| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:37:47 UTC |
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| Updated at | 2020-11-18 16:35:11 UTC |
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| CannabisDB ID | CDB000454 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | alpha-Eudesmol |
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| Description | Alpha-eudesmol (α-eudesmol) is a member of the class of compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquitepenes 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. Alpha-eudesmol is practically insoluble in water but soluble in organic solvents such as methanol, ethanol and ethyl acetate. Alpha-eudesmol can be found in orange, mint, wild celery, ginger, and Cannabis sativa (PMID: 31816756 ; PMID:18242187 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (2R,4AR,8ar)-1,2,3,4,4a,5,6,8a-octahydro-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol | ChEBI | | (2R,4AR,8ar)-1,2,3,4,4a,5,6,8a-octahydro-a,a,4a,8-tetramethyl-2-naphthalenemethanol | Generator | | (2R,4AR,8ar)-1,2,3,4,4a,5,6,8a-octahydro-α,α,4a,8-tetramethyl-2-naphthalenemethanol | Generator | | a-Eudesmol | Generator | | Α-eudesmol | Generator | | 1,2,3,4,4a,5,6,8a-Octahydro-alpha,alpha,4a,8-tetramethyl-(2R-(2alpha,4aalpha,8abeta))-2-naphthalenemethanol | MeSH |
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| Chemical Formula | C15H26O |
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| Average Molecular Weight | 222.37 |
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| Monoisotopic Molecular Weight | 222.1984 |
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| IUPAC Name | 2-[(2R,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]propan-2-ol |
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| Traditional Name | α-eudesmol |
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| CAS Registry Number | 473-16-5 |
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| SMILES | CC1=CCC[C@]2(C)CC[C@H](C[C@@H]12)C(C)(C)O |
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| InChI Identifier | InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h6,12-13,16H,5,7-10H2,1-4H3/t12-,13+,15-/m1/s1 |
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| InChI Key | FCSRUSQUAVXUKK-VNHYZAJKSA-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
- Tertiary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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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| 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 ]
- 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 ]
- Yu F, Harada H, Yamasaki K, Okamoto S, Hirase S, Tanaka Y, Misawa N, Utsumi R: Isolation and functional characterization of a beta-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith. FEBS Lett. 2008 Mar 5;582(5):565-72. doi: 10.1016/j.febslet.2008.01.020. Epub 2008 Jan 31. [PubMed:18242187 ]
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