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Showing Compound Longifolene (FDB005805)

Record Information
Version1.0
Creation date2010-04-08 22:06:51 UTC
Update date2019-11-26 03:00:46 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
MOLSDFPDBSMILESInChI
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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
  • Longifolane or isolongifolane 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
OntologyNo ontology term
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4l-9800000000-39919bcbac1cbe9032342015-03-01View Spectrum
Predicted GC-MSLongifolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01s9-2900000000-035dbcf027d0dfba677bSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-8be5b82f1970df5d0fba2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1390000000-5b0723496471550d90fb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00n0-8900000000-96000d2a703ee43023ea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d8dbe2f117875c63d9b72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-b23a97fc2ece08b93c5d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1900000000-023300ca2a969c85df782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-957001643af9742967792021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-4940000000-08e8b30216bee8b9d0b72021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-6900000000-2057ea9054379c9d846d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-6efb1ac8bbe4b57b1ab92021-10-21View Spectrum
NMR
TypeDescriptionView
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
Food Biomarker OntologyNot Available
VMH 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).