Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:39:33 UTC |
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Updated at | 2020-12-07 19:07:27 UTC |
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CannabisDB ID | CDB000485 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | (1R)-(+)-trans-isolimonene |
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Description | (1R)-(+)-Trans-Isolimonene 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. 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 plant cell 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. (1R) -(+)-trans-isolimonene is possibly neutral and it is one of the terpenes that are known in cannabis plant (PMID: 25454145 ). It was also identified in the essential oil from Salvia sharifii (7.0% relative to total oil constituents) (DOI: 10.1080/0972060X.2014.895684) and Thuja orientalis (1716.31 mg/L from wild leaves, 753.10 mg/L from planted leaves) (DOI: 10.1080/0972060X.2019.1689177). A study has shown that (1R) -(+)-trans-isolimonene has no antibacterial and antifungal effects (PMID: 8693045 ). |
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Structure | |
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Synonyms | Not Available |
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Chemical Formula | C10H16 |
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Average Molecular Weight | 136.23 |
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Monoisotopic Molecular Weight | 136.1252 |
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IUPAC Name | (3R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-1-ene |
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Traditional Name | (3R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-1-ene |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1CC[C@H](C=C1)C(C)=C |
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InChI Identifier | InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,9-10H,1,5,7H2,2-3H3/t9-,10-/m0/s1 |
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InChI Key | TWCNAXRPQBLSNO-UWVGGRQHSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Menthane monoterpenoids |
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Alternative Parents | |
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Substituents | - P-menthane monoterpenoid
- Monocyclic monoterpenoid
- Branched unsaturated hydrocarbon
- Cycloalkene
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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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 | Type | Description | Splash Key | View |
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Predicted GC-MS | (1R)-(+)-trans-isolimonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-006x-9200000000-c60a535fd9fd31f8b94f | Spectrum | Predicted GC-MS | (1R)-(+)-trans-isolimonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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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 | splash10-000i-1900000000-f24bb5ad7cf8034160c6 | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-9500000000-6ed3371f457ae333b307 | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pvi-9000000000-7ec656f36492872b1039 | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-0572dada5d40eb9ff791 | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-bb631cf743c407b4ac0c | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00ku-4900000000-c3f14c70f20bb1a57944 | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-a013b4ae27f975ab5621 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-db25612f5bfd224c18c6 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-1900000000-c05c7501280e6819847a | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001s-9300000000-bb57834010cb18136682 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-005d-9000000000-6f02b8e50b22243276a1 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-002f-9000000000-66318504608d9be5cee9 | 2021-09-25 | 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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External Links |
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HMDB ID | HMDB0061793 |
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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 | 78790 |
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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 | - Marchini M, Charvoz C, Dujourdy L, Baldovini N, Filippi JJ: Multidimensional analysis of cannabis volatile constituents: identification of 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane as a volatile marker of hashish, the resin of Cannabis sativa L. J Chromatogr A. 2014 Nov 28;1370:200-15. doi: 10.1016/j.chroma.2014.10.045. Epub 2014 Oct 23. [PubMed:25454145 ]
- Naigre R, Kalck P, Roques C, Roux I, Michel G: Comparison of antimicrobial properties of monoterpenes and their carbonylated products. Planta Med. 1996 Jun;62(3):275-7. doi: 10.1055/s-2006-957877. [PubMed:8693045 ]
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