Showing Compound Card for Limonene (CDB000069)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:23:38 UTC
Updated at2020-12-07 19:07:02 UTC
CannabisDB IDCDB000069
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameLimonene
DescriptionLimonene or dipentene, belongs to the class of organic compounds known as menthane monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. Para-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. Limonene exists as a clear colourless liquid at room temperature. Industrially limonene is used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. Limonene is often marketed as a botanical (plant-derived) solvent of low toxicity. It is a chiral molecule, and biological sources produce only one enantiomer, the D-isomer. Limonene is one of the monoterpenes identified in Cannabis sativa (PMID: 6991645 ). It is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). D-Limonene is a major component of the aromatic scents and resins characteristic of numerous coniferous and broadleaved trees including red and silver maple, cottonwoods, aspens, spruce, various pines, Douglas fir, larches and cedars. D-Limonene is the major component in oil of oranges. Because of its pleasant odor, limonene is widely used as a flavour and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). As the main fragrance of citrus peels, D-limonene is used in food manufacturing and some medicines, such as a flavoring to mask the bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions, bath products, and other personal care products. Limonene is also used as a botanical insecticide. Mild skin irritation may occur from exposure to limonene and oxidation products of limonene may produce dermal sensitization and may have irritative and bronchoconstrictive airway effects. Limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Limonene is one of the active components of dietary phytochemicals that appears to be protective against cancer (PMID: 16563357 , 15499193 , 15325315 , 2024047 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(S)-LimoneneChEBI
(-)-(4S)-LimoneneChEBI
(4S)-1-Methyl-4-isopropenylcyclohex-1-eneChEBI
(4S)-4-Isopropenyl-1-methylcyclohexeneChEBI
(S)-(-)-p-Mentha-1,8-dieneChEBI
(S)-1-Methyl-4-(1-methylethenyl)cyclohexeneChEBI
(S)-p-Mentha-1,8-dieneChEBI
4AlphaH-p-mentha-1,8-dieneChEBI
L-LimonenChEBI
L-LimoneneChEBI
4-Isopropenyl-1-methyl-1-cyclohexeneHMDB
LimoneneHMDB
(+)-LimoneneHMDB
AISA 5203-L (+)limoneneHMDB
DipenteneHMDB
1-Methyl-4-(1-methylethenyl)cyclohexeneHMDB
Limonene, (+-)-isomerHMDB
(D)-LimoneneHMDB
4-Mentha-1,8-dieneHMDB
Limonene, (S)-isomerHMDB
Limonene, (R)-isomerHMDB
(R)-(+)-LimoneneHMDB
(R)-4-Isopropenyl-1-methylcyclohexeneHMDB
(+)-(R)-4-Isopropenyl-1-methylcyclohexeneHMDB
(4R)-1-Methyl-4-(1-methylethenyl)cyclohexeneHMDB
D-LimoneneHMDB
4 Mentha 1,8 dieneHMDB
D LimoneneHMDB
(-)-alpha-LimoneneHMDB
(-)-Α-limoneneHMDB
(4S)-1-Methyl-4-(1-methylethenyl)cyclohexeneHMDB
(4S)-LimoneneHMDB
(S)-(-)-LimoneneHMDB
(S)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-eneHMDB
(S)-4-Isopropenyl-1-methyl-1-cyclohexeneHMDB
(S)-LimoneneHMDB
beta-LimoneneHMDB
L-CarveneHMDB
Β-limoneneHMDB
(-)-LimoneneChEBI
Chemical FormulaC10H16
Average Molecular Weight136.23
Monoisotopic Molecular Weight136.1252
IUPAC Name(4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
Traditional Name(-)-limonene
CAS Registry Number5989-54-8
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-/m1/s1
InChI KeyXMGQYMWWDOXHJM-SNVBAGLBSA-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

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-74.3 °CNot Available
Boiling Point176 °CWikipedia
Water Solubility0.014 mg/mL at 25 °CNot Available
logP4.57LI,J & PURDUE,EM (1995)
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
Polarizability17.23 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-9100000000-7e8881e736cecb723a2b2015-03-01View Spectrum
GC-MSLimonene, non-derivatized, GC-MS Spectrumsplash10-0173-9100000000-239928f205c8242a700aSpectrum
GC-MSLimonene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-507f7afbc17b7c2556e2Spectrum
GC-MSLimonene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-1a0c62c6971532ab6782Spectrum
GC-MSLimonene, non-derivatized, GC-MS Spectrumsplash10-0173-9100000000-239928f205c8242a700aSpectrum
GC-MSLimonene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-507f7afbc17b7c2556e2Spectrum
GC-MSLimonene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-1a0c62c6971532ab6782Spectrum
Predicted GC-MSLimonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fgo-9200000000-a79c6ccef83c7113ab9fSpectrum
Predicted GC-MSLimonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001c-8900000000-dfd6c14e6a4e49bfc6dc2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002f-9000000000-06c43b864c090aaae8ae2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01t9-9000000000-e5ee54500bc5feda46312012-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900000000-5567709cc9ec1c9909db2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9600000000-4570df18c5140586d0bf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-61312f12f069cd9de75c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-88ada45edfe65d9e7f3a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-1192305465e6c746cfa92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-4900000000-199ee0c6ed49a35bcff42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001a-9400000000-fb09a1cdd4bc094802812021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0564-9000000000-dc5effa7f00987fc85672021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-40d99aa482e2ce5a66f12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-8900000000-d835e92fba2c2a2387972021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 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
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.86 mg/g dry wt
    • David S. Wishart,...
