Caryophyllene
| Caryophyllene | |
|---|---|
| File:Beta-Caryophyllen.svg | |
| 4,11,11-trimethyl-8-methylene- bicyclo[7.2.0]undec-4-ene | |
| Other names β-Caryophyllene; trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 87-44-5 
|
| PubChem | 5281515 |
| ChemSpider | 4444848 |
| SMILES | Script error: No such module "collapsible list". |
| InChI | Script error: No such module "collapsible list". |
| InChI key | NPNUFJAVOOONJE-GFUGXAQUBC |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C15H24 |
| Molar mass | 204.36 g/mol |
| Density | 0.9052 g/cm3 |
| Boiling point |
262-264 °C; 129-130 °C (14 mm Hg) |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Caryophyllene (pronounced /ˌkæri.ɵfɪˈliːn/), or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves)[1], the essential oil of hemp Cannabis sativa[2], rosemary Rosmarinus oficinalis[3], and hops[4]. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, a rarity in nature.
Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. Recently, in a study conducted by Jürg Gertsch et al. from the Swiss Federal Institute of Technology (ETH Zurich), beta-caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.[2] Since the widespread plant natural product beta-caryophyllene is an FDA approved food additive and ingested daily with food it is the first dietary cannabinoid. Whether this compound is able to modulate inflammatory processes in humans via the endocannabinoid system is yet unknown. Beta-caryophyllene does not bind to the centrally expressed cannabinoid receptor type-1 (CB1) and therefore does not exert psychomimetic effects.
The first total synthesis of caryophyllene in 1964 by E.J. Corey was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time.[5]
Natural sources
The approximate quantity of caryophyllene in the essential oil of each source is given in square brackets ([ ]):
- Cannabis, hemp, marijuana (Cannabis sativa)[2] [3.8–37.5% of cannabis flower essential oil][6]
- Black Caraway (Carum nigrum) [7.8%][7]
- Cloves (Syzygium aromaticum)[1] [3.56% of clove bud essential oil][8]
- Hops (Humulus lupulus)[9] [5.1–14.5%][10]
- Basil (Ocimum spp.)[11] [5.3–10.5% O. gratissimum; 4.0–19.8% O. micranthum][12]
- Oregano (Origanum vulgare)[13] [4.9%][14]
- Black pepper (Piper nigrum) [7.29%][15]
- West African Pepper (Piper guineense) [57.59% (black); 51.75% (white)][15]
- Rosemary (Rosmarinus officinalis)[3] [0.1–8.3%][16]
- True cinnamon (Cinnamomum zeylanicum) [6.9–11.1%][17]
- Malabathrum (Cinnamomum tamala) [25.3%][18]
Compendial status
Notes and references
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- "Some Proof that Marijuana is a Powerful Medicine", Aaron Rowe, Wired Magazine, June 29, 2008de:Caryophyllene
it:Beta-cariofillene nl:Caryofylleen
ru:Кариофиллен- ↑ 1.0 1.1 Ghelardini C, Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A (2001). "Local anaesthetic activity of beta-caryophyllene". Farmaco. 56 (5-7): 387–9. doi:10.1016/S0014-827X(01)01092-8. PMID 11482764.
- ↑ 2.0 2.1 2.2 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Glenn Tinseth, "Hop Aroma and Flavor", January/February 1993, Brewing Techniques. <http://realbeer.com/hops/aroma.html> Accessed July 21, 2010.
- ↑ Corey EJ, Mitra RB, Uda H (1964). "Total Synthesis of d,l-Caryophyllene and d,l-Isocaryophyllene". Journal of the American Chemical Society. 86 (3): 485–492. doi:10.1021/ja01057a040.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Bernotienë, Genovaitë; Nivinskienë, Ona; Butkienë, Rita; Mockutë, Danutë (2004). "Chemical composition of essential oils of hops (Humulus lupulus L.) growing wild in Auktaitija" (PDF). Chemija. 2. Vilnius, Lithuania: Lithuanian Academy of Sciences. 4: 31–36. ISSN 0235-7216. Retrieved September 6, 2010. C1 control character in
|title=at position 88 (help) - ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Silva, Maria Goretti de Vasconcelos; Matos, Francisco José de Abreu; Lopes, Paulo Roberto Oliveira; Silva, Fábio Oliveira; Holanda, Márcio Tavares (August 2, 2004). Cragg, Gordon M.; Bolzani, Vanderlan S.; Rao, G. S. R. Subba, eds. "Composition of essential oils from three Ocimum species obtained by steam and microwave distillation and supercritical CO2 extraction" (PDF). Arkivoc. ARKAT USA, Inc. 2004 (vi): 66–71. ISSN 1424-6376. Retrieved September 6, 2010.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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- ↑ 15.0 15.1 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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- ↑ Kaul PN, Bhattacharya AK, Rao BRR; et al. (2003). "Volatile constituents of essential oils isolated from different parts of cinnamon (Cinnamomum zeylanicum Blume)". Journal of the Science of Food and Agriculture. 83 (1): 53–55. doi:10.1002/jsfa.1277.
- ↑ Ahmed A, Choudhary MI, Farooq A; et al. (2000). "Essential oil constituents of the spice Cinnamomum tamala (Ham.) Nees & Eberm". Flavour and Fragrance Journal. 15 (6): 388–390. doi:10.1002/1099-1026(200011/12)15:6<388::AID-FFJ928>3.0.CO;2-F.
- ↑ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". Retrieved 29 June 2009.
- ↑ Therapeutic Goods Administration. "Chemical substances" (PDF). Retrieved 29 June 2009.
