Record Information
Version1.0
Creation date2010-04-08 22:12:01 UTC
Update date2018-05-29 01:21:23 UTC
Primary IDFDB015732
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCaryophyllene alpha-oxide
DescriptionConstituent of oil of cloves (Eugenia caryophyllata)and is) also in oils of Betula alba, Mentha piperita (peppermint) and others. Caryophyllene alpha-oxide is found in many foods, some of which are spearmint, cloves, ceylon cinnamon, and herbs and spices.
CAS Number1139-30-6
Structure
Thumb
Synonyms
SynonymSource
Caryophyllene a-oxideGenerator
Caryophyllene α-oxideGenerator
(-)-beta-Caryophyllene epoxideHMDB
(-)-EpoxydihydrocaryophylleneHMDB
beta-Caryophyllene epoxideHMDB
beta-Caryophyllene oxideHMDB
Caryophylene oxideHMDB
Caryophyllene epoxideHMDB
Caryophyllene oxydeHMDB
Caryophyllene oxideMeSH
(-)-β-caryophyllene epoxidebiospider
(-)-epoxydihydrocaryophyllenebiospider
β-caryophyllene epoxidebiospider
β-caryophyllene oxidebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.007 g/LALOGPS
logP3.49ALOGPS
logP3.62ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.21 m³·mol⁻¹ChemAxon
Polarizability26.42 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H24O
IUPAC name4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecane
InChI IdentifierInChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3
InChI KeyNVEQFIOZRFFVFW-UHFFFAOYSA-N
Isomeric SMILESCC12CCC3C(CC3(C)C)C(=C)CCC1O2
Average Molecular Weight220.3505
Monoisotopic Molecular Weight220.18271539
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
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 81.76%; H 10.98%; O 7.26%DFC
Melting PointMp 63.5-64°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -79.4 (c, 2.32 in CHCl3)DFC
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, Positivesplash10-03di-2920000000-d2a03a5c7a66db83cebaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-f8f0be1391f197a799e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-2490000000-fa2d7bb36e26ed264487View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9400000000-abbf14c22de1acb12c5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-f8f0be1391f197a799e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-2490000000-fa2d7bb36e26ed264487View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9400000000-abbf14c22de1acb12c5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-f8f0be1391f197a799e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-2490000000-fa2d7bb36e26ed264487View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9400000000-abbf14c22de1acb12c5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-0c846f045345079a830dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1190000000-c8390951524f03b71269View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdi-8930000000-6906b65254e00eb83985View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-0c846f045345079a830dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1190000000-c8390951524f03b71269View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdi-8930000000-6906b65254e00eb83985View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-0c846f045345079a830dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1190000000-c8390951524f03b71269View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdi-8930000000-6906b65254e00eb83985View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC16908
Pubchem Compound ID1742211
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDKGV62-O:KGV63-P
EAFUS ID560
Dr. Duke IDBETA-CARYOPHYLLENE-OXIDE|EPOXYCARYOPHYLLENE|CARYOPHYLLENEPOXIDE
BIGG IDNot Available
KNApSAcK IDC00012483
HET IDNot Available
Flavornet ID1139-30-6
GoodScent IDrw1023631
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
herb
  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
sweet
  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.
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
fresh
  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.
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.