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Camphene (FDB009065)

Record Information
Version1.0
Creation date2010-04-08 22:08:24 UTC
Update date2019-11-26 03:03:24 UTC
Primary IDFDB009065
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCamphene
DescriptionCamphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Camphene is a camphor, fir needle, and herbal tasting compound and can be found in a number of food items such as cardamom, yellow bell pepper, common thyme, and coriander, which makes camphene a potential biomarker for the consumption of these food products. Camphene can be found primarily in feces and saliva. Camphene exists in all eukaryotes, ranging from yeast to humans. Camphene is a bicyclic monoterpene. It is nearly insoluble in water, but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and as a food additive for flavoring. Its mid-19th century use as a fuel for lamps was limited by its explosiveness .
CAS Number79-92-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.062 g/LALOGPS
logP4.56ALOGPS
logP2.86ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.65 m³·mol⁻¹ChemAxon
Polarizability16.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16
IUPAC name2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane
InChI IdentifierInChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3
InChI KeyCRPUJAZIXJMDBK-UHFFFAOYSA-N
Isomeric SMILESCC1(C)C2CCC(C2)C1=C
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
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
  • Bicyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point51.2 oC
Boiling PointNot Available
Experimental Water Solubility0.0046 mg/mL at 25 oCCHEMICALS INSPECTION AND TESTING INSTITU (1992)
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)splash10-002f-9200000000-14687f2522a9e8543e302015-03-01View Spectrum
GC-MSCamphene, non-derivatized, GC-MS Spectrumsplash10-0006-9200000000-16357f038546002c5eb6Spectrum
GC-MSCamphene, non-derivatized, GC-MS Spectrumsplash10-0596-9600000000-d86709e82362aaadd573Spectrum
GC-MSCamphene, non-derivatized, GC-MS Spectrumsplash10-0006-9200000000-16357f038546002c5eb6Spectrum
GC-MSCamphene, non-derivatized, GC-MS Spectrumsplash10-0596-9600000000-d86709e82362aaadd573Spectrum
GC-MSCamphene, non-derivatized, GC-MS Spectrumsplash10-0006-9200000000-b7f3e7fc70b75884c8e1Spectrum
Predicted GC-MSCamphene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0avl-9600000000-6c7bdfedc9e1bb60d855Spectrum
Predicted GC-MSCamphene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-196b02102f0ebf09b5342016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-c52b7cd8940e2fb05c542016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-6f9543516068b727c1562016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-cce5a3a8054b82bf623f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-cce5a3a8054b82bf623f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-3b379a5acd27d5e4086c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-0900000000-5f08b0d51d8859e573d82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014s-9300000000-10513da20f6a7537fd9b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06fu-9500000000-5bf329b2ba88ea32211b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0693-9300000000-cc0f0b0ffa4549f4dcfc2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC06076
Pubchem Compound ID6616
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID490
Dr. Duke IDCAMPHENE
BIGG IDNot Available
KNApSAcK IDC00003029
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID79-92-5
GoodScent IDrw1006291
SuperScent IDNot Available
Wikipedia IDNot Available
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
allelopathicDUKE
anti lithicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
hypocholesterolemicDUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
spasmogenicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
camphor
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
woody
  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.
fir needle
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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.