Record Information
Version1.0
Creation date2010-04-08 22:11:19 UTC
Update date2018-05-28 19:19:13 UTC
Primary IDFDB014535
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(+)-Fenchone
DescriptionWidespread in plants, e.g. found in fennel (Foeniculum vulgare). Flavouring ingredient [CCD]
CAS Number7787-20-4
Structure
Thumb
Synonyms
SynonymSource
1,3,3-Trimethyl-2-norbornanoneChEBI
1,3,3-Trimethyl-2-norcamphanoneChEBI
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-oneChEBI
(1R,4S)-(+)-FenchoneHMDB
(1R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-oneHMDB
(1R,4S)-Fenchan-2-oneHMDB
(1R,4S)-FenchoneHMDB
L-alpha-FenchoneHMDB
L-FenchoneHMDB
Fenchone, (1S)-isomerHMDB
Fenchone, (+-)-isomerHMDB
Fenchone, (1R)-isomerHMDB
(+)-FenchoneKEGG
(1S,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-onemanual
(1S,4R)-Fenchan-2-onemanual
(1S,4R)-Fenchonemanual
D-1,3,3-Trimethyl-2-norbornanonemanual
D-1,3,3-Trimethyl-2-norcamphanonemanual
D-Fenchonemanual
FEMA 2479db_source
Predicted Properties
PropertyValueSource
Water Solubility0.88 g/LALOGPS
logP2.54ALOGPS
logP3.06ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.54 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16O
IUPAC name1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
InChI IdentifierInChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3
InChI KeyLHXDLQBQYFFVNW-UHFFFAOYSA-N
Isomeric SMILESCC1(C)C2CCC(C)(C2)C1=O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
Classification
Description belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Fenchane monoterpenoid
  • Bicyclic monoterpenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionOil with camphoraceous odourCCD
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointFp 5-6°DFC
Boiling PointBp 193.5°DFC
Experimental Water Solubility2.15 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]29D +63 . [a]21D +48 ( c, 0.2 in CCl4)CCD
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-39548fbec25228381f9bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-a6f20ad638918f01e975View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-39548fbec25228381f9bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-a6f20ad638918f01e975View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0043-9400000000-8a489af79633badeca62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-24a8ed13cef6845f9becView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-48ac2ef18d27307d28a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9200000000-a262db5efd11c7793ea7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-611d1944cb83d52bd473View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-aa8c9e54bea95cd3d999View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01c9-5900000000-7356fe255f32eabff21cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00lr-9000000000-0490bda5c76f7c0af3bdView in MoNA
ChemSpider ID13869
ChEMBL IDNot Available
KEGG Compound IDC09859
Pubchem Compound ID14525
Pubchem Substance IDNot Available
ChEBI ID165
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34985
CRC / DFC (Dictionary of Food Compounds) IDJRN54-N:JFM49-E
EAFUS ID1364
Dr. Duke IDD-FENCHONE|(+)-FENCHONE
BIGG IDNot Available
KNApSAcK IDC00011027
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1017711
SuperScent IDNot Available
Wikipedia IDFenchone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
camphor
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
thuja
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cedarleaf
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
earthy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.