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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:54:18 UTC
Update Date2022-03-07 02:54:18 UTC
HMDB IDHMDB0034970
Secondary Accession Numbers
  • HMDB34970
Metabolite Identification
Common Name(S)-alpha-Phellandrene
Description(S)-alpha-Phellandrene is found in ceylan cinnamon. (S)-alpha-Phellandrene is a flavouring agent. (S)-alpha-Phellandrene is a constituent of many essential oils including bitter fennel, elemi and ginger-grass oils. Oil of Ridolfia segetum is a major source (85%).Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia
Structure
Data?1563862644
Synonyms
ValueSource
(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
Chemical FormulaC10H16
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
IUPAC Name(5S)-2-methyl-5-(propan-2-yl)cyclohexa-1,3-diene
Traditional Name(+)-α-phellandrene
CAS Registry Number2243-33-6
SMILES
[H][C@]1(CC=C(C)C=C1)C(C)C
InChI Identifier
InChI=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
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
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point171.00 to 172.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2.86 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.432 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.74931661259
DarkChem[M-H]-130.07631661259
DeepCCS[M+H]+138.43230932474
DeepCCS[M-H]-136.03630932474
DeepCCS[M-2H]-170.60130932474
DeepCCS[M+Na]+144.82130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-alpha-Phellandrene[H][C@]1(CC=C(C)C=C1)C(C)C1130.6Standard polar33892256
(S)-alpha-Phellandrene[H][C@]1(CC=C(C)C=C1)C(C)C982.5Standard non polar33892256
(S)-alpha-Phellandrene[H][C@]1(CC=C(C)C=C1)C(C)C1011.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-alpha-Phellandrene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-0fe1966be3faee829dec2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-alpha-Phellandrene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 10V, Positive-QTOFsplash10-000i-2900000000-84435206059b57657bff2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 20V, Positive-QTOFsplash10-000i-9600000000-f16481e876627d7d4bdf2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 40V, Positive-QTOFsplash10-1000-9100000000-6993cdda47b7e020b82d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 10V, Negative-QTOFsplash10-000i-0900000000-380abae33f914a4d40012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 20V, Negative-QTOFsplash10-000i-0900000000-099421ca3a157c7e1c712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 40V, Negative-QTOFsplash10-00ku-7900000000-58a61cb646aec74939282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 10V, Positive-QTOFsplash10-000m-9500000000-57eb4e7b936ea365be202021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 20V, Positive-QTOFsplash10-002f-9000000000-7265bcee351c38f0f79c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 40V, Positive-QTOFsplash10-00ou-9000000000-0d460f957e928551b42c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 10V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 20V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-alpha-Phellandrene 40V, Negative-QTOFsplash10-0uxr-9000000000-5a30982006f09d04cfc82021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013568
KNApSAcK IDNot Available
Chemspider ID391432
KEGG Compound IDC11391
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443160
PDB IDNot Available
ChEBI ID367
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1374391
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.