Record Information
Version1.0
Creation date2010-04-08 22:11:11 UTC
Update date2019-11-26 03:09:48 UTC
Primary IDFDB014297
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-Limonene
DescriptionMajor constituent of oil of orange rind, dill oil, oil of cumin, bergamot, caraway, lemon balm and lemon. obtained comly. from orange oil on a large scale (ca. 50000 T/a). Flavouring agent. Nutriceutical with anticancer props. (R)-Limonene is found in many foods, some of which are citrus, nutmeg, guava, and cardamom.
CAS Number5989-27-5
Structure
Thumb
Synonyms
SynonymSource
(+)-(4R)-Limonenebiospider
(+)-(r)-limonenebiospider
(+)-1,8-para-Menthadienebiospider
(+)-4-Isopropenyl-1-methylcyclohexenebiospider
(+)-carvenebiospider
(+)-limonenebiospider
(+)-p-Mentha-1,8-dienebiospider
(+)-r-limonenebiospider
(4R)-(+)-Limonenebiospider
(4R)-1-methyl-4-(1-methylethenyl)cyclohexenebiospider
(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-enebiospider
(4R)-1-methyl-4-isopropenylcyclohex-1-enebiospider
(4R)-4-isopropenyl-1-methylcyclohexenebiospider
(4R)-Limonenebiospider
(d)-limonenebiospider
(r)-(+)-limonenebiospider
(R)-(+)-p-Mentha-1,8-dienebiospider
(R)-1-methyl-4-(1-methylethenyl)cyclohexenebiospider
(R)-4-Isopropenyl-1-methyl-1-cyclohexenebiospider
(r)-limonenebiospider
(R)-p-Mentha-1,8-dienebiospider
1-Methyl-4-(1-methylethenyl)cyclohexene, (R)-biospider
4betaH-p-mentha-1,8-dienemanual
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-biospider
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-biospider
D-(+)-limonenebiospider
D-1,8-p-Menthadienebiospider
D-limonenbiospider
D-limonenebiospider
d-p-Mentha-1,8-dienebiospider
Dextro-limonenebiospider
p-Mentha-1,8-diene, (R)-(+)-biospider
Predicted PropertiesNot Available
Chemical FormulaC10H16
IUPAC name
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
ClassificationNot classified
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-74.3 oC
Boiling PointBp20 71°DFC
Experimental Water Solubility0.0138 mg/mL at 25 oCMASSALDI,HA & KING,CJ (1973)
Experimental logP4.57LI,J & PURDUE,EM (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +126.8DFC
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 ID389747
ChEMBL IDCHEMBL449062
KEGG Compound IDC06099
Pubchem Compound ID440917
Pubchem Substance IDNot Available
ChEBI ID15382
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04321
CRC / DFC (Dictionary of Food Compounds) IDJFH51-A:JPJ51-C
EAFUS ID2034
Dr. Duke IDD-(+)-LIMONENE|D-LIMONENE|(+)-LIMONENE
BIGG IDNot Available
KNApSAcK IDC00010868
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID5989-27-5
GoodScent IDrw1013771
SuperScent ID440917
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
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
apoptoticDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
differentiatorDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
hypocholesterolemicDUKE
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
litholyticDUKE
nephrotoxic50909 A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals.DUKE
cytochrome-P450-2B1 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.DUKE
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
citrus
  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
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mint
  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
lemon
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
orange
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  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.