| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:50:29 UTC |
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| Updated at | 2020-12-07 19:07:39 UTC |
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| CannabisDB ID | CDB000674 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Valencene |
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| Description | Valencene belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. Sesquiterpenoids 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. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group from the C-10 to the C-5 position. It is an aroma component of citrus fruits and citrus-derived odorants. It is obtained inexpensively from Valencia oranges. Valencene has also been detected as a volatile compound from cannabis samples (PMID: 26657499 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (1R-(1alpha,7beta,8alpha))-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylvinyl)naphthalene | ChEBI | | ent-7BetaH-eremophila-10(1),11-diene | ChEBI | | (1R-(1a,7b,8a))-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylvinyl)naphthalene | Generator | | (1R-(1Α,7β,8α))-1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylvinyl)naphthalene | Generator | | Valencene | ChEBI | | 4betaH,5alpha-Eremophila-1(10),11-diene | PhytoBank | | 4βH,5α-Eremophila-1(10),11-diene | PhytoBank | | (1R,7R,8aS)-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylethenyl)naphthalene | PhytoBank | | (+)-Valencene | PhytoBank | | Valencen | PhytoBank |
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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 | (3R,4aS,5R)-4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene |
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| Traditional Name | valencene |
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| CAS Registry Number | 4630-07-3 |
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| SMILES | C[C@@H]1CCC=C2CC[C@H](C[C@@]12C)C(C)=C |
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| InChI Identifier | InChI=1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3/t12-,13-,15+/m1/s1 |
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| InChI Key | QEBNYNLSCGVZOH-NFAWXSAZSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. |
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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 | Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Eremophilane 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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| 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 | 123 °C at 11 mmHg | Wikipedia | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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| General References | - 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 ]
- 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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