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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 20:57:49 UTC
Update Date2020-05-13 15:19:15 UTC
HMDB IDHMDB0035915
Secondary Accession Numbers
  • HMDB35915
Metabolite Identification
Common NameSulcatone
DescriptionSulcatone, also known as methylheptenone or fema 2707, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, sulcatone is considered to be an oxygenated hydrocarbon lipid molecule. Sulcatone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sulcatone exists in all eukaryotes, ranging from yeast to humans. Sulcatone is a mushroom, pepper, and rubber tasting compound. Outside of the human body, Sulcatone is found, on average, in the highest concentration within gingers and peppermints. Sulcatone has also been detected, but not quantified in, cloves and watermelons. This could make sulcatone a potential biomarker for the consumption of these foods. Sulcatone, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, asthma, and crohn's disease; sulcatone has also been linked to the inborn metabolic disorder celiac disease.
Structure
Data?1589383154
Synonyms
ValueSource
6-Methyl-5-hepten-2-oneChEBI
6-Methylhept-5-en-2-oneChEBI
MethylheptenoneKegg
2-Methyl-2-hepten-6-oneHMDB
2-Methyl-6-heptenoneHMDB
2-Methyl-6-oxo-2-hepteneHMDB
2-Methylhept-2-en-6-oneHMDB
2-oxo-6-Methylhept-5-eneHMDB
6-Methyl hept-5-en-2-oneHMDB
6-Methyl-5-heptene-2-oneHMDB
6-Methylheptan-5-ene-2-oneHMDB
FEMA 2707HMDB
PrenylacetoneHMDB
6-Methylhept-5-ene-2-oneHMDB
SulcatoneMeSH
Chemical FormulaC8H14O
Average Molecular Weight126.1962
Monoisotopic Molecular Weight126.10446507
IUPAC Name6-methylhept-5-en-2-one
Traditional Name6-methyl-5-hepten-2-one
CAS Registry Number110-93-0
SMILES
CC(C)=CCCC(C)=O
InChI Identifier
InChI=1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3
InChI KeyUHEPJGULSIKKTP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-67 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.54 g/LALOGPS
logP2.01ALOGPS
logP2.02ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity40.02 m³·mol⁻¹ChemAxon
Polarizability15.53 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-52448d8f5e75dfce2601Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-52448d8f5e75dfce2601Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-2a4a7d0cf2baca776c97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2900000000-1c6462dfab5ba93de56aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-9800000000-3a5a239448b9074b6329Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9000000000-b4f774fa9c89ef7f85a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-77ea35597ceee3c16d4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4900000000-223aa0397cf0652e4556Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-7fc0a9ab1c35aabebd1aSpectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-a1a351553f2efdaaf3bcSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 Adult (>18 years old)BothNormal 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 Quantified0-84075.432 nmol/g wet fecesChildren (1-13 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
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not Quantified Children (1-13 years old)Not SpecifiedAllergic asthma 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 and Quantified0-470986.184 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease
details
Associated Disorders and Diseases
Disease References
Asthma
  1. Caldeira M, Perestrelo R, Barros AS, Bilelo MJ, Morete A, Camara JS, Rocha SM: Allergic asthma exhaled breath metabolome: a challenge for comprehensive two-dimensional gas chromatography. J Chromatogr A. 2012 Sep 7;1254:87-97. doi: 10.1016/j.chroma.2012.07.023. Epub 2012 Jul 16. [PubMed:22835687 ]
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. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
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. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004925
KNApSAcK IDC00011400
Chemspider ID9478
KEGG Compound IDC07287
BioCyc IDCPD-7969
BiGG IDNot Available
Wikipedia LinkSulcatone
METLIN IDNot Available
PubChem Compound9862
PDB IDNot Available
ChEBI ID16310
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .