| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:30:08 UTC |
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| Updated at | 2020-11-18 16:35:03 UTC |
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| CannabisDB ID | CDB000308 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | alpha-Caryophyllene alcohol |
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| Description | Alpha-Caryophyllene alcohol also called alpha-Caryophyllenol is a derivative of alpha-Caryophyllene. It belongs to the class of organic compounds known as sesquiterpenoids. It is formally classified as a polycyclic hydrocarbon although it is biochemically a bicyclic sesquiterpenoid as it is synthesized via multiple isoprene units. 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-erythritol-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. Alpha-Caryophyllene alcohol exists as a white, crystalline powder. It is a neutral, hydrophobic molecule that is insoluble in water. Alpha-Caryophyllene is an approved food additive and has a woody, spicy or earthy aroma. It is a naturally occurring substance found in a number of foods or plants including black pepper, allspice and guava fruit. It was first synthesized by E.J. Corey in 1964 ( Ref:DOI ). Alpha-Caryophyllene alcohol is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645 ) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. |
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| Structure | |
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| Synonyms | Not Available |
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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 | (1R,2S,6R,7S,11R)-1,4,4,7-tetramethyltricyclo[5.3.1.0^{2,6}]undecan-11-ol |
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| Traditional Name | (1R,2S,6R,7S,11R)-1,4,4,7-tetramethyltricyclo[5.3.1.0^{2,6}]undecan-11-ol |
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| CAS Registry Number | 4586-22-5 |
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| SMILES | CC1(C)C[C@H]2[C@@H](C1)[C@]1(C)CCC[C@@]2(C)[C@@H]1O |
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| InChI Identifier | InChI=1S/C15H26O/c1-13(2)8-10-11(9-13)15(4)7-5-6-14(10,3)12(15)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14+,15- |
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| InChI Key | MJYUBUQHKCAJQR-LYOXDTQASA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Alcohols and polyols |
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| Direct Parent | Cyclic alcohols and derivatives |
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| Alternative Parents | |
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| Substituents | - Cyclic alcohol
- Secondary alcohol
- Hydrocarbon derivative
- 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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