Back to Compounds

Showing Compound Camphene (FDB009065)

Record Information
Version1.0
Creation date2010-04-08 22:08:24 UTC
Update date2025-11-18 23:15:02 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
2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptaneChEBI
2,2-Dimethyl-3-methylenenorbornaneChEBI
3,3-Dimethyl-2-methylenenorbornaneChEBI
3,3-Dimethyl-2-methylenenorcamphaneChEBI
CompheneChEBI
3,3-Dimethyl-2-methylidenebicyclo[2.2.1]heptaneHMDB
(1)-2,2-Dimethyl-3-methylenebicyclo(2.2.1)heptanebiospider
(1S)-2,2-Dimethyl-3-methylenebicyclo(2.2.1)heptanebiospider
2, 2-Dimethyl-3-methylenenorbornanebiospider
2,2-Dimethyl-3-methylenebicyclo(2.2.1)heptanebiospider
2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptanebiospider
3, 3-Dimethyl-2-methylenenorbornanebiospider
3, 3-Dimethyl-2-methylenenorcamphanebiospider
3,3-Dimethyl-2-methylenenorcamphenebiospider
Bicyclo(2.2.1)heptane, 2,2-dimethyl-3-methylene-biospider
Bicyclo(2.2.1)heptane, 2,2-dimethyl-3-methylene-, (1S,4R)-biospider
Bicyclo(2.2.1)heptane, 2,2-dimethyl-3-methylene-, (1S)-biospider
Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-biospider
Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-, (1R)-biospider
Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-, (1S)-biospider
Camphene (2,2-dimethyl-3-methylene-norbornane)biospider
L-camphenebiospider
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 ID6364
ChEMBL IDCHEMBL2268550
KEGG Compound IDC06076
Pubchem Compound ID6616
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0059839
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
AllelopathicBiochemicals that inhibit growth, survival, or reproduction in other organisms, with potential therapeutic applications in weed control, antimicrobial, and anticancer treatments, and key medical uses in developing novel pesticides, antibiotics, and chemotherapeutics.DUKE
Anti-lithicAn agent that prevents the formation of calculi (kidney stones) or promotes their dissolution, playing a key role in urology. Its therapeutic applications include managing kidney stone disease, nephrolithiasis, and urinary tract disorders, helping to alleviate pain and prevent complications.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Expectorant52217 An agent that thins and loosens mucus, making it easier to cough up, reducing congestion. It aids in clearing respiratory tract secretions, commonly used to relieve coughs, colds, and bronchitis, promoting easier breathing and soothing irritated airways.DUKE
Name48318 flavorDUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
SpasmogenicAn agent that induces spasms, causing sudden involuntary muscular contractions. It plays a biological role in stimulating muscle activity. Therapeutically, it has applications in diagnosing and treating muscle disorders. Key medical uses include assessing muscle function and treating conditions like muscle atrophy, with potential applications in physical therapy and rehabilitation.DUKE
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.