Record Information
Creation Date2012-08-09 09:16:16 -0600
Update Date2015-09-13 15:15:33 -0600
Accession NumberECMDB21446
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.
  • 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
CAS number:431-03-8
IUPAC Name:butane-2,3-dione
Traditional IUPAC Name:diacetyl
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassKetones
Direct ParentAlpha-diketones
Alternative Parents
  • Alpha-diketone
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
Melting point:-2.4 °C
Experimental Properties:
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
Water Solubility129.0 mg/mLALOGPS
pKa (Strongest Acidic)15.98ChemAxon
pKa (Strongest Basic)-8.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.54 m3·mol-1ChemAxon
Polarizability8.41 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Not Available
Spectra:LC-MS/MSPredicted LC-MS/MSMS1D NMR
  • Espinosa-Mansilla A, Duran-Meras I, Salinas F: High-performance liquid chromatographic-fluorometric determination of glyoxal, methylglyoxal, and diacetyl in urine by prederivatization to pteridinic rings. Anal Biochem. 1998 Jan 15;255(2):263-73. Pubmed: 9451513
  • Hayes BK, Varki A: O-acetylation and de-O-acetylation of sialic acids. Sialic acid esterases of diverse evolutionary origins have serine active sites and essential arginine residues. J Biol Chem. 1989 Nov 15;264(32):19443-8. Pubmed: 2509478
  • Lombardo D, Campese D, Multigner L, Lafont H, De Caro A: On the probable involvement of arginine residues in the bile-salt-binding site of human pancreatic carboxylic ester hydrolase. Eur J Biochem. 1983 Jun 15;133(2):327-33. Pubmed: 6852044
  • Mehta RC, Hogan TF, Mardmomen S, Ma JK: Chromatographic studies of mitomycin C degradation in albumin microspheres. J Chromatogr. 1988 Sep 9;430(2):341-9. Pubmed: 3148622
  • Ostap EM: 2,3-Butanedione monoxime (BDM) as a myosin inhibitor. J Muscle Res Cell Motil. 2002;23(4):305-8. Pubmed: 12630704
  • Peretti E, Karlaganis G, Lauterburg BH: Acetylation of acetylhydrazine, the toxic metabolite of isoniazid, in humans. Inhibition by concomitant administration of isoniazid. J Pharmacol Exp Ther. 1987 Nov;243(2):686-9. Pubmed: 3681700
  • Sohaskey CD, Barbour AG: Esterases in serum-containing growth media counteract chloramphenicol acetyltransferase activity in vitro. Antimicrob Agents Chemother. 1999 Mar;43(3):655-60. Pubmed: 10049283
  • Sokolchik I, Tanabe T, Baldi PF, Sze JY: Polymodal sensory function of the Caenorhabditis elegans OCR-2 channel arises from distinct intrinsic determinants within the protein and is selectively conserved in mammalian TRPV proteins. J Neurosci. 2005 Jan 26;25(4):1015-23. Pubmed: 15673683
  • 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
  • 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:Xu, Ping; Chen, Hong; Du, Yi; Chen, Wanqiu; Xiao, Zijun. Method of preparation diacetyl by oxidization. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
CHEBI ID:16583
Pubchem Compound ID:650
Kegg ID:C00741
ChemSpider ID:630
BioCyc ID:Not Available