 details
Alien Dawg (Indica dominant)Detected and Quantified1.44 +/- 0.27 mg/g dry wt
    • David S. Wishart,...
 details
Animal CookiesDetected and Quantified3.8 +/- 0.9 mg/g dry wt details
Blue CookiesDetected and Quantified2.5 +/- 0.9 mg/g dry wt details
Blue DreamDetected and Quantified1.1 +/- 0.8 mg/g dry wt details
Bubba KushDetected and Quantified3 +/- 1.1 mg/g dry wt details
ChemdogDetected and Quantified4.2 +/- 1.1 mg/g dry wt details
Crown OgDetected and Quantified5.1 +/- 1.6 mg/g dry wt details
Fortune CookiesDetected and Quantified3.6 +/- 1 mg/g dry wt details
GabriolaDetected and Quantified2.48 mg/g dry wt
    • David S. Wishart,...
 details
GasDetected and Quantified5.9 +/- 1.7 mg/g dry wt details
GelatoDetected and Quantified9.1 +/- 1.6 mg/g dry wt details
Girl Scout CookiesDetected and Quantified3.4 +/- 1 mg/g dry wt details
GodfatherDetected and Quantified1.9 +/- 0.6 mg/g dry wt details
Gorilla Glue #4Detected and Quantified4.2 +/- 1.1 mg/g dry wt details
Island HoneyDetected and Quantified0.12 mg/g dry wt
    • David S. Wishart,...
 details
Jack HererDetected and Quantified0.9 +/- 0.4 mg/g dry wt details
Master KushDetected and Quantified3.2 +/- 1.3 mg/g dry wt details
Miami White KushDetected and Quantified8.3 +/- 1.3 mg/g dry wt details
Mr. NiceDetected and Quantified3.4 +/- 1.2 mg/g dry wt details
Og KushDetected and Quantified5.4 +/- 2.5 mg/g dry wt details
QuadraDetected and Quantified1.38 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.18 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.27 +/- 0.02 mg/g dry wt
    • David S. Wishart,...
 details
SherbertDetected and Quantified5.2 +/- 0.9 mg/g dry wt details
Skywalker Og KushDetected and Quantified5.1 +/- 1.5 mg/g dry wt details
Sour DieselDetected and Quantified4.4 +/- 1.1 mg/g dry wt details
Strawberry HazeDetected and Quantified2.4 +/- 0.5 mg/g dry wt details
Superman Og KushDetected and Quantified6.3 +/- 1.7 mg/g dry wt details
Tahoe Og KushDetected and Quantified6.8 +/- 1.3 mg/g dry wt details
Tangerine DreamDetected and Quantified0.26 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine Dream (Sativa dominant)Detected and Quantified0.19 +/- 0.02 mg/g dry wt
    • David S. Wishart,...
 details
Thin MintsDetected and Quantified3.3 +/- 0.9 mg/g dry wt details
TrainwreckDetected and Quantified3.4 +/- 1.9 mg/g dry wt details
Triple ODetected and Quantified6.7 +/- 1.4 mg/g dry wt details
HMDB IDHMDB0004321
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006329
KNApSAcK IDC00000803
Chemspider ID388386
KEGG Compound IDC00521
BioCyc IDNot Available
BiGG ID47361
Wikipedia LinkLimonene
METLIN ID6911
PubChem Compound439250
PDB IDNot Available
ChEBI ID15383
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. Flamm WG, Lehman-McKeeman LD: The human relevance of the renal tumor-inducing potential of d-limonene in male rats: implications for risk assessment. Regul Toxicol Pharmacol. 1991 Feb;13(1):70-86. doi: 10.1016/0273-2300(91)90042-t. [PubMed:2024047 ]
  3. Aggarwal BB, Shishodia S: Molecular targets of dietary agents for prevention and therapy of cancer. Biochem Pharmacol. 2006 May 14;71(10):1397-421. doi: 10.1016/j.bcp.2006.02.009. Epub 2006 Feb 23. [PubMed:16563357 ]
  4. Tsuda H, Ohshima Y, Nomoto H, Fujita K, Matsuda E, Iigo M, Takasuka N, Moore MA: Cancer prevention by natural compounds. Drug Metab Pharmacokinet. 2004 Aug;19(4):245-63. doi: 10.2133/dmpk.19.245. [PubMed:15499193 ]
  5. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  6. DeWitt C, Bebarta V: Botanical solvents. Clin Occup Environ Med. 2004 Aug;4(3):445-54, v-vi. doi: 10.1016/j.coem.2004.03.003. [PubMed:15325315 ]