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Showing Compound gamma-Elemene (FDB004787)

Record Information
Version1.0
Creation date2010-04-08 22:06:24 UTC
Update date2020-09-17 15:32:35 UTC
Primary IDFDB004787
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namegamma-Elemene
DescriptionGamma-Elemene, also known as g-elemene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. More formally, gamma-elemene is a cyclohexane substituted at positions 1, 1, 2, and 4 by methyl, vinyl, isopropenyl and isopropylidene groups, respectively. There are four known elemene isomers including α-, β-, γ-, and δ-elemene. The elemenes contribute to the floral aromas of some plants and are used as pheromones by some insects. Gamma-elemene is found in many essential plant oils including wormwood leaf oil, peppermint oil, pepper tree leaf oil, parsley leaf oil, orange peel oil, lime oil, juniper berry oil, hinoki leaf oil, angelica root oil, and angelica seed oil. Gamma-elemene has been shown to exhibit good insecticidal activity against the crop pest Spodoptera litura (tobacco cutworm or cotton leafworm) and could be useful as an eco-friendly biopesticide (PMID:28634795).
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0091 g/LALOGPS
logP5.09ALOGPS
logP4.64ChemAxon
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.03 m³·mol⁻¹ChemAxon
Polarizability25.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H24
IUPAC name(1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane
InChI IdentifierInChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,14H,1,4,8-10H2,2-3,5-6H3/t14-,15+/m0/s1
InChI KeyBQSLMQNYHVFRDT-LSDHHAIUSA-N
Isomeric SMILESCC(C)=C1CC[C@@](C)(C=C)[C@@H](C1)C(C)=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
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSgamma-Elemene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0019-4900000000-fb790115baaf4a3d1616Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1890000000-450e146224ccff06d6172016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07br-3910000000-61daee527832bc1811302016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9300000000-84044dadf41caec7632f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6bfd709831d5599e9c1e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-b951c20dccfd334852ad2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1900000000-9c9cef0e084401e873e92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-022i-0900000000-b8727734b8bc280cd8072021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9710000000-8f184d721121df33f4dc2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-069u-9300000000-dc6712d7b870be6f2b3a2021-10-21View 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, Negativesplash10-0zg0-0940000000-75fae33c5b380ac995912021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6432312
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 IDGAMMA-ELEMENE
BIGG IDNot Available
KNApSAcK IDC00012012
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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
FlavoursNot Available
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).