Showing Compound Card for 2-Methyl-2-hepten-6-one (CDB000388)

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Record Information
Version1.0
Created at2020-03-19 00:34:25 UTC
Updated at2020-12-07 19:07:25 UTC
CannabisDB IDCDB000388
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Methyl-2-hepten-6-one
Description6-Methyl-5-hetpen-2-one or sulcatone, also known as methylheptenone, 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. Sulcatone is a very hydrophobic methylketone, practically insoluble in water, and relatively neutral. It exists as a clear, colorless liquid. Sulcatone can be found in all eukaryotes, ranging from yeast to plants to humans. Sulcatone has a musty, apple green-bean, and pear-like taste. and a citrus-like lemongrass odor. It is a volatile oil component of citronella oil, lemon-grass oil and palmarosa oil. Sulcatone is naturally found in bay leaf, blackberry fruit, sour cherries, cloves, ginger and lavender. In insects and animals, it has a role as an alarm or attractant pheromone. In fact, sulcatone is one of a number of mosquito attractants, especially for those species such as Aedes aegypti with the odor receptor gene Or4 (PMID: 25391959 ). Sulcatone is secreted by humans in their sweat and is a compound frequently found in human body odors (but in few other mammals). Sulcoatone is used as a pheromone by ferrets, european badgers, red foxes, treefrogs, bedbugs, wasps and butterflies. Sulcatone is one of several ketones found in Cannabis sativa (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight126.2
Monoisotopic Molecular Weight126.1045
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:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-67 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-a1a351553f2efdaaf3bc2015-03-01View Spectrum
GC-MS2-Methyl-2-hepten-6-one, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-52448d8f5e75dfce2601Spectrum
GC-MS2-Methyl-2-hepten-6-one, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-52448d8f5e75dfce2601Spectrum
Predicted GC-MS2-Methyl-2-hepten-6-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-2a4a7d0cf2baca776c97Spectrum
Predicted GC-MS2-Methyl-2-hepten-6-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2900000000-1c6462dfab5ba93de56a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-9800000000-3a5a239448b9074b63292015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9000000000-b4f774fa9c89ef7f85a52015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-77ea35597ceee3c16d4b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4900000000-223aa0397cf0652e45562015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-7fc0a9ab1c35aabebd1a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-9000000000-127501d70495320af54a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lu-9000000000-8fc1002b65f6845238582021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-795b6ce8a1b72433148f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-5900000000-8f58954cc0b9f482a4e02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-532dc780633705c5e2132021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-8f7fbaf286a4bd19c2932021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035915
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. McBride CS, Baier F, Omondi AB, Spitzer SA, Lutomiah J, Sang R, Ignell R, Vosshall LB: Evolution of mosquito preference for humans linked to an odorant receptor. Nature. 2014 Nov 13;515(7526):222-7. doi: 10.1038/nature13964. [PubMed:25391959 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]