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(-)-beta-Phellandrene (FDB021860)

Record Information
Version1.0
Creation date2011-06-09 23:26:07 UTC
Update date2020-09-17 15:31:25 UTC
Primary IDFDB021860
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-beta-Phellandrene
DescriptionBeta-Phellandrene, also known 2-p-menthadiene, is one of two known Phellandrene isomers, α- and β-, which are double-bonded. In α-phellandrene, both double bonds are endocyclic and in β-phellandrene, one of them is exocyclic. It belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Plants biosynthesize phellandrene through geranyl pyrophosphate (GPP) in the mevalonate pathway (MVA, PMID: 17467679). The MVA pathway yields the precursors dimethylallyl pyrophosphate and isopentenyl pyrophosphate which combine to produce GPP. This resultant monoterpene undergoes cyclization to form a menthyl cationic species. A hydride shift then forms an allylic carbocation followed by an elimination reaction that occurs at one of two positions, yielding either alpha-phellandrene or beta-phellandrene. Beta-phellandrene colorless to pale yellow clear liquid with a minty, terpenic odor ( http://www.thegoodscentscompany.com/data/rw1103551.html#tophyp). It is found in allspice and is widely distributed in essential oils from various plant families including Angelica, Eucalyptus, Lavandula, Mentha, Pinus species, water fennel, Canada balsam and Cannibis. It is also used as a perfuming agent or fragrance ingredient in cosmetics. Beta-phellandrene is found in, or is added to many foods including dairy products, confectionery, frozen dairy treats, soups and sauces. It has also found use as a natural pesticide. It has recently been found to induce DNA damage at high doses (2850 mg/kg) (PMID: 28668705).
CAS Number6153-17-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP3.98ALOGPS
logP3.26ChemAxon
logS-3.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.75 m³·mol⁻¹ChemAxon
Polarizability17.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16
IUPAC name(6S)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene
InChI IdentifierInChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m0/s1
InChI KeyLFJQCDVYDGGFCH-JTQLQIEISA-N
Isomeric SMILES[H][C@]1(CCC(=C)C=C1)C(C)C
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
Classification
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionOilDFC
Mass CompositionC 88.16%; H 11.84%DFC
Melting PointNot Available
Boiling PointBp 172-174°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -74.4DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4826DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-e24239e4ab38fb2abd262015-03-01View Spectrum
Predicted GC-MS(-)-beta-Phellandrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-713c1b25c4555f3e77f2Spectrum
Predicted GC-MS(-)-beta-Phellandrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-f7f288db31b30052203d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9600000000-48905d36448ddbdd3f792016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-344480f8a40ee3d9f0982016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-2950ad058f77d7bc9f762016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-2146d0245e5c9841d77b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-7900000000-7c7a8d3355c299f4c5472016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-240ec64fc20c6bf382ba2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-e2fc12c61b510c2b91a02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000m-9500000000-d031cd9010fdf4f6493d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9000000000-de55c3652434eddf0c782021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-9000000000-bc41a7ccf7c0983ef3532021-09-24View Spectrum
NMR
TypeDescriptionView
ChemSpider ID391433
ChEMBL IDNot Available
KEGG Compound IDC11392
Pubchem Compound ID443161
Pubchem Substance IDNot Available
ChEBI ID129
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41633
CRC / DFC (Dictionary of Food Compounds) IDJXJ81-P:JSV16-Y
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00010873
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhellandrene
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
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.