| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-18 23:23:40 UTC |
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| Updated at | 2020-12-07 19:07:02 UTC |
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| CannabisDB ID | CDB000070 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Fenchone |
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| Description | Fenchone belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, fenchone is an isoprenoid lipid molecule. Fenchone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Fenchone is a colorless oily liquid with a bitter, camphor, and cedar leaf taste. Fenchone occurs in fennels (https://doi.org/10.1111/j.2042-7158.1968.tb09783.x), rosemaries, and star anises making fenchone a potential biomarker for the consumption of these foods. Fenchone was detected in the fresh bud of the cannabis plant (PMID: 8984153 ). Fenchone is used as a flavor in foods such as candy and baked goods and to add scents to soaps, detergents, perfumes and lotions. It also an insect repellent. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (-)-Fenchone | ChEBI | | (1R)-(-)-Fenchone | ChEBI | | (1R)-Fenchone | ChEBI | | (1R,4S)-(-)-Fenchone | ChEBI | | (1R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one | ChEBI | | 1,3,3-Trimethyl-2-norbornanone | MeSH | | Fenchone | MeSH | | Fenchone, (1R)-isomer | MeSH | | Fenchone, (+-)-isomer | MeSH | | Fenchone, (1S)-isomer | MeSH | | (R)-(-)-Fenchone | PhytoBank | | (R)-Fenchone | PhytoBank | | L-(-)-Fenchone | PhytoBank | | l-Fenchone | PhytoBank | | 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one | PhytoBank | | (±)-Fenchone | PhytoBank | | 1,3,3-Trimethylnorcamphor | PhytoBank | | dl-Fenchone | PhytoBank |
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| Chemical Formula | C10H16O |
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| Average Molecular Weight | 152.24 |
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| Monoisotopic Molecular Weight | 152.1201 |
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| IUPAC Name | (1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one |
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| Traditional Name | fenchone, (+-)- |
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| CAS Registry Number | 7787-20-4 |
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| SMILES | CC1(C)[C@H]2CC[C@](C)(C2)C1=O |
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| InChI Identifier | InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1 |
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| InChI Key | LHXDLQBQYFFVNW-OIBJUYFYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. |
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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 | Monoterpenoids |
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| Direct Parent | Bicyclic monoterpenoids |
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| Alternative Parents | |
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| Substituents | - Fenchane monoterpenoid
- Bicyclic monoterpenoid
- Ketone
- 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 | |
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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 | 6.1 °C | Wikipedia | | Boiling Point | 193.5 °C | Wikipedia | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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