| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:52:35 UTC |
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| Updated at | 2020-12-07 19:07:42 UTC |
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| CannabisDB ID | CDB000712 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | trans-beta-Caryophyllene |
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| Description | Trans-caryophyllene or beta-caryophyllene (BCP), also known as just caryophelene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol (PMID: 7640522 ). However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-caryophyllene is considered to be an isoprenoid lipid molecule. Beta-caryophyllene is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. There are several isomers of caryophyllene including beta-caryophyllene (with cis and trans double bonds), alpha-caryophyllene (also known as alpha humulene) and gamma-caryophyllene or isocaryophyllene (the cis double-bond isomer). The first total synthesis of beta-caryophyllene was done in 1964 by E. J. Corey and was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time ( Ref:DOI ). Beta-caryophyllene exists as a pale, clear liquid and has a sweet, woody or spicy odor along with a clove, peppery or woody taste. Beta-caryophyllene can be used in cosmetics as a perfuming agent or in food as a flavoring agent. β-Caryophyllene is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa (PMID: 29783790 ), rosemary, and hops. Trans-beta-Caryophyllene is a sweet and dry tasting compound that can be found in a number of food items such as allspice, figs, pot marjoram, and roman camomile, which makes beta-caryophyllene a potential biomarker for the consumption of these food products. Beta-caryophyllene is one of the chemical compounds that contributes to the aroma of black pepper (PMID: 12462618 ). Beta-caryophyllene is the most common sesquiterpene in cannabis plants and exhibits anti-inflammatory, cytoprotective (gastric mucosa), and antimalarial activities. Beta-caryophyllene is a functional non-psychoactive CB2 receptor agonist (PMID: 26965491 ) and has shown analgesic, anti-inflammatory, neuroprotective, anti-depressive, anxiolytic and anti-nephtotoxicity effects in a number of studies (PMID: 28368293 ). More recently Beta caryophyllene has been shown to inhibit microglial cells, CD4+ and CD8+ T lymphocytes, as well as protein expression of pro-inflammatory cytokines in a murine model of multiple sclerosis. This led to a suppression of motor paralysis and neuroinflammation in the MS-affected animals (PMID: 28368293 ). | Read more...
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C15H24 |
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| Average Molecular Weight | 204.36 |
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| Monoisotopic Molecular Weight | 204.1878 |
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| IUPAC Name | (1S,4Z,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene |
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| Traditional Name | (1S,4Z,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene |
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| CAS Registry Number | 10579-93-8 |
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| SMILES | C\C1=C\CCC(=C)[C@@H]2CC(C)(C)[C@H]2CC1 |
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| InChI Identifier | InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14-/m0/s1 |
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| InChI Key | NPNUFJAVOOONJE-BJLYVFBQSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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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 | Sesquiterpenoids |
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| Direct Parent | Sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Caryophyllane sesquiterpenoid
- Sesquiterpenoid
- Branched unsaturated hydrocarbon
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- 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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| 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 | Not Available |
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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 | |
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| Transcriptional Factors | Not Available |
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| Concentrations Data |
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| Alien Dawg | Detected and Quantified | 1.86 mg/g dry wt | | details | | Alien Dawg (Indica dominant) | Detected and Quantified | 2.24 +/- 0.05 mg/g dry wt | | details | | Gabriola | Detected and Quantified | 2.37 mg/g dry wt | | details | | Island Honey | Detected and Quantified | 1.32 mg/g dry wt | | details | | Quadra | Detected and Quantified | 1.02 mg/g dry wt | | details | | Sensi Star | Detected and Quantified | 0.78 mg/g dry wt | | details | | Sensi Star (Pure Indica) | Detected and Quantified | 0.68 +/- 0.01 mg/g dry wt | | details | | Tangerine Dream | Detected and Quantified | 0.85 mg/g dry wt | | details | | Tangerine Dream (Sativa dominant) | Detected and Quantified | 0.80 +/- 0.03 mg/g dry wt | | details |
| Show more...
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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 | 5452236 |
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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 ]
- Pavlovic R, Nenna G, Calvi L, Panseri S, Borgonovo G, Giupponi L, Cannazza G, Giorgi A: Quality Traits of "Cannabidiol Oils": Cannabinoids Content, Terpene Fingerprint and Oxidation Stability of European Commercially Available Preparations. Molecules. 2018 May 20;23(5). pii: molecules23051230. doi: 10.3390/molecules23051230. [PubMed:29783790 ]
- Jirovetz L, Buchbauer G, Ngassoum MB, Geissler M: Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry. J Chromatogr A. 2002 Nov 8;976(1-2):265-75. doi: 10.1016/s0021-9673(02)00376-x. [PubMed:12462618 ]
- Sharma C, Al Kaabi JM, Nurulain SM, Goyal SN, Kamal MA, Ojha S: Polypharmacological Properties and Therapeutic Potential of beta-Caryophyllene: A Dietary Phytocannabinoid of Pharmaceutical Promise. Curr Pharm Des. 2016;22(21):3237-64. doi: 10.2174/1381612822666160311115226. [PubMed:26965491 ]
- Alberti TB, Barbosa WL, Vieira JL, Raposo NR, Dutra RC: (-)-beta-Caryophyllene, a CB2 Receptor-Selective Phytocannabinoid, Suppresses Motor Paralysis and Neuroinflammation in a Murine Model of Multiple Sclerosis. Int J Mol Sci. 2017 Apr 1;18(4). pii: ijms18040691. doi: 10.3390/ijms18040691. [PubMed:28368293 ]
- 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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