Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:12:01 UTC
Update date2018-05-29 01:21:27 UTC
Primary IDFDB015737
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namegamma-Caryophyllene
DescriptionWidespread in plants (Jasminum, Origanum and Pimpinella subspecies). gamma-Caryophyllene is found in many foods, some of which are herbs and spices, ceylon cinnamon, cumin, and common sage.
CAS Number87-44-5
Structure
Thumb
Synonyms
SynonymSource
(e)-beta-CaryophylleneChEBI
CaryophylleneChEBI
trans-(1R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-eneChEBI
trans-CaryophylleneChEBI
(-)-beta-CaryophylleneKegg
(e)-b-CaryophylleneGenerator
(e)-Β-caryophylleneGenerator
(-)-b-CaryophylleneGenerator
(-)-Β-caryophylleneGenerator
b-CaryophylleneGenerator
Β-caryophylleneGenerator
Caryophyllene, (S-(r*,4Z,9S*))-isomerHMDB
Caryophyllene, (R-(r*,4E,9S))-isomerHMDB
Caryophyllene, (r*,4Z,9S*)-(+-)-isomerHMDB
Caryophyllene, (R-(r*,4Z,9S*))-isomerHMDB
Caryophyllene, (S-(r*,4E,9S*))-isomerHMDB
(-)-(e)-CaryophylleneHMDB
(-)-e-CaryophylleneHMDB
(-)-CaryophylleneHMDB
(-)-trans-CaryophylleneHMDB
(e)-CaryophylleneHMDB
Caryophyllene bHMDB
NSC 11906HMDB
trans-Β-caryophylleneHMDB
trans-beta-CaryophylleneHMDB
Β-caryophyllenHMDB
beta-CaryophyllenHMDB
beta-CaryophylleneHMDB
(+)-beta-CaryophylleneHMDB
(e)-beta-CaryophyleneHMDB
(z)-β-caryophyllenebiospider
(z)-caryophyllenebiospider
β-cis-caryophyllenebiospider
beta-(e)-CaryophylleneHMDB
beta-CariofilleneHMDB
beta-CaryophilleneHMDB
beta-trans-CaryophylleneHMDB
Caryophyllene ,alpha + beta mixtbiospider
caryophyllene, (R-(R*,4E,9S))-isomerbiospider
e-beta-CaryophylleneHMDB
g-Caryophyllenedb_source
Isocaryophyllenedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP5.35ALOGPS
logP4.52ChemAxon
logS-4.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity67.45 m³·mol⁻¹ChemAxon
Polarizability25.65 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H24
IUPAC name(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
InChI IdentifierInChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-
InChI KeyNPNUFJAVOOONJE-WDZFZDKYSA-N
Isomeric SMILESC\C1=C\CCC(=C)C2CC(C)(C)C2CC1
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
Classification
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Caryophyllane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting Point< 25 oC
Boiling PointBp14.5 125°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]24D -27DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2900000000-666e65f6b538d4a0eeeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-de2a6b536bb38d3c2951View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3950000000-6dc317c917393691dfefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-6900000000-5f5ee8e9f24e0511e186View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d6c31402204fa765cbc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-48307d26c19d0c84ce74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2900000000-741197d2390e8d4bc104View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9600000000-0eeaa207a8899311023dView in MoNA
ChemSpider ID4479685
ChEMBL IDNot Available
KEGG Compound IDC09629
Pubchem Compound ID5322111
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36792
CRC / DFC (Dictionary of Food Compounds) IDJZM35-H:KGV70-P
EAFUS IDNot Available
Dr. Duke IDCIS-CARYOPHYLLENE|GAMMA-CARYOPHYLLENE|ISOCARYOPHYLLENE
BIGG IDNot Available
KNApSAcK IDC00012474
HET IDNot Available
Flavornet ID118-65-0
GoodScent IDrw1382561
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
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
wood
  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.
spicy
  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.