Record Information
Version1.0
Creation date2010-04-08 22:11:11 UTC
Update date2019-11-26 03:09:48 UTC
Primary IDFDB014297
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-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.
CAS Number5989-27-5
Structure
Thumb
Synonyms
SynonymSource
(+)-(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
(4S)-1-Methyl-4-isopropenylcyclohex-1-eneHMDB
1-Methyl-4-(1-methylethenyl)cyclohexeneHMDB
LimoneneHMDB
Limonene, (+-)-isomerHMDB
(D)-LimoneneHMDB
4-Mentha-1,8-dieneHMDB
Limonene, (S)-isomerHMDB
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
D-LimoneneChEBI
d-LimoneneHMDB
(+)-(R)-4-Isopropenyl-1-methylcyclohexeneMeSH
D LimoneneMeSH
4 Mentha 1,8 dieneMeSH
(R)-4-Isopropenyl-1-methylcyclohexeneMeSH
(+)-(r)-limonenebiospider
(+)-1,8-para-Menthadienebiospider
(+)-carvenebiospider
(+)-limonenebiospider
(+)-r-limonenebiospider
(4R)-1-methyl-4-(1-methylethenyl)cyclohexenebiospider
(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-enebiospider
(4R)-1-methyl-4-isopropenylcyclohex-1-enebiospider
(4R)-4-isopropenyl-1-methylcyclohexenebiospider
(d)-limonenebiospider
(r)-(+)-limonenebiospider
(R)-1-methyl-4-(1-methylethenyl)cyclohexenebiospider
(r)-limonenebiospider
1-Methyl-4-(1-methylethenyl)cyclohexene, (R)-biospider
4betaH-p-mentha-1,8-dienemanual
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-biospider
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-biospider
D-(+)-limonenebiospider
D-1,8-p-Menthadienebiospider
D-limonenbiospider
D-limonenebiospider
d-p-Mentha-1,8-dienebiospider
Dextro-limonenebiospider
p-Mentha-1,8-diene, (R)-(+)-biospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16
IUPAC name(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
InChI IdentifierInChI=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
Isomeric SMILESCC(=C)[C@@H]1CCC(C)=CC1
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting Point-74.3 oC
Boiling PointBp20 71°DFC
Experimental Water Solubility0.0138 mg/mL at 25 oCMASSALDI,HA & KING,CJ (1973)
Experimental logP4.57LI,J & PURDUE,EM (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +126.8DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0173-9100000000-239928f205c8242a700aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-507f7afbc17b7c2556e2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-1a0c62c6971532ab6782JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0173-9100000000-239928f205c8242a700aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-507f7afbc17b7c2556e2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-1a0c62c6971532ab6782JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-df40612bbf371089d7acJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-6900000000-f7ee4bad43b6ccae0ccbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ou-9000000000-51a52c25a98124e179e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-9655665d3d36755028ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0173-9100000000-239928f205c8242a700aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-014l-9100000000-bc8708fdb2d1955dce92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-014l-9100000000-1a0c62c6971532ab6782JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-bce8f8616cfd3b16cac9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9600000000-583a2621a826cedbca61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-d78cd6fbdd7a13fe9dfaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-2950ad058f77d7bc9f76JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-6f48f3b0b500d4f25ec9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-5900000000-1c30c00bfa4058f5e22bJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-fbf154446f93ee5019c0JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID389747
ChEMBL IDCHEMBL449062
KEGG Compound IDC06099
Pubchem Compound ID440917
Pubchem Substance IDNot Available
ChEBI ID15382
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04321
CRC / DFC (Dictionary of Food Compounds) IDJFH51-A:JPJ51-C
EAFUS ID2034
Dr. Duke IDD-(+)-LIMONENE|D-LIMONENE|(+)-LIMONENE
BIGG IDNot Available
KNApSAcK IDC00010868
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID5989-27-5
GoodScent IDrw1013771
SuperScent ID440917
Wikipedia IDLimonene
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti acetylcholinesterase38462 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
apoptoticDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
differentiatorDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
hypocholesterolemicDUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
litholyticDUKE
nephrotoxic50909 A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals.DUKE
cytochrome-P450-2B1 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
citrus
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mint
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
lemon
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
orange
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.