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Identification
YMDB IDYMDB00367
NameDiacetyl
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDiacetyl, also known as 2,3-butadione or dimethylglyoxal, belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. Thus, diacetyl is considered to be an oxygenated hydrocarbon lipid molecule. Diacetyl is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Diacetyl exists in all living species, ranging from bacteria to humans. Diacetyl is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2,3-Butadione
  • 2,3-Butandione
  • 2,3-Butanedione
  • 2,3-Diketobutane
  • 2,3-Dioxobutane
  • Acetoacetaldehyde
  • Biacetyl
  • Butadione
  • Butan-2,3-dione
  • Butane-2,3-dione
  • Butanedione
  • Butanedione [UN2346]
  • Diacetyl
  • Dimethyl diketone
  • Dimethyl glyoxal
  • Dimethylglyoxal
  • Dimethyldiketone
  • Diketobutane
  • 2,3 Butanedione
CAS number431-03-8
WeightAverage: 86.0892
Monoisotopic: 86.036779436
InChI KeyQSJXEFYPDANLFS-UHFFFAOYSA-N
InChIInChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3
IUPAC Namebutane-2,3-dione
Traditional IUPAC Namediacetyl
Chemical FormulaC4H6O2
SMILES[H]C([H])([H])C(=O)C(=O)C([H])([H])[H]
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-diketones
Alternative Parents
Substituents
  • Alpha-diketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-2.4 °C
Experimental Properties
PropertyValueReference
Water Solubility200 mg/mL at 15 oC [YALKOWSKY,SH & HE,Y (2003)]PhysProp
LogP-1.34 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility129 g/LALOGPS
logP0.07ALOGPS
logP0.4ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)15.98ChemAxon
pKa (Strongest Basic)-8.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.54 m³·mol⁻¹ChemAxon
Polarizability8.41 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
ButterFDB011930
CaramelFDB011930
CreamyFDB011930
OilyFDB011930
PungentFDB011930
StrongFDB011930
SweetFDB011930
SMPDB PathwaysNot Available
KEGG Pathways
Butanoate metabolismec00650 Map00650
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-eeaaf8aa838a1d6a7ddeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-622030119adee3079d84JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-eeaaf8aa838a1d6a7ddeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-622030119adee3079d84JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-58f4b3973bdf0094a5e3JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-4e7132ef8eb6971544b1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00r5-9000000000-0cc5c90a4394d550268fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-06dj-9000000000-a74bfecfcdb93a5c3e07JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-eeaaf8aa838a1d6a7ddeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-171c3774c90fd50b6d6bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-e8c63126caa0f371f336JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-82affa84acc0579c193bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-f63598734c0af05eb392JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-e8c63126caa0f371f336JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-82affa84acc0579c193bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-f63598734c0af05eb392JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2599bbcd002f75cefa1dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-1171c0cf98959e7315c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-7dcc0fc66bb1e551b332JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2599bbcd002f75cefa1dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-1171c0cf98959e7315c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-7dcc0fc66bb1e551b332JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-8d1a3988261033033e03JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
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.
External Links:
ResourceLink
CHEBI ID16583
HMDB IDHMDB03407
Pubchem Compound ID650
Kegg IDC00741
ChemSpider ID630
FOODB IDFDB011930
WikipediaDiacetyl
BioCyc IDNN-DIACETYLCHITOBIOSYLDIPHOSPHODOLICHO

Enzymes

General function:
Involved in zinc ion binding
Specific function:
Catalyzes the irreversible reduction of 2,3-butanediol to (S)-acetoin in the presence of NADH (Potential)
Gene Name:
BDH2
Uniprot ID:
P39713
Molecular weight:
46098.19922
Reactions
(R)-acetoin + NAD(+) → diacetyl + NADH.
General function:
Involved in zinc ion binding
Specific function:
Catalyzes the irreversible reduction of 2,3-butanediol to (S)-acetoin in the presence of NADH
Gene Name:
BDH1
Uniprot ID:
P39714
Molecular weight:
41537.69922
Reactions
(R)-acetoin + NAD(+) → diacetyl + NADH.