BETA-CARYOPHYLLENE (CHEM005037)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2016-05-19 01:57:32 UTC
Update Date2026-05-14 19:59:52 UTC
Accession NumberCHEM005037
Identification
Common NameBETA-CARYOPHYLLENE
ClassSmall Molecule
DescriptionA beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(e)-beta-CaryophylleneChEBI
(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
(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, ChEBI
l-CaryophyllenePhytoBank
beta-CaryophellenePhytoBank
β-CaryophellenePhytoBank
Chemical FormulaC15H24
Average Molecular Mass204.357 g/mol
Monoisotopic Mass204.188 g/mol
CAS Registry Number87-44-5
IUPAC Name(1R,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Traditional Namecaryophyllene
SMILES[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C
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+/t13-,14-/m1/s1
InChI KeyNPNUFJAVOOONJE-GFUGXAQUSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-0006-9600000000-f461c075128fda03909dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2900000000-666e65f6b538d4a0eeeaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-de2a6b536bb38d3c2951Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3950000000-6dc317c917393691dfefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-6900000000-5f5ee8e9f24e0511e186Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d6c31402204fa765cbc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-48307d26c19d0c84ce74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2900000000-741197d2390e8d4bc104Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0980000000-9f708eefb54c5860f003Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-18da8cef0774773a4664Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-7930000000-0de14671750170215e53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9400000000-c0fc2f9446fefc882918Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9600000000-0eeaa207a8899311023dSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0036792
FooDB IDFDB097248
Phenol Explorer IDNot Available
KNApSAcK IDC00003110
BiGG IDNot Available
BioCyc IDCPD-8230
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCaryophyllene
Chemspider ID4444848
ChEBI ID10357
PubChem Compound ID5281515
Kegg Compound IDC09629
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12409018
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18296628
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18574142
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20015227
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20398787
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20433083
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21366052
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21425686
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21941920
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=27871898
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=30281175
12. Karim H, Kamel M, Mouna BT, Thouraya C, Brahim M: Essential oil composition of Hypericum triquetrifolium Turra. aerial parts. Ital J Biochem. 2007 Mar;56(1):40-6.
13. Luo J, Guo X, Feng Y: [Constituents analysis on volatile oil of Pogostemon cablin from different collection time cultivated in Hainan]. Zhong Yao Cai. 2002 Jan;25(1):21-3.
14. Luo J, Feng Y, Guo X, Li X: [GC-MS analysis of volatile oil of herba Pogostemonis collected from Gaoyao county]. Zhong Yao Cai. 1999 Jan;22(1):25-8.
15. Nascimento JC, Barbosa LC, Paula VF, David JM, Fontana R, Silva LA, Franca RS: Chemical composition and antimicrobial activity of essential oils of Ocimum canum Sims. and Ocimum selloi Benth. An Acad Bras Cienc. 2011 Sep;83(3):787-99.
16. Bhatia SP, Letizia CS, Api AM: Fragrance material review on beta-caryophyllene alcohol. Food Chem Toxicol. 2008 Nov;46 Suppl 11:S95-6. doi: 10.1016/j.fct.2008.06.030. Epub 2008 Jul 1.
17. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
18. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
19. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
20. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
21. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
22. The lipid handbook with CD-ROM
23. Wikipedia: http://en.wikipedia.org/wiki/(-)-beta-caryophyllene_synthase
24. Wikipedia: http://en.wikipedia.org/wiki/(+)-beta-caryophyllene_synthase
25. Wikipedia: http://en.wikipedia.org/wiki/(E)-2-epi-beta-caryophyllene_synthase
26. MetaCyc: beta-caryophyllene biosynthesis: http://metacyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-6275
27. UniProt I6RAQ6 : (-)-beta-caryophyllene synthase: http://www.uniprot.org/uniprot/I6RAQ6
28. UniProt J7LJN5 : Beta-caryophyllene synthase: http://www.uniprot.org/uniprot/J7LJN5
29. UniProt Q8SA63 : Beta-caryophyllene synthase: http://www.uniprot.org/uniprot/Q8SA63