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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:58:08 UTC
Update Date2018-05-20 00:29:22 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
Thumb
Synonyms
ValueSource
(e)-beta-CaryophylleneChEBI
CaryophylleneChEBI
trans-(1R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-eneChEBI
trans-CaryophylleneChEBI
(e)-b-CaryophylleneGenerator
(e)-β-caryophylleneGenerator
b-CaryophylleneGenerator
β-caryophylleneGenerator
Caryophyllene, (S-(r*,4Z,9S*))-isomerMeSH
Caryophyllene, (R-(r*,4E,9S))-isomerMeSH
Caryophyllene, (r*,4Z,9S*)-(+-)-isomerMeSH
Caryophyllene, (R-(r*,4Z,9S*))-isomerMeSH
Caryophyllene, (S-(r*,4E,9S*))-isomerMeSH
(-)-(E)-CaryophylleneCAS
(-)-E-CaryophylleneCAS
(-)-CaryophylleneCAS
(-)-trans-CaryophylleneCAS
(-)-β-CaryophylleneCAS
(-)-beta-CaryophylleneCAS
(E)-CaryophylleneCAS
Caryophyllene BCAS
NSC 11906CAS
trans-β-CaryophylleneCAS
trans-beta-CaryophylleneCAS
β-CaryophyllenCAS
beta-CaryophyllenCAS
beta-CaryophylleneHMDB
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
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 RuleYesChemAxon
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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Children (1-13 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
SalivaDetected but not Quantified Children (1-13 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
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 ]
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003110
Chemspider IDNot Available
KEGG Compound IDC09629
BioCyc IDCPD-8230
BiGG IDNot Available
Wikipedia LinkCaryophyllene
METLIN IDNot Available
PubChem Compound5281515
PDB IDNot Available
ChEBI ID10357
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]