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Identification
ECMDB IDECMDB21446
NameDiacetyl
DescriptionDiacetyl is a natural by-product of secondary or malolactic fermentation. It is also a product of butanoate metabolism. It is a vicinal diketone (two C=O groups, side-by-side) with the molecular formula C4H6O2. It has a buttery aroma. Beer sometimes undergoes a diacetyl rest, which entails waiting two or three days after fermentation is complete, to allow the yeast to absorb the diacetyl it produced earlier in the fermentation cycle. The makers of some wines, such as chardonnay, deliberately promote the production of diacetyl because of the feel and flavors it imparts.
Structure
Thumb
Synonyms
  • 2,3-Butadione
  • 2,3-Butandione
  • 2,3-Butanedione
  • 2,3-Diketobutane
  • 2,3-Dioxobutane
  • 2,3-Dioxobutane, butadione
  • Acetoacetaldehyde
  • Biacetyl
  • Butadione
  • Butan-2,3-dione
  • Butane-2,3-dione
  • Butanedione
  • Butanedione [UN2346]
  • Dimethyl diketone
  • Dimethyl glyoxal
  • Dimethylglyoxal
CAS number431-03-8
WeightAverage: 86.0892
Monoisotopic: 86.036779436
InChI KeyInChIKey=QSJXEFYPDANLFS-UHFFFAOYSA-N
InChIInChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3
IUPAC Namebutane-2,3-dione
Traditional IUPAC Namediacetyl
Chemical FormulaC4H6O2
SMILESCC(=O)C(C)=O
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassCarbonyl Compounds
Sub ClassKetones
Other Descriptors
  • a small molecule(Cyc)
  • alpha-diketone(ChEBI)
Substituents
  • a small molecule(Cyc)
  • alpha-diketone(ChEBI)
Physical Properties
StateLiquid
Charge0
Melting point-2.4 °C
Experimental Properties
PropertyValueReference
Water Solubility200 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-1.34 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility129.0ALOGPS
logP0.07ALOGPS
logP0.4ChemAxon
logS0.18ALOGPS
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.54 m3·mol-1ChemAxon
Polarizability8.41 Å3ChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
PathwaysNot Available
Ecocyc PathwaysNot Available
Concentrations
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureCitationComment
Details describing the conversion of literature concentrations can be found here.
Spectra
SpectraMS/MSMS1D NMR
References
References:
  • 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 370:17-25.17765195
  • 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 80:2939-2948.18331064
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID:16583
HMDB ID:HMDB03407
Pubchem Compound ID:650
Kegg ID:C00741
ChemSpider ID:630
Wikipedia:Diacetyl