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Record Information
Version	2.0
Creation Date	2012-08-09 09:16:16 -0600
Update Date	2015-09-13 15:15:33 -0600
Secondary Accession Numbers	ECMDB21446
Identification
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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0x976cfe5c> Close
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:	QSJXEFYPDANLFS-UHFFFAOYSA-N
InChI:	InChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3
CAS number:	431-03-8
IUPAC Name:	butane-2,3-dione
Traditional IUPAC Name:	diacetyl
SMILES:	CC(=O)C(C)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbonyl compounds
Direct Parent	Alpha-diketones
Alternative Parents	Organic oxides Hydrocarbon derivatives
Substituents	Alpha-diketone Organic oxide Hydrocarbon derivative Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	alpha-diketone (CHEBI:16583 ) Oxygenated hydrocarbons (LMFA12000012 ) a small molecule (DIACETYL )
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 129 g/L ALOGPS logP 0.07 ALOGPS logP 0.4 ChemAxon logS 0.18 ALOGPS pKa (Strongest Acidic) 15.98 ChemAxon pKa (Strongest Basic) -8.3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 34.14 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 21.54 m³·mol⁻¹ ChemAxon Polarizability 8.41 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-0006-9000000000-eeaaf8aa838a1d6a7dde View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-0006-9000000000-622030119adee3079d84 View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-0006-9000000000-eeaaf8aa838a1d6a7dde View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-0006-9000000000-622030119adee3079d84 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0006-9000000000-58f4b3973bdf0094a5e3 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-000i-9000000000-4e7132ef8eb6971544b1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-00r5-9000000000-0cc5c90a4394d550268f View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-06dj-9000000000-a74bfecfcdb93a5c3e07 View in MoNA LC-MS/MS LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive splash10-0006-9000000000-eeaaf8aa838a1d6a7dde View in MoNA LC-MS/MS LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive splash10-0006-9000000000-171c3774c90fd50b6d6b View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-001i-9000000000-6e218d8c4f1cb3a01254 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-0ufr-9000000000-c27bd416a10df3c9c1d3 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-001i-9000000000-49c29114e2316ba16f02 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 35V, Positive splash10-000i-9000000000-0c5000d8f4b14cdc5b05 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-9000000000-e8c63126caa0f371f336 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00kr-9000000000-82affa84acc0579c193b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udi-9000000000-f63598734c0af05eb392 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-9000000000-e8c63126caa0f371f336 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00kr-9000000000-82affa84acc0579c193b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udi-9000000000-f63598734c0af05eb392 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-9000000000-2599bbcd002f75cefa1d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000i-9000000000-1171c0cf98959e7315c6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-014i-9000000000-7dcc0fc66bb1e551b332 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-9000000000-2599bbcd002f75cefa1d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000i-9000000000-1171c0cf98959e7315c6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-014i-9000000000-7dcc0fc66bb1e551b332 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0006-9000000000-87bbaed151efac084591 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0006-9000000000-87bbaed151efac084591 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-87bbaed151efac084591 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-9000000000-ec20127c74818b1f634d View in MoNA MS Mass Spectrum (Electron Ionization) splash10-0006-9000000000-8d1a3988261033033e03 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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)
Links
External Links:	Resource Link CHEBI ID 16583 HMDB ID HMDB03407 Pubchem Compound ID 650 Kegg ID C00741 ChemSpider ID 630 Wikipedia Diacetyl BioCyc ID Not Available