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Bovine Metabolome Database



Showing metabocard for (+)-Limonene (BMDB04321)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2006-08-13 17:44:29
Update Date 2009-05-27 14:28:59
Accession Number BMDB04321
Common Name (+)-Limonene
Description Limonene is a monoterpene with a clear colourless liquid at room temperature, a naturally occurring chemical which is the major component in oil of oranges. Limonene is widely used as a flavor and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). Limonene is a botanical (plant-derived) solvent of low toxicity. Mild skin irritation may occur from exposure to limonene and oxidation products of limonene may produce dermal sensitization, and may have irritative and bronchoconstrictive airway effects; however, data are scant and more studies are required. Limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to limonene causes a significant incidence of renal tubular tumors exclusively in male rats. Limonene is one of the active components of dietary phytochemicals that appears to be protective against cancer. (PMID: 16563357, 15499193, 15325315, 2024047)
Synonyms
  1. (+)-(4R)-Limonene
  2. (+)-(R)-Limonene
Chemical IUPAC Name (4R)-1-methyl-4-prop-1-en-2-yl-cyclohexene
Chemical Formula C10H16
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Miscellanous
Class
  • Alkanes and Alkenes
Sub Class
  • Medium chain alkenes
Family
  • Mammalian_Metabolite
Species
  • alkene
Biofunction
  • Component of Monoterpenoid biosynthesis
Application
Source
  • Exogenous
Average Molecular Weight 136.234
Monoisotopic Molecular Weight 136.125198
Isomeric SMILES CC(=C)[C@@H]1CCC(C)=CC1
Canonical SMILES CC(=C)C1CCC(C)=CC1
KEGG Compound ID C06099 Link Image
BioCyc ID -R-LIMONENE Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 7051 Link Image
PubChem Compound 440917 Link Image
PubChem Substance 8145134 Link Image
ChEBI ID 15382 Link Image
CAS Registry Number 5989-27-5
InChI Identifier InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1
Synthesis Reference Sakane, Soichi; Fujiwara, Junya; Maruoka, Keiji; Yamamoto, Hisashi. Chiral leaving group: asymmetric synthesis of limonene and bisabolene. Tetrahedron (1986), 42(8), 2193-2201.
Melting Point (Experimental) -74.3 oC
Experimental Water Solubility 0.0138 mg/mL at 25 oC [MASSALDI,HA & KING,CJ (1973)] Source: PhysProp
Predicted Water Solubility 0.45700002 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Liquid
Experimental LogP/Hydrophobicity 4.57 [LI,J & PURDUE,EM (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 4.50 [Predicted by ALOGPS]; 3.7 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
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2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available