Acetoin (ECMDB03243) (M2MDB000484)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2012-05-31 13:58:11 -0600
Update Date2015-09-13 12:56:12 -0600
Secondary Accession Numbers
  • ECMDB03243
Identification
Name:Acetoin
DescriptionAcetoin is a chemical compound with the formula 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. Acetoin is a product of fermentation. It is a component of the butanediol cycle in E. coli. Escherichia coli pyruvate oxidase (POXEC) requires FAD both for the oxidative decarboxylation of pyruvate to acetate and CO2 and for the formation of acetoin from pyruvate and acetaldehyde. [PMID:8424670]
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (R)-2-acetoin
  • (R)-3-hydroxy-2-butanone
  • (R)-3-hydroxybutan-2-one
  • (R)-acetoin
  • (R)-dimethylketol
  • 1-Hydroxyethyl methyl ketone
  • 2,3-Butanolone
  • 2-Acetoin
  • 2-Butanol-3-one
  • 2-Hydroxy-3-butanone
  • 2-Hydroxy-3-oxobutane
  • 3-Hydroxy-2-Butanone
  • 3-Hydroxy-2-butanone (acetoin)
  • 3-Hydroxybutan-2-one
  • 3-Hydroxyl-2-butanone
  • Acetoine
  • Acetyl methyl carbinol
  • Acetylmethyl-Methanol
  • B-oxobutane
  • Beta-Oxobutane
  • Dimethylketol
  • β-Oxobutane
Chemical Formula:C4H8O2
Weight:Average: 88.1051
Monoisotopic: 88.0524295
InChI Key:ROWKJAVDOGWPAT-UHFFFAOYSA-N
InChI:InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3
CAS number:513-86-0
IUPAC Name:3-hydroxybutan-2-one
Traditional IUPAC Name:acetoin
SMILES:CC(O)C(C)=O
Chemical Taxonomy
Description 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
Physical Properties
State:Liquid
Charge:0
Melting point:15 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000000 mg/L at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-0.216PhysProp
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
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0005-9000000000-62904abc1fc33ec40dfaView in MoNA
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-f6eb75cfea26ad71fa57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-9a52f81ee53395623632View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-9000000000-c5e178ac425b271910a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-f43d429661b310e7148aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-160fee6a321df2fa7b05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4b3590a18d40d4d58a01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-bc260446b65990487a67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-0c841ea6edf8e31c3df0View 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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Bertagnolli, B. L., Hager, L. P. (1993). "Role of flavin in acetoin production by two bacterial pyruvate oxidases." Arch Biochem Biophys 300:364-371. Pubmed: 8424670
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15688
HMDB IDHMDB03243
Pubchem Compound ID179
Kegg IDC00466
ChemSpider ID21105851
WikipediaAcetoin
BioCyc IDNot Available

Enzymes

Protein Details
1. Pyruvate dehydrogenase [cytochrome]
General function:
Involved in magnesium ion binding
Specific function:
Pyruvate + ferricytochrome b1 + H(2)O = acetate + CO(2) + ferrocytochrome b1
Gene Name:
poxB
Uniprot ID:
P07003
Molecular weight:
62011
Reactions
Pyruvate + ubiquinone + H(2)O = acetate + CO(2) + ubiquinol.