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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:11:42 UTC
Update Date2022-03-07 02:54:25 UTC
HMDB IDHMDB0035243
Secondary Accession Numbers
  • HMDB35243
Metabolite Identification
Common Name1-Phenyl-1,2-propanedione
Description1-Phenyl-1,2-propanedione, also known as acetyl benzoyl or phenyl methyl diketone, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. 1-Phenyl-1,2-propanedione is a buttery, honey, and pepper tasting compound. 1-Phenyl-1,2-propanedione has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 1-phenyl-1,2-propanedione a potential biomarker for the consumption of these foods. 1-Phenyl-1,2-propanedione is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 1-Phenyl-1,2-propanedione.
Structure
Data?1563862688
Synonyms
ValueSource
1-Phenyl-1,2-dioxopropaneChEBI
3-Phenyl-2,3-propanedioneChEBI
Acetyl benzoylChEBI
AcetylbenzoylChEBI
Benzoyl methyl ketoneChEBI
BenzoylacetylChEBI
Methyl phenyl diketoneChEBI
Methyl phenyl glyoxalChEBI
MethylphenylglyoxalChEBI
Phenyl methyl diketoneChEBI
PhenylmethyldiketoneChEBI
PyruvophenoneChEBI
1-Phenyl-1,2-propandioneHMDB
1-Phenylpropane-1,2-dioneHMDB
FEMA 3226HMDB
Chemical FormulaC9H8O2
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
IUPAC Name1-phenylpropane-1,2-dione
Traditional Nameacetyl benzoyl
CAS Registry Number579-07-7
SMILES
CC(=O)C(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6H,1H3
InChI KeyBVQVLAIMHVDZEL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aryl ketone
  • Benzoyl
  • Alpha-diketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 20 °CNot Available
Boiling Point103.00 to 105.00 °C. @ 14.00 mm HgThe Good Scents Company Information System
Water Solubility2.6 mg/mL at 20 °CNot Available
LogP1.169 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.92 g/LALOGPS
logP0.94ALOGPS
logP1.82ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)16.92ChemAxon
pKa (Strongest Basic)-8.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.81 m³·mol⁻¹ChemAxon
Polarizability15.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.20331661259
DarkChem[M-H]-129.7931661259
DeepCCS[M+H]+132.77830932474
DeepCCS[M-H]-129.9630932474
DeepCCS[M-2H]-166.15230932474
DeepCCS[M+Na]+141.55530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Phenyl-1,2-propanedioneCC(=O)C(=O)C1=CC=CC=C11817.4Standard polar33892256
1-Phenyl-1,2-propanedioneCC(=O)C(=O)C1=CC=CC=C11125.0Standard non polar33892256
1-Phenyl-1,2-propanedioneCC(=O)C(=O)C1=CC=CC=C11217.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Phenyl-1,2-propanedione,1TMS,isomer #1C=C(O[Si](C)(C)C)C(=O)C1=CC=CC=C11438.5Semi standard non polar33892256
1-Phenyl-1,2-propanedione,1TMS,isomer #1C=C(O[Si](C)(C)C)C(=O)C1=CC=CC=C11374.0Standard non polar33892256
1-Phenyl-1,2-propanedione,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC=C11664.0Semi standard non polar33892256
1-Phenyl-1,2-propanedione,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC=C11566.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1-Phenyl-1,2-propanedione EI-B (Non-derivatized)splash10-0a6r-9500000000-0ad1ba839fdf36b669322017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Phenyl-1,2-propanedione EI-B (Non-derivatized)splash10-0a6r-9500000000-0ad1ba839fdf36b669322018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Phenyl-1,2-propanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-0995a26dda9c3bc5dbec2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Phenyl-1,2-propanedione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 10V, Positive-QTOFsplash10-000t-0900000000-23a8b7ff76e850b79b3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 20V, Positive-QTOFsplash10-001j-0900000000-fb650b96ad441c16bed72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 40V, Positive-QTOFsplash10-0pc0-6900000000-6693984118df075408bc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 10V, Negative-QTOFsplash10-0002-0900000000-02e11fb73ce9229aee3c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 20V, Negative-QTOFsplash10-052b-0900000000-11eb6ccaabf1484aba792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 40V, Negative-QTOFsplash10-0zi0-2900000000-2ba7d36b3c9387c119072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 10V, Positive-QTOFsplash10-0002-1900000000-9c4104ddeb2be69ca7cb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 20V, Positive-QTOFsplash10-0a4i-3900000000-978783f78075cb7042832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 40V, Positive-QTOFsplash10-004i-9100000000-d4f8904f7ef35220495f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 10V, Negative-QTOFsplash10-0002-0900000000-f55a05e2292ed812db8a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 20V, Negative-QTOFsplash10-056s-6900000000-d8f40443c310f8ed55fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 40V, Negative-QTOFsplash10-004i-9100000000-e37b1d1d767deab85b702021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013903
KNApSAcK IDNot Available
Chemspider ID10885
KEGG Compound IDC17268
BioCyc IDCPD-9949
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11363
PDB IDNot Available
ChEBI ID63552
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1035591
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .