| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-08-13 10:44:29 -0600 |
| Update Date |
2013-02-08 11:23:49 -0700 |
| HMDB ID |
HMDB04321 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| 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 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (+)-(4R)-Limonene
- (+)-(R)-Limonene
|
| Chemical Formula |
C10H16 |
| Average Molecular Weight |
136.234 |
| Monoisotopic Molecular Weight |
136.125200512 |
| IUPAC Name |
(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene |
| Traditional IUPAC Name |
(+)-limonene |
| CAS Registry Number |
5989-27-5 |
| SMILES |
CC(=C)[C@@H]1CCC(C)=CC1 |
| InChI Identifier |
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1 |
| InChI Key |
XMGQYMWWDOXHJM-JTQLQIEISA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Prenol Lipids |
| Sub Class |
Monoterpenes |
| Other Descriptors |
- Aliphatic Homomonocyclic Compounds
- Menthane monoterpenoids(KEGG)
- Monoterpenes
- Terpenoids(KEGG)
- a limonene(Cyc)
- monoterpene(ChEBI)
|
| Substituents |
|
| Direct Parent |
Monocyclic Monoterpenes |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Component of Monoterpenoid biosynthesis
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
- Extracellular
- Membrane (predicted from logP)
|
| Physical Properties |
|---|
| State |
Liquid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
-74.3 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
0.0138 mg/mL at 25 °C |
Not Available |
| LogP |
4.57 |
LI,J & PURDUE,EM (1995) |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Extracellular
- Membrane (predicted from logP)
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB014297 |
| KNApSAcK ID |
C00010868 |
| Chemspider ID |
389747 |
| KEGG Compound ID |
C06099 |
| BioCyc ID |
-R-LIMONENE |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB04321 |
| Metagene Link |
HMDB04321 |
| METLIN ID |
7051 |
| PubChem Compound |
440917 |
| PDB ID |
Not Available |
| ChEBI ID |
15382 |
| References |
|---|
| 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. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
Not Available |
