Record Information
Version1.0
Creation date2010-04-08 22:06:00 UTC
Update date2018-05-29 00:39:08 UTC
Primary IDFDB003904
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Cedrene
DescriptionAlpha-cedrene, also known as (-)-α-cedrene or beta-cedrene, is a member of the class of compounds known as cedrane and isocedrane sesquiterpenoids. Cedrane and isocedrane sesquiterpenoids are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Thus, alpha-cedrene is considered to be an isoprenoid lipid molecule. Alpha-cedrene is a sweet, cedar, and fresh tasting compound and can be found in a number of food items such as tarragon, peppermint, wild celery, and common sage, which makes alpha-cedrene a potential biomarker for the consumption of these food products. Alpha-cedrene can be found primarily in urine.
CAS Number469-61-4
Structure
Thumb
Synonyms
SynonymSource
(-)-alpha-CedreneChEBI
(1S,2R,5S,7S)-2,6,6,8-Tetramethyltricyclo[5.3.1.0(1,5)]undec-8-eneChEBI
[3R-(3alpha,3Abeta,7beta,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazuleneChEBI
(-)-a-CedreneGenerator
(-)-Α-cedreneGenerator
[3R-(3a,3Abeta,7b,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazuleneGenerator
[3R-(3Α,3abeta,7β,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazuleneGenerator
a-CedreneGenerator
Α-cedreneGenerator
alpha-CedreneChEBI
beta-CedreneMeSH
CedroneMeSH
CedreneMeSH
α-Cedrenebiospider
Cedr-8-enebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP5.18ALOGPS
logP4.1ChemAxon
logS-5.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.69 m³·mol⁻¹ChemAxon
Polarizability25.72 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H24
IUPAC name(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0¹,⁵]undec-8-ene
InChI IdentifierInChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1
InChI KeyIRAQOCYXUMOFCW-OSFYFWSMSA-N
Isomeric SMILES[H][C@@]12CC[C@@H](C)[C@]11C[C@@H](C(C)=CC1)C2(C)C
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
Classification
Description belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentCedrane and isocedrane sesquiterpenoids
Alternative Parents
Substituents
  • Cedrane sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
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, Positivesplash10-03g1-1900000000-d9586d99c9949bf8088bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-cd7b7bd3ccd75e24c49bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0690000000-5c3400f19be2d725de04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9i-9800000000-6baec4093195d46de24aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6589dee75f8602eecab5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-1b2a943b4a7f32ee7b6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-1920000000-80c16a78fccc89798b3dView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09630
Pubchem Compound ID6431015
Pubchem Substance IDNot Available
ChEBI ID10216
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJPR59-Y:JJF32-N
EAFUS IDNot Available
Dr. Duke IDALPHA-CEDRENE|CEDRENE
BIGG IDNot Available
KNApSAcK IDC00003111
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1032351
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
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
irritantDUKE
perfume48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cedar
  1. 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.
fresh
  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.