Identification
ECMDB ID: ECMDB21446
Name: Diacetyl
Description: Diacetyl 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
Download: MOL | SDF | SMILES | InChI
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
Chemical Formula:
C4H6O2
Weight: Average: 86.0892
Monoisotopic: 86.036779436
InChI Key: InChIKey=QSJXEFYPDANLFS-UHFFFAOYSA-N
InChI:
InChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3
Plain Text
CAS number: 431-03-8
IUPAC Name:
butane-2,3-dione
Traditional IUPAC Name:
diacetyl
SMILES:
CC(=O)C(C)=O
Plain Text
Chemical Taxonomy
Kingdom: Organic Compounds
Super Class: Aliphatic Acyclic Compounds
Class: Carbonyl Compounds
Sub Class: Ketones
Other Descriptors:
  • a small molecule(Cyc)
  • alpha-diketone(ChEBI)
Substituents: Not Available
Direct Parent: Alpha-Diketones
Physical Properties
State: Liquid
Charge: 0
Melting point: -2.4 °C
Experimental Properties:
Property Value Source
Water Solubility: 200 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] PhysProp
LogP: -1.34 [HANSCH,C ET AL. (1995)] PhysProp
Predicted Properties:
Property Value Source
Water Solubility: 1.29e+02 g/l ALOGPS
LogP: 0.07 ALOGPS
LogP: 0.4 ChemAxon Molconvert
LogS: 0.18 ALOGPS
pKa: Not Available ChemAxon Molconvert
Hydrogen Acceptor Count: 2 ChemAxon Molconvert
Hydrogen Donor Count: 0 ChemAxon Molconvert
Polar Surface Area: 34.14 A2 ChemAxon Molconvert
Rotatable Bond Count: 1 ChemAxon Molconvert
Refractivity: 21.5 ChemAxon Molconvert
Polarizability: 8.4 ChemAxon Molconvert
Biological Properties
Cellular Locations:
  • Cytoplasm
Pathways: Not Available
Ecocyc Pathways: Not Available
Concentrations
Not Available
Spectra
MS/MS Spectrum Quattro_QQQ 10 view
MS/MS Spectrum Quattro_QQQ 25 view
MS/MS Spectrum Quattro_QQQ 40 view
MS/MS Spectrum EI-B (HITACHI M-80B) view
MS/MS Spectrum EI-B (HITACHI RMU-7M) view
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. Pubmed: 17765195 Link_out
  • 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 Link_out
Synthesis Reference: Not Available
External Links:
Resource Link
CHEBI ID: 16583 Link_out
HMDB ID: HMDB03407 Link_out
Pubchem Compound ID: 650 Link_out
Kegg ID: C00741 Link_out
ChemSpider ID: 630 Link_out
Wikipedia: Diacetyl Link_out

Enzymes
Not Available

Transporters
Not Available