Showing metabocard for Diacetyl (BMDB0003407)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:04:21 UTC
Update Date2020-06-04 18:59:54 UTC
BMDB IDBMDB0003407
Secondary Accession Numbers
  • BMDB03407
Metabolite Identification
Common NameDiacetyl
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 exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Diacetyl exists in all living species, ranging from bacteria to humans. Diacetyl is a potentially toxic compound. Diacetyl has been found to be associated with several diseases known as ulcerative colitis, nonalcoholic fatty liver disease, and crohn's disease; also diacetyl has been linked to the inborn metabolic disorders including celiac disease.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2,3-ButadioneChEBI
2,3-ButandioneChEBI
2,3-ButanedioneChEBI
2,3-DiketobutaneChEBI
2,3-DioxobutaneChEBI
BiacetylChEBI
Dimethyl glyoxalChEBI
DimethylglyoxalChEBI
2,3 ButanedioneMeSH
DiketobutaneMeSH
DimethyldiketoneMeSH
AcetoacetaldehydeHMDB
ButadioneHMDB
Butan-2,3-dioneHMDB
Butane-2,3-dioneHMDB
ButanedioneHMDB
Dimethyl diketoneHMDB
DiacetylChEBI
Chemical FormulaC4H6O2
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
IUPAC Namebutane-2,3-dione
Traditional Namediacetyl
CAS Registry Number431-03-8
SMILES
CC(=O)C(C)=O
InChI Identifier
InChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3
InChI KeyQSJXEFYPDANLFS-UHFFFAOYSA-N
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-2.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility200 mg/mL at 15 °CNot Available
LogP-1.34HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
  • Neuron
  • Ovary
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified0.13 +/- 0.19 mg/100g dry matter contentNot SpecifiedNot Specified
Normal
    • Brigitta Gaspardo...
 details
MilkDetected and Quantified0.23 +/- 0.23 mg/100g dry matter contentNot SpecifiedNot Specified
Normal
    • Brigitta Gaspardo...
 details
MilkDetected and Quantified0.00251 +/- 0.00203 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.00359 +/- 0.00239 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.0323 +/- 0.0587 uMNot SpecifiedNot Specified
Normal		 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
OvaryExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003407
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011930
KNApSAcK IDC00050437
Chemspider ID630
KEGG Compound IDC00741
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiacetyl
METLIN ID6921
PubChem Compound650
PDB IDNot Available
ChEBI ID16583
References
Synthesis ReferenceXu, 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)Not Available
General References
  1. Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77. [PubMed:12463694 ]
  2. Brigitta Gaspardo, Giuseppe Procida, Saša Volarič, Sandy Sgorlon & Bruno Stefanon (2009). Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009. Italian Journal of Animal Science .