| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:52:59 UTC |
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| Updated at | 2020-11-18 16:35:28 UTC |
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| CannabisDB ID | CDB000720 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Humulene oxide |
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| Description | Humulene oxide is the oxidized or epoxide form of alpha-humulene. It is also known as Humulene epoxide I, or as alpha-humulene oxide. Humulene oxide or belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms (one oxygen and two carbon atoms). Humulene oxide is also biochemically classified as a terpenoid or a monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds. Humulene oxide exists as a clear, colorless liquid and essentially insoluble in water. It has a herbal or hoppy odor and is found naturally in a number of spices, including hops, sage, rosemary, oregano, clove, basil and allspice. Humulene oxide is typically found in alcoholic beverages, especially beer, where hops are added. Humulene oxide is a constituent of hops, cannabis and wild ginger (Zingiber zerumbet) and helps give these plants their characteristic herbal, skunky or “hoppy” fragrance. Humulene, the parent compound of humulene oxide, is a naturally occurring substance found in the flowering cone of the hops plant, Humulus lupulus, from which it derives its name. Humulene and humulene oxide are also found in the flowers of related plants such as cannabis (PMID: 6991645 ). The concentration of humulene varies among different varieties of hops and cannabis but can be up to 40% of the essential oil. Multiple epoxides of humulene (such as humulene epoxide I and humulene epoxide II) are produced in the brewing process of beer or in the extraction of cannabis oils. |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C15H24O |
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| Average Molecular Weight | 220.36 |
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| Monoisotopic Molecular Weight | 220.1827 |
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| IUPAC Name | (1S,4Z,7Z,11R)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene |
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| Traditional Name | (1S,4Z,7Z,11R)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene |
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| CAS Registry Number | 19888-33-6 |
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| SMILES | C\C1=C\CC[C@]2(C)O[C@@H]2CC(C)(C)\C=C/C1 |
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| InChI Identifier | InChI=1S/C15H24O/c1-12-7-5-9-14(2,3)11-13-15(4,16-13)10-6-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5-,12-8-/t13-,15+/m1/s1 |
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| InChI Key | RKQDKXOBRXTSFS-KDYBSOQRSA-N |
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| Chemical Taxonomy |
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| Classification | Not classified |
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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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