Record Information
Version1.0
Creation Date2016-05-19 02:12:08 UTC
Update Date2016-11-09 01:09:42 UTC
Accession NumberCHEM006292
Identification
Common NameLEMON, OIL (CITRUS LIMON (L.) BURM. F.)
ClassSmall Molecule
DescriptionA monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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 Number8008-56-8
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9300000000-132287e3db63dda49102Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9300000000-d7348db845e3e79845ddSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-df40612bbf371089d7acSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4o-9000000000-893d8151186383a89b6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-bce8f8616cfd3b16cac9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9600000000-583a2621a826cedbca61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-d78cd6fbdd7a13fe9dfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-2950ad058f77d7bc9f76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-6f48f3b0b500d4f25ec9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-5900000000-1c30c00bfa4058f5e22bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001a-9400000000-fb09a1cdd4bc09480281Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0564-9000000000-dc5effa7f00987fc8567Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-40d99aa482e2ce5a66f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab5621Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab5621Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-8900000000-d835e92fba2c2a238797Spectrum
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-498293086493b60c2094Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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