Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:06:51 UTC
Update date2018-05-28 23:14:47 UTC
Primary IDFDB005805
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLongifolene
DescriptionLongifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts .
CAS Number475-20-7
Structure
Thumb
Synonyms
SynonymSource
(+)-longifolenbiospider
(+)-longifolenebiospider
(+)-longofolenebiospider
α-longifolenebiospider
1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-biospider
1,4-Methanoazulene, Junipenbiospider
4,8,8-trimethyl-9-methylidenedecahydro-1,4-methanoazulenebiospider
D-longifolenebiospider
Junipenbiospider
Junipenebiospider
Kuromatsuenbiospider
Kuromatsuenebiospider
Longifolenbiospider
Longifolenebiospider
Longifolene (=junipene)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.0013 g/LALOGPS
logP4.65ALOGPS
logP4.16ChemAxon
logS-5.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity64.62 m³·mol⁻¹ChemAxon
Polarizability25.42 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H24
IUPAC name3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0²,⁹]undecane
InChI IdentifierInChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3
InChI KeyPDSNLYSELAIEBU-UHFFFAOYSA-N
Isomeric SMILESCC12CCCC(C)(C)C3C(CCC13)C2=C
Average Molecular Weight204.357
Monoisotopic Molecular Weight204.187800773
Classification
ClassificationNot classified
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointBoiling Pt : 258 oC
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, Positivesplash10-01s9-2900000000-035dbcf027d0dfba677bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-8be5b82f1970df5d0fbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1390000000-5b0723496471550d90fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00n0-8900000000-96000d2a703ee43023eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d8dbe2f117875c63d9b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-b23a97fc2ece08b93c5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1900000000-023300ca2a969c85df78View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4l-9800000000-39919bcbac1cbe903234View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09699
Pubchem Compound ID289151
Pubchem Substance IDNot Available
ChEBI ID6530
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDKMC00-T:KMC00-T
EAFUS IDNot Available
Dr. Duke IDLONGIFOLENE
BIGG IDNot Available
KNApSAcK IDC00003162
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1020031
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
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.
rose
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medical
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fir needle
  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).