| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:44:54 UTC |
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| Updated at | 2020-11-18 16:35:18 UTC |
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| CannabisDB ID | CDB000582 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | cis-2-pinanol |
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| Description | Cis-2-Pinanol is an organic compound and a derivative of pinane, on which a hydrogen atom has been replaced by a hydroxyl group on position C-2. Cis-2-Pinanol with the molecular formula C10H18O is biochemically a bicyclic monoterpenenoid. 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. 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. Cis-2-Pinanol is one of two isomers of 2-Pinanol. Cis-2-Pinanol is a colorless crystal with a camphor-like odor. It is produced industrially by the catalytic hydrogenation of 2-pinane hydroperoxide. Cis-2-Pinanol can also be obtained directly from pinane by air oxidation in the presence of alkalis, such as sodium hydroxide, at 80 – 100 °C ( Ref:DOI ). Cis-2-pinanol has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C10H18O |
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| Average Molecular Weight | 154.25 |
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| Monoisotopic Molecular Weight | 154.1358 |
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| IUPAC Name | (1R,2S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol |
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| Traditional Name | (1R,2S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol |
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| CAS Registry Number | 4948-28-1 |
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| SMILES | CC1(C)[C@@H]2C[C@H]1[C@@](C)(O)CC2 |
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| InChI Identifier | InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10-/m0/s1 |
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| InChI Key | YYWZKGZIIKPPJZ-XKSSXDPKSA-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 | - Pinane monoterpenoid
- Bicyclic monoterpenoid
- Tertiary alcohol
- Cyclic 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 | 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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| Spectra |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | cis-2-pinanol, 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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| Alien Dawg | Detected and Quantified | 0.08 mg/g dry wt | | details | | Gabriola | Detected and Quantified | 0.44 mg/g dry wt | | details | | Island Honey | Detected and Quantified | 0.02 mg/g dry wt | | details | | Quadra | Detected and Quantified | 0.39 mg/g dry wt | | details | | Sensi Star | Detected and Quantified | 0.04 mg/g dry wt | | details | | Tangerine Dream | Detected and Quantified | 0.04 mg/g dry wt | | details |
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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 | 6428289 |
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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 | - Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
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