Record Information
Version1.0
Creation date2010-04-08 22:10:57 UTC
Update date2019-11-26 03:09:11 UTC
Primary IDFDB013861
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-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 Number5989-54-8
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
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
(-)-(4S)-Limonenebiospider
(-)-(s)-limonenebiospider
(-)-carvenebiospider
(-)-p-Mentha-1,8-dienebiospider
(4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-enebiospider
(4S)-1-methyl-4-isopropenylcyclohex-1-enebiospider
(4S)-4-isopropenyl-1-methylcyclohexenebiospider
(4S)-limonenebiospider
(s)-(-)-limonenebiospider
(S)-(-)-p-mentha-1,8-dienebiospider
(S)-1-methyl-4-(1-methylethenyl)cyclohexenebiospider
(S)-4-Isopropenyl-1-methyl cyclohexenebiospider
(S)-p-mentha-1,8-dienebiospider
4alphaH-p-mentha-1,8-dienebiospider
L-limonenbiospider
L-limonenebiospider
p-Mentha-1,8-diene, (S)-(-)-biospider
S-(-)-limonenebiospider
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
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-90 oC
Boiling PointBp 177.6-177.8°DFC
Experimental Water SolubilityNot Available
Experimental logP4.38GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -122.6DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-fbf154446f93ee5019c0Spectrum
GC-MS(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrumsplash10-0173-9100000000-239928f205c8242a700aSpectrum
GC-MS(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-507f7afbc17b7c2556e2Spectrum
GC-MS(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-1a0c62c6971532ab6782Spectrum
GC-MS(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrumsplash10-0173-9100000000-239928f205c8242a700aSpectrum
GC-MS(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-507f7afbc17b7c2556e2Spectrum
GC-MS(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-1a0c62c6971532ab6782Spectrum
GC-MS(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-0b286d388287bcc487f2Spectrum
Predicted GC-MS(+)-Mentha-1,8-diene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9200000000-df40612bbf371089d7acSpectrum
Predicted GC-MS(+)-Mentha-1,8-diene, 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-f7ee4bad43b6ccae0ccbSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ou-9000000000-51a52c25a98124e179e9Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-9655665d3d36755028ccSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0173-9100000000-239928f205c8242a700aSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-014l-9100000000-bc8708fdb2d1955dce92Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-014l-9100000000-1a0c62c6971532ab6782Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-bce8f8616cfd3b16cac9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9600000000-583a2621a826cedbca61Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-d78cd6fbdd7a13fe9dfaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-2950ad058f77d7bc9f76Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-6f48f3b0b500d4f25ec9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-5900000000-1c30c00bfa4058f5e22bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab5621Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab5621Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-8900000000-d835e92fba2c2a238797Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001a-9400000000-fb09a1cdd4bc09480281Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0564-9000000000-dc5effa7f00987fc8567Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-40d99aa482e2ce5a66f1Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID388386
ChEMBL IDCHEMBL236688
KEGG Compound IDC00521
Pubchem Compound ID439250
Pubchem Substance IDNot Available
ChEBI ID15383
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03375
CRC / DFC (Dictionary of Food Compounds) IDJFH51-A:JJF05-H
EAFUS ID2035
Dr. Duke IDL-LIMONENE|DELTA-LIMONENE|(-)-LIMONENE
BIGG ID47361
KNApSAcK IDC00000803
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1007831
SuperScent ID439250
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
camphoraceous
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
terpene
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pine
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
peppery
  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.