| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:52:21 UTC |
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| Updated at | 2020-12-07 19:07:42 UTC |
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| CannabisDB ID | CDB000709 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Linalool oxide |
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| Description | Linalool oxide belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. The less common form of linalool oxide is based on a six member, pyran-like structure. In addition to being classified ans an oxolane, linalool oxide is also classified as a monoterpene. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Both cis and trans forms of linalool oxide exist. Linalool oxide is a naturally occurring compound derived from linalool. Linalool and linalool oxide are found in more than 200 different species of plants, including many flowers and spice plants including those from Lamiaceae (mint and other herbs), Lauraceae (laurels, cinnamon, rosewood), and Rutaceae (citrus fruits). Linalool oxide has pleasant scent (floral, herbal, earthy or green). The furan-based linalool oxide has a floral character, somewhat reminiscent of lavender, but this is dominated by the profile of black tea. The pyran-based linalool oxide is more obviously floral, with less resemblance to tea. Linalool oxide is an approved food additive (as a flavor or fragrance agent) and can be found in baked goods, soft candy, beverages and frozen dairy products. Linalool oxide is one of the many monoterpenes found in cannabis plants and their essential oils. (PMID: 6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Linalool oxide exhibits clear antinociceptive (pain reduction) and anticonvulsant effects at relatively modest doses (50 mg/kg) in animal studies (PMID: 27622736 ). Approximately 7% of people undergoing patch testing in Europe were found to be allergic to linalool oxide ( PMID: 28960261 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C10H18O2 |
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| Average Molecular Weight | 170.25 |
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| Monoisotopic Molecular Weight | 170.1307 |
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| IUPAC Name | (2S)-6-methyl-2-[(2S)-oxiran-2-yl]hept-5-en-2-ol |
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| Traditional Name | (2S)-6-methyl-2-[(2S)-oxiran-2-yl]hept-5-en-2-ol |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)=CCC[C@](C)(O)[C@@H]1CO1 |
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| InChI Identifier | InChI=1S/C10H18O2/c1-8(2)5-4-6-10(3,11)9-7-12-9/h5,9,11H,4,6-7H2,1-3H3/t9-,10-/m0/s1 |
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| InChI Key | BXOURKNXQXLKRK-UWVGGRQHSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). |
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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 | Tertiary alcohols |
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| Alternative Parents | |
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| Substituents | - Tertiary alcohol
- Oxacycle
- Organoheterocyclic compound
- Ether
- Oxirane
- Dialkyl ether
- Hydrocarbon derivative
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic 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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| Spectra |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Linalool oxide, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available | 2020-06-30 | View Spectrum |
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| NMR | Not Available |
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| Pathways |
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| Pathways | Not Available |
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| Protein Targets |
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| Enzymes | Not Available |
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| Transporters | Not Available |
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| Metal Bindings | Not Available |
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| Receptors | Not Available |
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| Transcriptional Factors | Not Available |
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| Concentrations Data |
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| Not Available |
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| External Links |
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| HMDB ID | Not Available |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | Not Available |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Not Available |
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| METLIN ID | Not Available |
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| PubChem Compound | 92256275 |
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| PDB ID | Not Available |
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| ChEBI ID | Not Available |
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| References |
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| General References | - Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
- Souto-Maior FN, Fonseca DV, Salgado PR, Monte LO, de Sousa DP, de Almeida RN: Antinociceptive and anticonvulsant effects of the monoterpene linalool oxide. Pharm Biol. 2017 Dec;55(1):63-67. doi: 10.1080/13880209.2016.1228682. Epub 2016 Sep 13. [PubMed:27622736 ]
- McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
- Ung CY, White JML, White IR, Banerjee P, McFadden JP: Patch testing with the European baseline series fragrance markers: a 2016 update. Br J Dermatol. 2018 Mar;178(3):776-780. doi: 10.1111/bjd.15949. Epub 2018 Jan 30. [PubMed:28960261 ]
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