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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-12 20:15:57 UTC
Update Date2019-07-23 05:45:46 UTC
HMDB IDHMDB0003407
Secondary Accession Numbers
  • HMDB03407
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 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 strong, sweet, and butter tasting compound. Outside of the human body, diacetyl is found, on average, in the highest concentration in kohlrabis. diacetyl has also been detected, but not quantified in, several different foods, such as nances, tartary buckwheats, tamarinds, pineapples, and celeriacs. This could make diacetyl a potential biomarker for the consumption of these foods. Diacetyl is a potentially toxic compound. Diacetyl has been found to be associated with several diseases such as crohn's disease, ulcerative colitis, and nonalcoholic fatty liver disease; also diacetyl has been linked to the inborn metabolic disorders including celiac disease.
Structure
Data?1563860746
Synonyms
ValueSource
2,3-ButadioneChEBI
2,3-ButandioneChEBI
2,3-ButanedioneChEBI
2,3-DiketobutaneChEBI
2,3-DioxobutaneChEBI
BiacetylChEBI
Dimethyl glyoxalChEBI
DimethylglyoxalChEBI
AcetoacetaldehydeHMDB
ButadioneHMDB
Butan-2,3-dioneHMDB
Butane-2,3-dioneHMDB
ButanedioneHMDB
Dimethyl diketoneHMDB
DimethyldiketoneHMDB
DiketobutaneHMDB
2,3 ButanedioneHMDB
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Industrial process:

Role

Industrial application:

Environmental role:

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
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
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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
  • Saliva
Tissue Locations
  • Gonads
  • Neuron
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Newborn (0-30 days old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified39261.603-345416.924 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected and Quantified0-1550872.0412 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011930
KNApSAcK IDNot Available
Chemspider ID630
KEGG Compound IDC00741
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiacetyl
METLIN ID6921
PubChem Compound650
PDB IDNot Available
ChEBI ID16583
Food Biomarker OntologyNot Available
VMH IDNot Available
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)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Ostap EM: 2,3-Butanedione monoxime (BDM) as a myosin inhibitor. J Muscle Res Cell Motil. 2002;23(4):305-8. [PubMed:12630704 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]