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Showing Compound Perillene (FDB007821)

Record Information
Version1.0
Creation date2010-04-08 22:07:47 UTC
Update date2020-09-17 15:32:29 UTC
Primary IDFDB007821
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePerillene
DescriptionPerillene, also known as perillen, belongs to the class of organic compounds known as monoterpenes. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Perillene also belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Perillene is a neutral, hydrophobic molecule that is insoluble in water. Perillene exists as a clear, colorless oil and has a woody, flowery, citrus aroma or taste. Perillene has been found in several plants and spices including ginger and oregano. It has also been found in the essential oils of other plants, such as Perilla ocimoides (PMID: 17269047), Kenyan Valencia (Citrus sinensis), Australian finger lime (Citrus australasica) peel oil, Neroli (Citrus aurantium) (PMID: 30723488) and Boswellia sacra (PMID: 18830149).
CAS Number539-52-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP3.78ALOGPS
logP3.29ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.42 m³·mol⁻¹ChemAxon
Polarizability18.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H14O
IUPAC name3-(4-methylpent-3-en-1-yl)furan
InChI IdentifierInChI=1S/C10H14O/c1-9(2)4-3-5-10-6-7-11-8-10/h4,6-8H,3,5H2,1-2H3
InChI KeyXNGKCOFXDHYSGR-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCCC1=COC=C1
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
Classification
Description Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassHeteroaromatic compounds
Sub ClassNot Available
Direct ParentHeteroaromatic compounds
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPerillene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-9200000000-f0341154e4be5fa2573fSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-6dcea2710a0949e79b782016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-8900000000-f29bf4a3afaf73292dc02016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9100000000-3a6d857807b0f470e15a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-30f53f9dce61f78cbbdc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-3d680fad94f20130b98a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-3900000000-0c611115b7c5f678041f2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPERILLENE|PERILLEN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID539-52-6
GoodScent IDrw1531331
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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).