| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:47:02 UTC |
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| Updated at | 2020-12-07 19:07:35 UTC |
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| CannabisDB ID | CDB000620 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Limonene dioxide |
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| Description | Limonene dioxide or Limonene diepoxide belongs to the class of organic compounds known as menthane monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Menthanes 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 an isopropyl 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. Limonene dioxide is the di-epoxylated derivative of limonene. Limonene is a colorless liquid and is the major component in the oil of citrus fruit peels. Limonene is common as a dietary supplement and as a fragrance ingredient for cosmetics products. Limonene dioxide has been detected as a volatile component in cannabis plant samples (PMID: 26657499 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C10H16O2 |
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| Average Molecular Weight | 168.24 |
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| Monoisotopic Molecular Weight | 168.115 |
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| IUPAC Name | (1S,4S,6R)-1-methyl-4-[(2S)-2-methyloxiran-2-yl]-7-oxabicyclo[4.1.0]heptane |
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| Traditional Name | (1S,4S,6R)-1-methyl-4-[(2S)-2-methyloxiran-2-yl]-7-oxabicyclo[4.1.0]heptane |
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| CAS Registry Number | 96-08-2 |
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| SMILES | C[C@@]1(CO1)[C@H]1CC[C@]2(C)O[C@@H]2C1 |
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| InChI Identifier | InChI=1S/C10H16O2/c1-9-4-3-7(5-8(9)12-9)10(2)6-11-10/h7-8H,3-6H2,1-2H3/t7-,8+,9-,10+/m0/s1 |
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| InChI Key | RBHIUNHSNSQJNG-QCLAVDOMSA-N |
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| Chemical Taxonomy |
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| Classification | Not classified |
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| Ontology |
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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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| Spectra |
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| EI-MS/GC-MS | Not Available |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available | 2020-06-30 | View Spectrum |
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| NMR | Not Available |
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| Pathways |
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| Pathways | Not Available |
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| Protein Targets |
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| Enzymes | Not Available |
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| Transporters | Not Available |
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| Metal Bindings | Not Available |
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| Receptors | Not Available |
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| Transcriptional Factors | Not Available |
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| Concentrations Data |
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| Not Available |
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| External Links |
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| HMDB ID | Not Available |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | Not Available |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Not Available |
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| METLIN ID | Not Available |
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| PubChem Compound | 121492667 |
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| PDB ID | Not Available |
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| ChEBI ID | Not Available |
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| References |
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| General References | - Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
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