Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:52:43 UTC |
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Updated at | 2020-11-18 16:35:27 UTC |
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CannabisDB ID | CDB000715 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | 1,8-Menthadien-4-ol |
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Description | 1,8-Menthadien-4-ol or p-Mentha-1,8-dien-4-ol or Limonene-4-ol belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 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. 1,8-Menthadien-4-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). It exists as a pale, clear liquid and has a peppery, spicy aroma. p-Mentha-1,8-dien-4-ol has been detected, but not quantified in, several different foods, such as blackcurrants, caraway, citrus, pepper (spice), and spearmints. This could make p-mentha-1,8-dien-4-ol a potential biomarker for the consumption of these foods. p-mentha-1,8-dien-4-ol is also used as a phermone for pine bark beetles. 1,8-Menthadien-4-ol is one of the terpenoids that present only in traces in cannabis plants (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. |
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Structure | |
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Synonyms | Not Available |
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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)-4-methyl-1-(prop-1-en-2-yl)cyclohex-3-en-1-ol |
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Traditional Name | (1R)-4-methyl-1-(prop-1-en-2-yl)cyclohex-3-en-1-ol |
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CAS Registry Number | 3419-02-1 |
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SMILES | CC(=C)[C@@]1(O)CCC(C)=CC1 |
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InChI Identifier | InChI=1S/C10H16O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,11H,1,5-7H2,2-3H3/t10-/m0/s1 |
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InChI Key | OVKDFILSBMEKLT-JTQLQIEISA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. |
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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 | Menthane monoterpenoids |
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Alternative Parents | |
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Substituents | - P-menthane monoterpenoid
- Monocyclic monoterpenoid
- Tertiary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Role | Indirect biological role: |
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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 | 1,8-Menthadien-4-ol, 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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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 | 16059268 |
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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 | - McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
- 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 ]
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