Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:34:46 UTC |
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Updated at | 2020-11-18 16:35:09 UTC |
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CannabisDB ID | CDB000004 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Cannabigerol monomethylether |
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Description | Cannabigerol monomethylether is a methoxylated derivative of cannabigerol, which is a phytocannabinoid. Cannabigerol is a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. It is biosynthetically derived from olivetolic acid on which the hydrogen at position 3 is substituted by a geranyl group. It is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Thus, cannabigerol monomethylether can be considered a polyketide, a monoterpenoid and a resorcinol. Cannabigerol is a minor constituent of cannabis (approximately 1 % of dry weight). During growth, most of the cannabigerol present in the plant’s tissues is converted into other cannabinoids, primarily tetrahydrocannabinol (THC) or cannabidiol (CBD) (PMID: 26836472 ). Cannabigerol monomethylether was first reported to be isolated from the japanese “Minamioshihara No.1” domestic variety in 1968 (PMID: 5706840 ). |
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Structure | |
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Synonyms | Not Available |
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Chemical Formula | C22H34O2 |
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Average Molecular Weight | 330.51 |
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Monoisotopic Molecular Weight | 330.2559 |
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IUPAC Name | 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-methoxy-5-pentylphenol |
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Traditional Name | 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-methoxy-5-pentylphenol |
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CAS Registry Number | Not Available |
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SMILES | CCCCCC1=CC(OC)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 |
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InChI Identifier | InChI=1S/C22H34O2/c1-6-7-8-12-19-15-21(23)20(22(16-19)24-5)14-13-18(4)11-9-10-17(2)3/h10,13,15-16,23H,6-9,11-12,14H2,1-5H3/b18-13+ |
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InChI Key | KASVLYINZPAMNS-QGOAFFKASA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. |
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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 | Aromatic monoterpenoids |
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Alternative Parents | |
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Substituents | - Aromatic monoterpenoid
- Methoxyphenol
- Monocyclic monoterpenoid
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Ether
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | Cannabigerol monomethylether, 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 | 13864080 |
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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 | - Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. [PubMed:26836472 ]
- Yamauchi T, Shoyama Y, Matsuo Y, Nishioka I: Cannabigerol monomethyl ether, a new component of hemp. Chem Pharm Bull (Tokyo). 1968 Jun;16(6):1164-5. doi: 10.1248/cpb.16.1164. [PubMed:5706840 ]
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