Record Information
Version1.0
Creation date2010-04-08 22:10:47 UTC
Update date2015-07-20 23:00:21 UTC
Primary IDFDB013567
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLimonene
DescriptionFound in over 300 essential oils, the ==(R)==-form is the most widespread, followed by the racemate and then the (S)-form. Extensively used in the flavour industry [DFC]
CAS Number138-86-3
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
D LimoneneMeSH
(R)-4-Isopropenyl-1-methylcyclohexeneMeSH
4 Mentha 1,8 dieneMeSH
1-Methyl-4-(1-methylethenyl)cyclohexene, 9CIdb_source
1,8-p-menthadienemanual
4-isopropenyl-1-methylcyclohexenedb_source
Carvenedb_source
Citrenedb_source
Cynenedb_source
Diisoprenedb_source
FEMA 2633db_source
Hesperidenedb_source
Isoterebentinedb_source
Kautschinedb_source
p-Mentha-1,8-dienedb_source
Terpilenedb_source
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
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateliquid
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting Point-95 oC
Boiling PointNot Available
Experimental Water Solubility0.00757 mg/mL at 25 oCMILLER,DJ & HAWTHORNE,SB (2000A)
Experimental logP4.57LI,J & PERDUE,EM (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9300000000-132287e3db63dda49102View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9300000000-d7348db845e3e79845ddView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-df40612bbf371089d7acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-bce8f8616cfd3b16cac9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9600000000-583a2621a826cedbca61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-d78cd6fbdd7a13fe9dfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-2950ad058f77d7bc9f76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-6f48f3b0b500d4f25ec9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-5900000000-1c30c00bfa4058f5e22bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-498293086493b60c2094View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC06078
Pubchem Compound ID22311
Pubchem Substance IDNot Available
ChEBI ID15384
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJFH51-A:JFH51-A
EAFUS IDNot Available
Dr. Duke IDLIMONENE|CARVENE
BIGG ID47361
KNApSAcK IDC00000823
HET IDNot Available
Flavornet ID138-86-3
GoodScent IDNot Available
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
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
acetylcholinesterase inhibitor38462 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
allelochemicDUKE
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 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 adenomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti esophagiticDUKE
anti feedantDUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti lithicDUKE
anti lymphomicDUKE
anti metastatic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mutagenicDUKE
anti obesity52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
bronchoprotectant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidistatDUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cholesterolyticDUKE
cytochrome-p450 inducerDUKE
detoxicant50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
enterocontractantDUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungiphilicDUKE
fungistatDUKE
glutathione-S-transferase inducerDUKE
herbicide24527 A substance used to destroy plant pests.DUKE
histaminicDUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
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
interleukin-6 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
irritantDUKE
lipolyticDUKE
myorelaxantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
nitric-oxide-genicDUKE
ornithine-decarboxylase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
ozone scavengerDUKE
peristalticDUKE
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
photosensitizerDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
transdermalDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
lemon
  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
orange
  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
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.