Record Information
Version1.0
Creation date2010-04-08 22:12:01 UTC
Update date2018-05-29 01:21:26 UTC
Primary IDFDB015736
Secondary Accession Numbers
  • FDB015737
Chemical Information
FooDB Namebeta-Caryophyllene
DescriptionConstituent of clove, cinnamon, mint, eucalyptus, thyme, lemon balm and many other oils. The main source is the clove tree Eugenia caryophyllata. Flavouring agent. beta-Caryophyllene is found in many foods, some of which are hyssop, red bell pepper, pot marjoram, and caraway.
CAS Number87-44-5
Structure
Thumb
Synonyms
SynonymSource
(+)-beta-CaryophylleneHMDB
(-)-beta-CaryophylleneHMDB
(-)-CaryophylleneHMDB
(-)-trans-CaryophylleneHMDB
(e)-beta-CaryophyleneHMDB
(e)-CaryophylleneHMDB
b-CaryophylleneHMDB
beta-(e)-CaryophylleneHMDB
beta-CariofilleneHMDB
beta-CaryophilleneHMDB
beta-CaryophyllenHMDB
beta-trans-CaryophylleneHMDB
e-beta-CaryophylleneHMDB
TincturoidHMDB
trans-beta-CaryophylleneHMDB
trans-CaryophylleneHMDB
Caryophyllene, (r*,4Z,9S*)-(+-)-isomerMeSH
Caryophyllene, (R-(r*,4E,9S))-isomerMeSH
Caryophyllene, (S-(r*,4Z,9S*))-isomerMeSH
(e)-beta-CaryophylleneMeSH
Caryophyllene, (R-(r*,4Z,9S*))-isomerMeSH
Caryophyllene, (S-(r*,4E,9S*))-isomerMeSH
IsocaryophylleneMeSH
(-)-caryophyllenebiospider
(-)-trans-caryophyllenebiospider
(−)-trans-Caryophyllenebiospider
(e)-β-caryophylenebiospider
(E)-Caryophyllenebiospider
β-(e)-caryophyllenebiospider
β-cariofillenebiospider
β-caryophillenebiospider
β-caryophyllenbiospider
β-caryophyllenebiospider
β-caryophyllene, (-)biospider
β-trans-caryophyllenebiospider
+ &betabiospider
b-Humulene (obsol.)db_source
Caryophyllenedb_source
Caryophyllene ,&alphabiospider
Caryophyllene ,alpha + &betabiospider
Caryophyllene ,alpha + beta mixt.biospider
Caryophyllene (e)biospider
E-β-caryophyllenebiospider
FEMA 2252db_source
mixt.biospider
T-β-caryophyllenebiospider
Trans-β-caryophyllenebiospider
Trans-caryophyllenebiospider
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
Polarizability25.94 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H24
IUPAC name(4Z)-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
DescriptionThis compound belongs to the class of chemical entities known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
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 DescriptorsNot Available
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 PointBp9.7 118-119°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]21D -15 (c, 2.6 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09629
Pubchem Compound ID5281515
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJZM35-H:KGV69-V
EAFUS ID555
Dr. Duke IDTRANS-CARYOPHYLLENE|BETA-CARYOPHYLLENE|CARYOPHYLLENE
BIGG IDNot Available
KNApSAcK IDC00003110
HET IDNot Available
Flavornet ID87-44-5
GoodScent IDrw1060851
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
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti acne50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti edemicDUKE
anti feedantDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leishmanic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti onychyoticDUKE
anti proliferantDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti streptococcic33282 A substance that kills or slows the growth of bacteria.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
candidicideDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
gastroprotective55324 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
larvicideDUKE
mosquitocide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
termitifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.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
spice
  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
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
clove
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dry
  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.