| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:30:39 UTC |
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| Updated at | 2020-11-18 16:35:04 UTC |
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| CannabisDB ID | CDB000318 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | aplha-selinene |
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| Description | Alpha-Selinene (α-selinene) also known as selinene, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). 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. α-Selinene is one of many terpenes that can be found in cannabis plants ( PMID: 31816756 ), together with the other three known Selinene isomers, β-, γ-, and δ- selinene. Selinenes have been detected in a variety of plant species, with α- and β-selinene being the most frequent, while γ-Selinene and δ-selinene are less common. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (2R-(2alpha,4Aalpha,8abeta))-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethenyl)naphthalene | ChEBI | | 2-Isopropenyl-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene | ChEBI | | Eudesma-3,11-diene | ChEBI | | (2R-(2a,4Aalpha,8abeta))-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethenyl)naphthalene | Generator | | (2R-(2Α,4aalpha,8abeta))-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethenyl)naphthalene | Generator | | a-Selinene | Generator | | Α-selinene | Generator |
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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 | (2R,4aR,8aR)-4a,8-dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene |
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| Traditional Name | α-selinene |
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| CAS Registry Number | 473-13-2 |
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| SMILES | CC(=C)[C@@H]1CC[C@@]2(C)CCC=C(C)[C@@H]2C1 |
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| InChI Identifier | InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h6,13-14H,1,5,7-10H2,2-4H3/t13-,14+,15-/m1/s1 |
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| InChI Key | OZQAPQSEYFAMCY-QLFBSQMISA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. |
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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 | Sesquiterpenoids |
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| Direct Parent | Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
- Branched unsaturated hydrocarbon
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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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 | 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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| Alien Dawg | Detected and Quantified | 0.27 mg/g dry wt | | details | | Alien Dawg (Indica dominant) | Detected and Quantified | 0.22 +/- 0.02 mg/g dry wt | | details | | Gabriola | Detected and Quantified | 0.35 mg/g dry wt | | details | | Island Honey | Detected and Quantified | 0.18 mg/g dry wt | | details | | Quadra | Detected and Quantified | 0.24 mg/g dry wt | | details | | Sensi Star | Detected and Quantified | 0.12 mg/g dry wt | | details | | Sensi Star (Pure Indica) | Detected and Quantified | 0.09 +/- 0.00 mg/g dry wt | | details |
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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 ]
- Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
- Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
- Delgado-Povedano MM, Sanchez-Carnerero Callado C, Priego-Capote F, Ferreiro-Vera C: Untargeted characterization of extracts from Cannabis sativa L. cultivars by gas and liquid chromatography coupled to mass spectrometry in high resolution mode. Talanta. 2020 Feb 1;208:120384. doi: 10.1016/j.talanta.2019.120384. Epub 2019 Sep 25. [PubMed:31816756 ]
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