Limonene (CED0001962)

Record Information
Version1.0
Creation Date2016-05-22 04:13:23 UTC
Update Date2026-05-14 20:12:29 UTC
Accession NumberCHEM017298
Identification
Common NameLimonene
ClassSmall Molecule
Description
Limonene (C10H16) is a compound with an average molecular weight of 136.24 g/mol. Limonene belongs to the monoterpenoids, a subclass of prenol lipids within the organic compounds. This substance serves several industrial roles and uses, including acting as a fragrance, a deodorizer, and a flavouring and nutrient. It is utilized industrially as a solvent (PMC10370462), a food additive (PMC9316819), and as both an insecticide and a pesticide (PMC10775899). Biologically, it functions as an antioxidant (PMC8306454) and an inhibitor (PMC13025514). Regarding health effects, limonene is a treatment for gastroesophageal reflux disease (PMC3396330) and has a therapeutic effect on inflammation (PMC9583546). Limonene is found in or released from 34 recorded sources. These include household cleaning and consumer products such as bleaching agents, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and pipe accessories. It is also associated with electrical and electronic equipment, including antennas, communication cables or conductors, contacts, discharge lamps, and electric switches. Further sources include coins, indoor air, and building and construction materials such as tents or canopies and sunshades awnings or outside screens. In food, food processing and cookware, it is found in food contact materials, the processing of meats, and fermentation processes for beer, wort, and the preparation of wine or sparkling wine. Recorded exposure routes include touch, oral, and inhalation, with literature support specifically for inhalation (PMC12477777).
Contaminant Type
  • Insecticide
Chemical Structure
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 Mass136.238 g/mol
Monoisotopic Mass136.125 g/mol
CAS Registry Number138-86-3
IUPAC Name1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
Traditional Namelimonene, (+)-
SMILESCC(=C)C1CCC(C)=CC1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0006-9300000000-132287e3db63dda49102Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00kf-9300000000-d7348db845e3e79845ddNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9200000000-df40612bbf371089d7acNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4o-9000000000-893d8151186383a89b6aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-2900000000-bce8f8616cfd3b16cac9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9600000000-583a2621a826cedbca61Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-1000-9100000000-d78cd6fbdd7a13fe9dfaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-2950ad058f77d7bc9f76Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-6f48f3b0b500d4f25ec9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-5900000000-1c30c00bfa4058f5e22bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001a-9400000000-fb09a1cdd4bc09480281Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0564-9000000000-dc5effa7f00987fc8567Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00mo-9000000000-40d99aa482e2ce5a66f1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-a013b4ae27f975ab5621Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-a013b4ae27f975ab5621Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-8900000000-d835e92fba2c2a238797Not AvailableView Spectrum
MSMS Spectrumsplash10-014l-9100000000-498293086493b60c2094Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2991.0Log mg/kg[1700:5300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationhas_therapeutic_effect_onNot AvailablePMC9583546
gastroesophageal reflux diseaseis_treatment_forNot AvailablePMC3396330
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
233BrushesPersonal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
571CoinsHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)72.789
Click to view 3D structurePyruvate kinase PKMP52480Mus musculusPredicted (SEA)1.24559
Gamma-aminobutyric acid receptor subunit beta-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit beta-2P47870HumansPredicted (SEA)2.33548
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)585.66
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)127.439
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)260.795
Click to view 3D structureHeat sensitive channel TRPV3Q4QYD9Rattus norvegicusPredicted (SEA)1.86838
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)1999.95
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)1631.49
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q6RI86Rattus norvegicusPredicted (SEA)95.9881
Transient receptor potential cation channel subfamily M member 8 structureClick to view 3D structureTransient receptor potential cation channel subfamily M member 8Q7Z2W7HumansPredicted (SEA)98.7128
G-protein coupled receptor 55 structureClick to view 3D structureG-protein coupled receptor 55Q9Y2T6HumansPredicted (SEA)550.394
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)4879.43
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)399.834
Click to view 3D structureTransient receptor potential cation channel subfamily M member 8Q8R455Rattus norvegicusPredicted (SEA)87.1911
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)5647.03
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)2683.31
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansPredicted (SEA)1752.85
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)5160.86
Taste receptor type 2 member 46 structureClick to view 3D structureTaste receptor type 2 member 46P59540HumansPredicted (SEA)0.311397
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)4391.01
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)5373.08
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)5893.03
Click to view 3D structureCannabinoid receptor 1P47746Mus musculusPredicted (SEA)560.437
Click to view 3D structureCannabinoid receptor 2P47936Mus musculusPredicted (SEA)791.649
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0032473
FooDB IDFDB014115
Phenol Explorer IDNot Available
KNApSAcK IDC00003043
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID20939
ChEBI ID15384
PubChem Compound ID22311
Kegg Compound IDC06078
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM