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Showing Compound (S)-alpha-Phellandrene (FDB013568)

Record Information
Version1.0
Creation date2010-04-08 22:10:47 UTC
Update date2020-09-17 15:31:25 UTC
Primary IDFDB013568
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-alpha-Phellandrene
Descriptionalpha-Phellandrene, also known as menthadiene, is one of two known Phellandrene isomers, alpha- and beta-, which are double-bonded. In α-phellandrene, both double bonds are endocyclic and in alpha-phellandrene, one of them is exocyclic. alpha-Phellandrene 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. alpha-Phellandrene is possibly neutral, insoluble in water, but miscible with ether. alpha-Phellandrene has a mint, spice, and turpentine taste. alpha-Phellandrene is found in highest concentrations in anises, common sages, and ceylon cinnamons and in lower concentrations in peppermints. alpha-Phellandrene has also been detected in dills, fennels, sweet basils, and tarragons. This could make alpha-phellandrene a potential biomarker for the consumption of these foods. The phellandrenes are used in fragrances because of their pleasing aromas.
CAS Number2243-33-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(4S)-p-Mentha-1(6),2-dieneChEBI
(5S)-5-Isopropyl-2-methylcyclohexa-1,3-dieneChEBI
(S)-(+)-alpha-PhellandreneChEBI
(S)-(+)-a-PhellandreneGenerator
(S)-(+)-Α-phellandreneGenerator
(S)-a-PhellandreneGenerator
(S)-Α-phellandreneGenerator
(+)-alpha-PhellandreneHMDB
(4S)-P-Mentha-1,5-dieneHMDB
(5S)-2-Methyl-5-(propan-2-yl)cyclohexa-1,3-dieneHMDB
D-alpha-PhellandreneHMDB
(+)-a-PhellandreneGenerator
(+)-Α-phellandreneGenerator
(4S)-p-Mentha-1,5-dienebiospider
(S)-(+)-α-phellandreneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP4.29ALOGPS
logP3.21ChemAxon
logS-3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.82 m³·mol⁻¹ChemAxon
Polarizability17.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16
IUPAC name(5S)-2-methyl-5-(propan-2-yl)cyclohexa-1,3-diene
InChI IdentifierInChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m0/s1
InChI KeyOGLDWXZKYODSOB-JTQLQIEISA-N
Isomeric SMILES[H][C@]1(CC=C(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
  • 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 DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting PointNot Available
Boiling PointBp 175-176°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +49.1DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-alpha-Phellandrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-0fe1966be3faee829decSpectrum
Predicted GC-MS(S)-alpha-Phellandrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-84435206059b57657bff2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9600000000-f16481e876627d7d4bdf2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-6993cdda47b7e020b82d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-380abae33f914a4d40012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-099421ca3a157c7e1c712016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-7900000000-58a61cb646aec74939282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000m-9500000000-57eb4e7b936ea365be202021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9000000000-7265bcee351c38f0f79c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ou-9000000000-0d460f957e928551b42c2021-09-24View 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-a013b4ae27f975ab56212021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-9000000000-5a30982006f09d04cfc82021-09-24View Spectrum
NMRNot Available
ChemSpider ID391432
ChEMBL IDNot Available
KEGG Compound IDC11391
Pubchem Compound ID443160
Pubchem Substance IDNot Available
ChEBI ID367
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34970
CRC / DFC (Dictionary of Food Compounds) IDJTB20-G:JFH66-I
EAFUS IDNot Available
Dr. Duke ID(+)-ALPHA-PHELLANDRENE|D-ALPHA-PHELLANDRENE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID2243-33-6
GoodScent IDrw1374391
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
Flavours
FlavorCitations
dill
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. 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 ReferenceNot Available