| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-18 23:24:42 UTC |
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| Updated at | 2020-11-18 16:34:46 UTC |
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| CannabisDB ID | CDB000098 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Longifolene |
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| Description | Longifolene is a tricyclic sesquiterpene synthesized from isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID: 17467679 ), in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Longifolene is a colorless to yellow clear oily liquid found in the high-boiling fraction of certain pine resins. The name is derived from the pine species, Pinus longifolia, from which it was isolated. It has a woody, medicinal, pine, ambergris flavor with a sweet woody rose medicinal fir needle odor ( Ref:DOI ). It is found in mandarin, artichoke, and star anise fruit and in oils from carrot seeds, hinoki leaf, root and wood and pine needle. Longifolene found in rosemary plants and cannabis plants (PMID: 6991645 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C15H24 |
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| Average Molecular Weight | 204.36 |
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| Monoisotopic Molecular Weight | 204.1878 |
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| IUPAC Name | (1R,2S,7S,9S)-3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0^{2,9}]undecane |
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| Traditional Name | (1R,2S,7S,9S)-3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0^{2,9}]undecane |
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| CAS Registry Number | 475-20-7 |
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| SMILES | C[C@]12CCCC(C)(C)[C@H]3[C@H](CC[C@@H]13)C2=C |
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| InChI Identifier | InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,15-/m1/s1 |
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| InChI Key | PDSNLYSELAIEBU-GUIRCDHDSA-N |
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| Chemical Taxonomy |
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| Classification | Not classified |
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| Ontology |
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Not Available | | 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 | 254 °C at 706 mmHg | Wikipedia | | 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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| External Links | Not Available |
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| References |
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| General References | - Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
- Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. [PubMed:17467679 ]
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