Showing Compound Card for (-)-Limonene (CDB005271)

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Record Information
Version1.0
Created at2020-04-17 19:26:28 UTC
Updated at2020-12-07 19:11:52 UTC
CannabisDB IDCDB005271
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(-)-Limonene
Descriptiond-Limonene, also known as dipentene, 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. Thus, D-limonene is considered to be an isoprenoid lipid molecule. d-Limonene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (-)-Limonene is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-(4R)-LimoneneChEBI
(+)-(R)-LimoneneChEBI
(+)-4-Isopropenyl-1-methylcyclohexeneChEBI
(+)-LimoneneChEBI
(4R)-1-Methyl-4-isopropenylcyclohex-1-eneChEBI
(4R)-4-Isopropenyl-1-methylcyclohexeneChEBI
(R)-(+)-LimoneneChEBI
(R)-(+)-p-Mentha-1,8-dieneChEBI
(R)-1-Methyl-4-(1-methylethenyl)cyclohexeneChEBI
(R)-4-Isopropenyl-1-methyl-1-cyclohexeneChEBI
(R)-p-Mentha-1,8-dieneChEBI
4BetaH-p-mentha-1,8-dieneChEBI
D-(+)-LimoneneChEBI
D-LimonenChEBI
AISA 5203-L (+)limoneneHMDB
DipenteneHMDB
(-)-LimoneneHMDB
1-Methyl-4-(1-methylethenyl)cyclohexeneHMDB
LimoneneHMDB
Limonene, (+-)-isomerHMDB
(D)-LimoneneHMDB
4-Mentha-1,8-dieneHMDB
Limonene, (R)-isomerHMDB
(+)-DipenteneHMDB
(+)-alpha-LimoneneHMDB
(+)-p-Mentha-1,8-dieneHMDB
(+)-Α-limoneneHMDB
(4R)-(+)-LimoneneHMDB
(4R)-1-Methyl-4-(1-methylethenyl)cyclohexeneHMDB
(4R)-LimoneneHMDB
(R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-eneHMDB
(R)-LimoneneHMDB
1-Methyl-4-prop-1-en-2-yl-cyclohexeneHMDB
(+)-(R)-4-Isopropenyl-1-methylcyclohexeneHMDB
D LimoneneHMDB
4 Mentha 1,8 dieneHMDB
(R)-4-Isopropenyl-1-methylcyclohexeneHMDB
D-LimoneneChEBI
d-LimoneneHMDB
(4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-eneHMDB
R-LimoneneHMDB
p-Mentha-1,8-dienePhytoBank
(±)-DipentenePhytoBank
(±)-LimonenePhytoBank
(±)-alpha-LimonenePhytoBank
(±)-α-LimonenePhytoBank
1,8-p-MenthadienePhytoBank
1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-enePhytoBank
1-Methyl-4-isopropenyl-1-cyclohexenePhytoBank
1-Methyl-4-isopropenylcyclohexenePhytoBank
1-Methyl-p-isopropenyl-1-cyclohexenePhytoBank
4-Isopropenyl-1-methyl-1-cyclohexenePhytoBank
4-Isopropenyl-1-methylcyclohexenePhytoBank
dl-LimonenePhytoBank
DipentenPhytoBank
LimonenPhytoBank
alpha-LimonenePhytoBank
α-LimonenePhytoBank
Chemical FormulaC10H16
Average Molecular Weight136.23
Monoisotopic Molecular Weight136.1252
IUPAC Name(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
Traditional Nameα-limonene
CAS Registry Number5989-27-5
SMILES
CC(=C)[C@@H]1CCC(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/t10-/m0/s1
InChI KeyXMGQYMWWDOXHJM-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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-90 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP4.38GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-fbf154446f93ee5019c02015-03-01View Spectrum
GC-MS(-)-Limonene, non-derivatized, GC-MS Spectrumsplash10-0173-9100000000-239928f205c8242a700aSpectrum
GC-MS(-)-Limonene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-507f7afbc17b7c2556e2Spectrum
GC-MS(-)-Limonene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-1a0c62c6971532ab6782Spectrum
GC-MS(-)-Limonene, non-derivatized, GC-MS Spectrumsplash10-0173-9100000000-239928f205c8242a700aSpectrum
GC-MS(-)-Limonene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-507f7afbc17b7c2556e2Spectrum
GC-MS(-)-Limonene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-1a0c62c6971532ab6782Spectrum
GC-MS(-)-Limonene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-0b286d388287bcc487f2Spectrum
Predicted GC-MS(-)-Limonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9200000000-df40612bbf371089d7acSpectrum
Predicted GC-MS(-)-Limonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-6900000000-f7ee4bad43b6ccae0ccb2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ou-9000000000-51a52c25a98124e179e92012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-9655665d3d36755028cc2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0173-9100000000-239928f205c8242a700a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-014l-9100000000-bc8708fdb2d1955dce922012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-014l-9100000000-1a0c62c6971532ab67822012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-bce8f8616cfd3b16cac92017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9600000000-583a2621a826cedbca612017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-d78cd6fbdd7a13fe9dfa2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-2950ad058f77d7bc9f762017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-6f48f3b0b500d4f25ec92017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-5900000000-1c30c00bfa4058f5e22b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-8900000000-d835e92fba2c2a2387972021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001a-9400000000-fb09a1cdd4bc094802812021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0564-9000000000-dc5effa7f00987fc85672021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-40d99aa482e2ce5a66f12021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytochrome P450 2C9CYP2C910q24P11712 details
Cytochrome P450 2C19CYP2C1910q24P33261 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003375
DrugBank IDDB08921
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006329
KNApSAcK IDC00010868
Chemspider ID389747
KEGG Compound IDC06099
BioCyc IDCPD-4886
BiGG IDNot Available
Wikipedia LinkLimonene
METLIN IDNot Available
PubChem Compound440917
PDB IDNot Available
ChEBI ID15382
References
General ReferencesNot Available