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Showing Compound Fenchone (FDB014519)

Record Information
Version1.0
Creation date2010-04-08 22:11:19 UTC
Update date2019-11-26 03:10:16 UTC
Primary IDFDB014519
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFenchone
DescriptionFenchone is a natural organic compound classified as a monoterpene and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fenchone is used as a flavor in foods and in perfumery. Only 2 stereoisomers are possible: D-fenchone (enantiomer 1S,4R is dextrogyre (+)) and L-fenchone (enantiomer 1R,4S is levogyre (-)). Due to the small size of the cycle, the 2 other diastereoisomers (1S4S and 1R4R) are not possible. [Wikipedia]. Fenchone is found in many foods, some of which are ceylon cinnamon, sweet basil, saffron, and dill.
CAS Number1195-79-5
Structure
Thumb
MOLSDFPDBSMILESInChI
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)-isomerMeSH, HMDB
Fenchone, (+-)-isomerMeSH, HMDB
Fenchone, (1R)-isomerMeSH, HMDB
(+)-FenchoneKEGG
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one, 9CIdb_source
Fenchol (obsol.)db_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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00lr-9000000000-0490bda5c76f7c0af3bd2015-03-01View Spectrum
GC-MS(-)-Fenchone, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-39548fbec25228381f9bSpectrum
GC-MS(-)-Fenchone, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-a6f20ad638918f01e975Spectrum
GC-MS(-)-Fenchone, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-39548fbec25228381f9bSpectrum
GC-MS(-)-Fenchone, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-a6f20ad638918f01e975Spectrum
GC-MS(-)-Fenchone, non-derivatized, GC-MS Spectrumsplash10-00lr-9000000000-6be6cc8fad0feab50dc4Spectrum
Predicted GC-MS(-)-Fenchone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0043-9400000000-8a489af79633badeca62Spectrum
Predicted GC-MS(-)-Fenchone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-24a8ed13cef6845f9bec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-48ac2ef18d27307d28a42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9200000000-a262db5efd11c7793ea72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-611d1944cb83d52bd4732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-aa8c9e54bea95cd3d9992016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01c9-5900000000-7356fe255f32eabff21c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-2a5636c44361fc4733062021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-620886e230bbabe8a4ef2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-5900000000-b24f702346175a6b01002021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0043-9200000000-42f567566720679e24e52021-09-24View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID14525
Pubchem Substance IDNot Available
ChEBI ID4999
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJRN54-N:JRN54-N
EAFUS IDNot Available
Dr. Duke IDALPHA-FENCHONE|FENCHONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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 / Bioactivities
DescriptorIDDefinitionReference
Anti-Alzheimeran52217 An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.DUKE
Anti cholinesterase37733 An agent that inhibits acetylcholinesterase, increasing acetylcholine levels, and enhancing cholinergic transmission. Therapeutically, it's used to treat myasthenia gravis, glaucoma, and Alzheimer's disease, improving muscle strength, reducing eye pressure, and enhancing cognitive function.DUKE
CounterirritantAn agent that induces mild irritation or inflammation in one area to reduce discomfort and/or inflammation in another, often used to relieve pain, reduce swelling, and promote healing in conditions like arthritis, sprains, and strains.DUKE
Name48318 flavorDUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
SecretolyticAn agent that increases serous mucus production in the respiratory tract, aiding in clearing debris and excess mucus. Its therapeutic applications include relieving respiratory congestion and coughs, making it useful in managing conditions like bronchitis, asthma, and chronic obstructive pulmonary disease (COPD).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).