Showing Compound Card for beta-Phellandrene (CDB000200)

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Record Information
Version1.0
Created at2020-03-18 23:28:29 UTC
Updated at2020-12-07 19:07:15 UTC
CannabisDB IDCDB000200
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namebeta-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 ( Ref:DOI ). 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. Beta-phellandrene is one of the monoterpenes found in cannabis plants (PMID: 6991645 ). 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 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-p-Mentha-1(7),2-dieneChEBI
(S)-3-Isopropyl-6-methylenecyclohexeneChEBI
(+)-b-PhellandreneGenerator
(+)-Β-phellandreneGenerator
(-)-P-Mentha-1(7),2-dieneHMDB
(3R)-3-Isopropyl-6-methylenecyclohexeneHMDB
(4R)-P-Mentha-1(7),2-dieneHMDB
(6R)-3-Methylidene-6-(propan-2-yl)cyclohex-1-eneHMDB
(R)-3-Isopropyl-6-methylenecyclohexeneHMDB
L-beta-PhellandreneHMDB
(-)-b-PhellandreneGenerator
(-)-Β-phellandreneGenerator
Chemical FormulaC10H16
Average Molecular Weight136.23
Monoisotopic Molecular Weight136.1252
IUPAC Name(6S)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene
Traditional Name(+)-β-phellandrene
CAS Registry Number6153-16-8
SMILES
CC(C)[C@@H]1CCC(=C)C=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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

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Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-e24239e4ab38fb2abd262015-03-01View Spectrum
Predicted GC-MSbeta-Phellandrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-713c1b25c4555f3e77f2Spectrum
Predicted GC-MSbeta-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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0041634
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021861
KNApSAcK IDC00010873
Chemspider ID390916
KEGG Compound IDC09877
BioCyc IDCPD-8769
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442484
PDB IDNot Available
ChEBI ID53
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Cheng Z, Jiang J, Yang X, Chu H, Jin M, Li Y, Tao X, Wang S, Huang Y, Shang L, Wu S, Hao W, Wei X: The research of genetic toxicity of beta-phellandrene. Environ Toxicol Pharmacol. 2017 Sep;54:28-33. doi: 10.1016/j.etap.2017.06.011. Epub 2017 Jun 20. [PubMed:28668705 ]
  3. Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. [PubMed:17467679 ]