Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:59 UTC
Update Date2022-03-07 02:53:22 UTC
HMDB IDHMDB0032473
Secondary Accession Numbers
  • HMDB32473
Metabolite Identification
Common NamePolylimonene
DescriptionPolylimonene, also known as (+/-)-limonene or cajeputene, 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. Based on a literature review a significant number of articles have been published on Polylimonene.
Structure
Data?1563862268
Synonyms
ValueSource
(+-)-(RS)-LimoneneChEBI
(+/-)-limoneneChEBI
1,8-p-MenthadieneChEBI
1-Methyl-4-(1-methylethenyl)cyclohexeneChEBI
4-Isopropenyl-1-methylcyclohexeneChEBI
CajeputeneChEBI
DipenteneChEBI
DL-LimoneneChEBI
KautschinChEBI
LimoneneKegg
(+/-)-P-mentha-1,8-diene homopolymerHMDB
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, homopolymerHMDB
Dipentene polymerHMDB
Dipentene, homopolymerHMDB
Limonene polymerHMDB
P-Mentha-1,8-diene, homopolymer (7ci)HMDB
P-Mentha-1,8-diene, polymers (8ci)HMDB
PolydipenteneHMDB
(D)-LimoneneMeSH, HMDB
AISA 5203-L (+)limoneneMeSH, HMDB
(4S)-1-Methyl-4-isopropenylcyclohex-1-eneMeSH, HMDB
D-LimoneneMeSH, HMDB
Limonene, (R)-isomerMeSH, HMDB
(-)-LimoneneMeSH, HMDB
4-Mentha-1,8-dieneMeSH, HMDB
(+)-LimoneneMeSH, HMDB
Limonene, (+-)-isomerMeSH, HMDB
Limonene, (S)-isomerMeSH, HMDB
(+)-(R)-4-Isopropenyl-1-methylcyclohexeneMeSH
(4R)-1-Methyl-4-(1-methylethenyl)cyclohexeneMeSH
(R)-(+)-LimoneneMeSH
(R)-4-Isopropenyl-1-methylcyclohexeneMeSH
D LimoneneMeSH
4 Mentha 1,8 dieneMeSH
Chemical FormulaC10H16
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
IUPAC Name1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
Traditional Namelimonene, (+)-
CAS Registry Number9003-73-0
SMILES
CC(=C)C1CCC(C)=CC1
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3
InChI KeyXMGQYMWWDOXHJM-UHFFFAOYSA-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
Physiological effect
Disposition
Source
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP4.5ALOGPS
logP3.22ChemAxon
logS-2.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.48 m³·mol⁻¹ChemAxon
Polarizability17.55 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]+132.18431661259
DarkChem[M-H]-127.59631661259
DeepCCS[M+H]+134.02830932474
DeepCCS[M-H]-131.17330932474
DeepCCS[M-2H]-167.88130932474
DeepCCS[M+Na]+143.27530932474
AllCCS[M+H]+127.732859911
AllCCS[M+H-H2O]+123.032859911
AllCCS[M+NH4]+132.032859911
AllCCS[M+Na]+133.332859911
AllCCS[M-H]-132.732859911
AllCCS[M+Na-2H]-134.532859911
AllCCS[M+HCOO]-136.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PolylimoneneCC(=C)C1CCC(C)=CC11202.1Standard polar33892256
PolylimoneneCC(=C)C1CCC(C)=CC11017.7Standard non polar33892256
PolylimoneneCC(=C)C1CCC(C)=CC11016.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Polylimonene GC-MS (Non-derivatized)splash10-0006-9300000000-132287e3db63dda491022014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Polylimonene EI-B (Non-derivatized)splash10-00kf-9300000000-d7348db845e3e79845dd2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Polylimonene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-df40612bbf371089d7ac2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Polylimonene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-498293086493b60c20942015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Polylimonene 35V, Positive-QTOFsplash10-0a4o-9000000000-893d8151186383a89b6a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 10V, Positive-QTOFsplash10-000i-2900000000-bce8f8616cfd3b16cac92016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 20V, Positive-QTOFsplash10-000i-9600000000-583a2621a826cedbca612016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 40V, Positive-QTOFsplash10-1000-9100000000-d78cd6fbdd7a13fe9dfa2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 10V, Negative-QTOFsplash10-000i-0900000000-2950ad058f77d7bc9f762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 20V, Negative-QTOFsplash10-000i-0900000000-6f48f3b0b500d4f25ec92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 40V, Negative-QTOFsplash10-014r-5900000000-1c30c00bfa4058f5e22b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 10V, Positive-QTOFsplash10-001a-9400000000-fb09a1cdd4bc094802812021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 20V, Positive-QTOFsplash10-0564-9000000000-dc5effa7f00987fc85672021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 40V, Positive-QTOFsplash10-00mo-9000000000-40d99aa482e2ce5a66f12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 10V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 20V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Polylimonene 40V, Negative-QTOFsplash10-014i-8900000000-d835e92fba2c2a2387972021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014115
KNApSAcK IDC00003043
Chemspider ID20939
KEGG Compound IDC06078
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22311
PDB IDNot Available
ChEBI ID15384
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.