Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000484
Identification
Name: Acetoin
Description:Acetoin 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 Pseudomonas aeruginosa. Pseudomonas aeruginosa 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
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
Average Molecular Weight: 88.1051
Monoisotopic Molecular Weight: 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
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.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbonyl compounds
Sub ClassAcyloins
Direct Parent Acyloins
Alternative Parents
Substituents
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic 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 Solubility473.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.39 m3·mol-1ChemAxon
Polarizability9.14 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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 Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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