Back to Compounds

(R)-Limonene (PC000738)

Record Information
Version1.0
Creation date2015-10-09 22:32:20 UTC
Update date2017-01-19 02:36:34 UTC
FoodComEx IDPC000738
FoodDB RecordFDB014297
Chemical Information
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
MOLSDFPDBSMILESInChI
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
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
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP4.57LI,J & PURDUE,EM (1995)
Experimental Water Solubility0.0138 mg/mL at 25 oCMASSALDI,HA & KING,CJ (1973)
Melting Point-74.3 oC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 30 mg
Delivery TimeNot Available
Storage Formliquid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci 6458AE
MetaSci HMDB0004321
Sigma-Aldrich HMDB0004321
Toronto Research Chemicals L461740