| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:44:52 UTC |
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| Updated at | 2020-12-07 19:07:32 UTC |
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| CannabisDB ID | CDB000581 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Cedryl acetate |
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| Description | Cedryl acetate belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiterpenoids with a structure based on the cedrane or the isocedrane skeleton. Isocedrane is a rearranged cedrane arising from the migration of a methyl group from the position 6 to the position 4. Sesquiterpenoides 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. Cedryl acetate is the acetylated derivative of cedrol. Cedrol is a tricyclic molecule based on a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety, bearing a tertiary hydroxyl group. Cedryl acetate is a pale-yellow viscous liquid to solid and has a sharp dry woody odor. Cedrol has been reported to show antiseptic, anti-inflammatory, antispasmodic, tonic, astringent, diuretic, sedative, insecticidal, and antifungal activities (PMID 25343299 ). Additionally, cedrol seems to be a potent attractant for female mosquitos during oviposition, which could make cedrol useful in the design of bait traps (PMID: 25885703 ). Cedrol acetate has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| Cedryl acetic acid | Generator |
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| Chemical Formula | C17H28O2 |
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| Average Molecular Weight | 264.41 |
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| Monoisotopic Molecular Weight | 264.2089 |
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| IUPAC Name | (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undecan-8-yl acetate |
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| Traditional Name | (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undecan-8-yl acetate |
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| CAS Registry Number | 77-54-3 |
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| SMILES | C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC[C@@]3(C)OC(C)=O |
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| InChI Identifier | InChI=1S/C17H28O2/c1-11-6-7-13-15(3,4)14-10-17(11,13)9-8-16(14,5)19-12(2)18/h11,13-14H,6-10H2,1-5H3/t11-,13+,14-,16-,17+/m1/s1 |
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| InChI Key | HQKQRXZEXPXXIG-DTWJZALFSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. |
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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 | Cedrane and isocedrane sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Cedrane sesquiterpenoid
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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| 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 | 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 | - 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 ]
- Jeong HU, Kwon SS, Kong TY, Kim JH, Lee HS: Inhibitory effects of cedrol, beta-cedrene, and thujopsene on cytochrome P450 enzyme activities in human liver microsomes. J Toxicol Environ Health A. 2014;77(22-24):1522-32. doi: 10.1080/15287394.2014.955906. [PubMed:25343299 ]
- Lindh JM, Okal MN, Herrera-Varela M, Borg-Karlson AK, Torto B, Lindsay SW, Fillinger U: Discovery of an oviposition attractant for gravid malaria vectors of the Anopheles gambiae species complex. Malar J. 2015 Mar 20;14:119. doi: 10.1186/s12936-015-0636-0. [PubMed:25885703 ]
- 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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