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Showing Compound (S)-Limonene (FDB013861)

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
MOLSDFPDBSMILESInChI
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
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-fbf154446f93ee5019c02015-03-01View Spectrum
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-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
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.