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Record Information
Version4.0
Creation Date2006-05-22 15:12:44 UTC
Update Date2017-09-27 08:24:20 UTC
HMDB IDHMDB0003243
Secondary Accession Numbers
  • HMDB03243
Metabolite Identification
Common NameAcetoin
DescriptionAcetoin is a product of fermentation. It is a component of the butanediol cycle in microorganisms. In mammals it is oxidized to carbon dioxide. -- Pubchem; '3-Hydroxybutanone, also known as acetoin or acetyl methyl carbinol, is a chemical compound composed of carbon, hydrogen and oxygen. Its formula is C4H8O2. It is a colourless or pale yellow to green yellow liquid with a pleasant buttery odour. It is used as a food flavoring and a fragrance. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
(S)-2-AcetoinChEBI
1-Hydroxyethyl methyl ketoneChEBI
2,3-ButanoloneChEBI
2-AcetoinChEBI
2-Hydroxy-3-butanoneChEBI
3-Hydroxy-2-butanoneChEBI
3-Hydroxybutan-2-oneChEBI
Acetyl methyl carbinolChEBI
DimethylketolChEBI
gamma-Hydroxy-beta-oxobutaneChEBI
g-Hydroxy-b-oxobutaneGenerator
γ-hydroxy-β-oxobutaneGenerator
(R)-2-AcetoinHMDB
(R)-3-Hydroxy-2-butanoneHMDB
(R)-3-Hydroxybutan-2-oneHMDB
(R)-AcetoinHMDB
(R)-DimethylketolHMDB
2-Butanol-3-oneHMDB
2-Hydroxy-3-oxobutaneHMDB
3-Hydroxyl-2-butanoneHMDB
AcetoineHMDB
b-OxobutaneHMDB
beta-OxobutaneHMDB
AcetylmethylcarbinolMeSH
3H-2b ButanoneMeSH
Chemical FormulaC4H8O2
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
IUPAC Name3-hydroxybutan-2-one
Traditional Nameacetoin
CAS Registry Number513-86-0
SMILES
CC(O)C(C)=O
InChI Identifier
InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3
InChI KeyROWKJAVDOGWPAT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAcyloins
Alternative Parents
Substituents
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Plant:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point15 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility473 g/LALOGPS
logP-0.66ALOGPS
logP-0.14ChemAxon
logS0.73ALOGPS
pKa (Strongest Acidic)13.72ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.39 m³·mol⁻¹ChemAxon
Polarizability9.14 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)splash10-0005-9000000000-62904abc1fc33ec40dfaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-be498c13cd64980f1f35View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00kf-9500000000-79fa75cf570cd4a3de14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006x-9000000000-3bc66270ca4dc0f2c444View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-ac710258a11f0566c38aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-94fbec9f0efb37d8aa39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0005-9000000000-eaafc4c4d8cb29864f1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-ebb7996f3f82cc069f12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9000000000-4043204b04ec3b5823ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9000000000-1e66901c3375433b1693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-9d60c7f29d91e72ce0bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-35eb749498333af99296View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-9000000000-ce5e7eaa33d4f9d4fa86View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0005-9000000000-74d60654cdf23dfc35acView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.06 +/- 1.54 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified0 - 126.48 ppmChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.497 +/- 2.989 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected and Quantified0 - 1025.01 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
UrineDetected and Quantified5.516 +/- 5.604 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011799
KNApSAcK IDNot Available
Chemspider ID21105851
KEGG Compound IDC00466
BioCyc IDCPD-255
BiGG IDNot Available
Wikipedia LinkAcetoin
METLIN ID103
PubChem Compound179
PDB IDNot Available
ChEBI ID15688
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hirooka EY, Muller EE, Freitas JC, Vicente E, Yoshimoto Y, Bergdoll MS: Enterotoxigenicity of Staphylococcus intermedius of canine origin. Int J Food Microbiol. 1988 Dec;7(3):185-91. [PubMed:3275321 ]
  2. Walker V, Mills GA: Urinary organic acid excretion by babies born before 33 weeks of gestation. Clin Chem. 1989 Jul;35(7):1460-6. [PubMed:2758593 ]
  3. Walker V, Mills GA, Hall MA, Lowes JA: Carbohydrate fermentation by gut microflora in preterm neonates. Arch Dis Child. 1989 Oct;64(10 Spec No):1367-73. [PubMed:2589871 ]
  4. Otsuka M, Ohmori S: Simple and sensitive determination of diacetyl and acetoin in biological samples and alcoholic drinks by gas chromatography with electron-capture detection. J Chromatogr. 1992 Jun 10;577(2):215-20. [PubMed:1400754 ]