216336c293bf1b3baJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID21106125
ChEMBL IDNot Available
KEGG Compound IDC05235
Pubchem Compound ID8299
Pubchem Substance IDNot Available
ChEBI ID27957
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06961
CRC / DFC (Dictionary of Food Compounds) IDHCS63-R:HCS63-R
EAFUS ID1721
Dr. Duke ID1-HYDROXY-PROPAN-2-ONE
BIGG IDNot Available
KNApSAcK IDC00019558
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1132561
SuperScent IDNot Available
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 / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Retinol dehydrogenase 13RDH13Q8NBN7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
pungent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramellic
  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.
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).