(4R)-limonene

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
(4R)-limonene
Accession Number
DB08921
Type
Small Molecule
Groups
Investigational
Description

Limonene is common in cosmetic products. As the main odor constituent of citrus (plant family Rutaceae), D-limonene is used in food manufacturing and some medicines, e.g. as a flavoring to mask the bitter taste of alkaloids, and as a fragrant in perfumery.

Structure
Thumb
Synonyms
  • (+)-(4R)-Limonene
  • (+)-(R)-Limonene
  • (+)-4-isopropenyl-1-methylcyclohexene
  • (+)-Limonene
  • (4R)-1-methyl-4-isopropenylcyclohex-1-ene
  • (4R)-4-isopropenyl-1-methylcyclohexene
  • (R)-(+)-limonene
  • (R)-(+)-p-mentha-1,8-diene
  • (R)-1-methyl-4-(1-methylethenyl)cyclohexene
  • (R)-4-isopropenyl-1-methyl-1-cyclohexene
  • (R)-p-mentha-1,8-diene
  • 4βH-p-mentha-1,8-diene
  • D-(+)-limonene
  • D-Limonen
  • D-limonene
External IDs
FEMA NO. 2633
Categories
UNII
GFD7C86Q1W
CAS number
5989-27-5
Weight
Average: 136.234
Monoisotopic: 136.125200512
Chemical Formula
C10H16
InChI Key
XMGQYMWWDOXHJM-JTQLQIEISA-N
InChI
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1
IUPAC Name
(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
SMILES
CC(=C)[C@@H]1CCC(C)=CC1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0004321
KEGG Drug
D00194
KEGG Compound
C06099
ChemSpider
389747
ChEBI
15382
ChEMBL
CHEMBL449062
Wikipedia
Limonene

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.457 mg/mLALOGPS
logP4.5ALOGPS
logP3.22ChemAxon
logS-2.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.48 m3·mol-1ChemAxon
Polarizability17.55 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0173-9100000000-239928f205c8242a700a
GC-MS Spectrum - EI-BGC-MSsplash10-014l-9100000000-507f7afbc17b7c2556e2
GC-MS Spectrum - EI-BGC-MSsplash10-014l-9100000000-1a0c62c6971532ab6782
Mass Spectrum (Electron Ionization)MSsplash10-014l-9100000000-fbf154446f93ee5019c0
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-6900000000-f7ee4bad43b6ccae0ccb
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00ou-9000000000-51a52c25a98124e179e9
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-9655665d3d36755028cc
MS/MS Spectrum - EI-B (HITACHI RMU-6M) , PositiveLC-MS/MSsplash10-0173-9100000000-239928f205c8242a700a
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-014l-9100000000-bc8708fdb2d1955dce92
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-014l-9100000000-1a0c62c6971532ab6782
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Menthane monoterpenoids
Alternative Parents
Monocyclic monoterpenoids / Branched unsaturated hydrocarbons / Cycloalkenes / Unsaturated aliphatic hydrocarbons
Substituents
P-menthane monoterpenoid / Monocyclic monoterpenoid / Branched unsaturated hydrocarbon / Cycloalkene / Cyclic olefin / Unsaturated aliphatic hydrocarbon / Unsaturated hydrocarbon / Olefin / Hydrocarbon / Aliphatic homomonocyclic compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
limonene (CHEBI:15382) / Menthane monoterpenoids, Cyclic monoterpenes (C06099) / Menthane monoterpenoids (LMPR0102090013)

Drug created on September 03, 2013 14:56 / Updated on November 02, 2018 06:56