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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:58:08 UTC
Update Date2022-03-07 02:55:03 UTC
HMDB IDHMDB0036792
Secondary Accession Numbers
  • HMDB0061842
  • HMDB36792
  • HMDB61842
Metabolite Identification
Common Namebeta-Caryophyllene
Descriptionbeta-Caryophyllene, also known as caryophyllene or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils including that of Syzygium aromaticum (cloves), Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. beta-Caryophyllene is notable for having both a cyclobutane ring and a trans-double bond in a nine-membered ring, both rarities in nature (Wikipedia ). beta-Caryophyllene is a sweet and dry tasting compound that can be found in a number of food items such as allspice, fig, pot marjoram, and roman camomile, which makes beta-caryophyllene a potential biomarker for the consumption of these food products. beta-Caryophyllene can be found in feces and saliva.
Structure
Data?1563862928
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 Weight204.357
Monoisotopic Molecular Weight204.187800773
IUPAC Name(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Traditional Namecaryophyllene
CAS Registry Number87-44-5
SMILES
[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C
InChI Identifier
InChI=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
Ontology
Physiological effect
Disposition
Source
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point256.00 to 259.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.300The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.0931661259
DarkChem[M-H]-147.16631661259
DeepCCS[M-2H]-186.2230932474
DeepCCS[M+Na]+161.29230932474
AllCCS[M+H]+147.332859911
AllCCS[M+H-H2O]+143.232859911
AllCCS[M+NH4]+151.032859911
AllCCS[M+Na]+152.132859911
AllCCS[M-H]-156.032859911
AllCCS[M+Na-2H]-156.432859911
AllCCS[M+HCOO]-157.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-Caryophyllene[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C1644.0Standard polar33892256
beta-Caryophyllene[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C1447.0Standard non polar33892256
beta-Caryophyllene[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C1442.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - beta-Caryophyllene GC-EI-Q (Non-derivatized)splash10-0006-9600000000-f461c075128fda03909d2020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Caryophyllene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2900000000-666e65f6b538d4a0eeea2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Caryophyllene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9600000000-0eeaa207a8899311023d2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 10V, Positive-QTOFsplash10-0a4i-0290000000-de2a6b536bb38d3c29512016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 20V, Positive-QTOFsplash10-0a4i-3950000000-6dc317c917393691dfef2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 40V, Positive-QTOFsplash10-0f7a-6900000000-5f5ee8e9f24e0511e1862016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 10V, Negative-QTOFsplash10-0udi-0090000000-d6c31402204fa765cbc02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 20V, Negative-QTOFsplash10-0udi-0290000000-48307d26c19d0c84ce742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 40V, Negative-QTOFsplash10-002r-2900000000-741197d2390e8d4bc1042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 10V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 20V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 40V, Negative-QTOFsplash10-0udi-0980000000-9f708eefb54c5860f0032021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 10V, Positive-QTOFsplash10-0a4i-0190000000-18da8cef0774773a46642021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 20V, Positive-QTOFsplash10-0a4j-7930000000-0de14671750170215e532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene 40V, Positive-QTOFsplash10-0a4m-9400000000-c0fc2f9446fefc8829182021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB097248
KNApSAcK IDC00003110
Chemspider ID4444848
KEGG Compound IDC09629
BioCyc IDCPD-8230
BiGG IDNot Available
Wikipedia LinkCaryophyllene
METLIN IDNot Available
PubChem Compound5281515
PDB IDNot Available
ChEBI ID10357
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1060851
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:21969960 ]
  2. 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. [PubMed:17511353 ]
  3. 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. [PubMed:12583236 ]
  4. 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. [PubMed:12575058 ]
  5. 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. [PubMed:18640216 ]
  6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  7. 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. [PubMed:16902246 ]
  8. 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. [PubMed:17374880 ]
  9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  10. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  12. Wikipedia [Link]
  13. Wikipedia [Link]
  14. Wikipedia [Link]
  15. MetaCyc: beta-caryophyllene biosynthesis [Link]
  16. UniProt I6RAQ6 : (-)-beta-caryophyllene synthase [Link]
  17. UniProt J7LJN5 : Beta-caryophyllene synthase [Link]
  18. UniProt Q8SA63 : Beta-caryophyllene synthase [Link]