Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:29:59 UTC |
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Updated at | 2020-11-18 16:35:03 UTC |
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CannabisDB ID | CDB000305 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | allo-Aromadendrene |
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Description | Alloaromadendrene or Aromadendrene belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpe. These 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 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. Aromadendrene is possibly neutral Aromadendrene is a woody tasting compound. Alloaromadendrene is a sesquiterpene found in cannabis plants only in trace amounts (PMID: 6991645 ). In one particular study, Alloaromadendrene is found in the essential oil of indigenous cinnamon. It exhibits antioxidant activity (PMID: 24918691 ). |
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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 | (1aS,4aS,7R,7aR,7bS)-1,1,7-trimethyl-4-methylidene-decahydro-1H-cyclopropa[e]azulene |
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Traditional Name | (1aS,4aS,7R,7aR,7bS)-1,1,7-trimethyl-4-methylidene-octahydro-1aH-cyclopropa[e]azulene |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1CC[C@H]2[C@@H]1[C@H]1[C@H](CCC2=C)C1(C)C |
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InChI Identifier | InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10-14H,1,5-8H2,2-4H3/t10-,11-,12+,13-,14-/m1/s1 |
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InChI Key | ITYNGVSTWVVPIC-RKQHYHRCSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane 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 | 5,10-cycloaromadendrane sesquiterpenoids |
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Alternative Parents | |
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Substituents | - 5,10-cycloaromadendrane sesquiterpenoid
- Guaiane 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 | Not Available |
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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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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 ]
- Yu CW, Li WH, Hsu FL, Yen PL, Chang ST, Liao VH: Essential oil alloaromadendrene from mixed-type Cinnamomum osmophloeum leaves prolongs the lifespan in Caenorhabditis elegans. J Agric Food Chem. 2014 Jul 2;62(26):6159-65. doi: 10.1021/jf500417y. Epub 2014 Jun 23. [PubMed:24918691 ]
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