Record Information
Version1.0
Creation date2010-04-08 22:11:05 UTC
Update date2018-05-29 01:09:45 UTC
Primary IDFDB014115
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(±)-Limonene
DescriptionConstituent of many essential oils. (±)-Limonene is found in many foods, some of which are common oregano, nutmeg, herbs and spices, and summer savory.
CAS Number9003-73-0
Structure
Thumb
Synonyms
SynonymSource
(+-)-(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)-LimoneneHMDB
AISA 5203-L (+)limoneneHMDB
(4S)-1-Methyl-4-isopropenylcyclohex-1-eneHMDB
D-LimoneneHMDB
Limonene, (R)-isomerHMDB
(-)-LimoneneHMDB
4-Mentha-1,8-dieneHMDB
(+)-LimoneneHMDB
Limonene, (+-)-isomerHMDB
Limonene, (S)-isomerHMDB
(+)-(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
(+-)-Dipentenemanual
(+-)-Limonenemanual
(+/-)-P-mentha-1,8-diene homopolymerHMDB
(±)-Dipentenemanual
(±)-Limonenemanual
(R/S)-Limonenemanual
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 name1-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
InChI KeyXMGQYMWWDOXHJM-UHFFFAOYSA-N
Isomeric SMILESCC(=C)C1CCC(C)=CC1
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting Point< 25 oC
Boiling PointBp 178°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID20939
ChEMBL IDNot Available
KEGG Compound IDC06078
Pubchem Compound ID22311
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32473
CRC / DFC (Dictionary of Food Compounds) IDJFH51-A:JNZ87-F
EAFUS ID2036
Dr. Duke IDDL-LIMONENE|DIPENTENE
BIGG IDNot Available
KNApSAcK IDC00003043
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1240221
SuperScent IDNot Available
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
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
irritantDUKE
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
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
citrus
  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.
terpene
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
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.