Caryophyllene

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Caryophyllene
IUPAC name

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

Identifiers
CAS number 87-44-5 YesY
PubChem 5281515
ChemSpider 4444848 YesY
UNII BHW853AU9H YesY
ChEBI CHEBI:10357 YesY
ChEMBL CHEMBL445740 YesY
Jmol-3D images {{#if:C1(=C)\CC/C=C(/CC[C@@H]2[C@@H]1CC2(C)C)C|Image 1
Properties
Molecular formula C15H24
Molar mass 204.36 g/mol
Density 0.9052 g/cm3
Boiling point 262-264 °F; 129-130 °C (14 mm Hg)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Caryophyllene /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. In a study conducted by Jürg Gertsch et al. from the Swiss Federal Institute of Technology (ETH Zurich), beta-caryophyllene was shown to be selective agonist of 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]

Caryophyllene oxide is the component responsible for cannabis identification by drug-sniffing dogs[6][7]

Natural sources

The approximate quantity of caryophyllene in the essential oil of each source is given in square brackets ([ ]):

  • Black Caraway (Carum nigrum) [7.8%][9]
  • True cinnamon (Cinnamomum zeylanicum) [6.9–11.1%][22]

Compendial status

Notes and references

  1. ↑ 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. ↑ 2.0 2.1 2.2 Gertsch J, Leonti M, Raduner S, et al. (July 2008). "Beta-caryophyllene is a dietary cannabinoid". Proceedings of the National Academy of Sciences of the United States of America 105 (26): 9099–104. doi:10.1073/pnas.0803601105. PMC 2449371. PMID 18574142. 
  3. ↑ 3.0 3.1 Ormeño E, Baldy V, Ballini C, Fernandez C (September 2008). "Production and diversity of volatile terpenes from plants on calcareous and siliceous soils: effect of soil nutrients". J. Chem. Ecol. 34 (9): 1219–29. doi:10.1007/s10886-008-9515-2. PMID 18670820. 
  4. ↑ Glenn Tinseth, "Hop Aroma and Flavor", January/February 1993, Brewing Techniques. <http://realbeer.com/hops/aroma.html> Accessed July 21, 2010.
  5. ↑ 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. 
  6. ↑ Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects Ethan B Russo. Br J Pharmacol. 2011 August; 163(7): 1344–1364.
  7. ↑ Stahl E, Kunde R. Die Leitsubstanzen der Haschisch-Suchhunde. Kriminalistik: Z Gesamte Kriminal Wiss Prax. 1973;27:385–389.
  8. ↑ Mediavilla, Vito; Simon Steinemann. "Essential oil of Cannabis sativa L. strains". International Hemp Association. Retrieved 11 July 2008. 
  9. ↑ Singh G, Marimuthu P, de Heluani CS, Catalan CA (January 2006). "Antioxidant and biocidal activities of Carum nigrum (seed) essential oil, oleoresin, and their selected components". J. Agric. Food Chem. 54 (1): 174–81. doi:10.1021/jf0518610. PMID 16390196. 
  10. ↑ Alma, M. Hakkı; Ertaş, Murat; Nitz, Siegfrie; Kollmannsberger, Hubert (May 2007). "Chemical composition and content of essential oil from the bud of cultivated Turkish clove" (PDF). In Lucia, Lucian A.; Hubbe, Martin A. BioResources (Raleigh, North Carolina, USA: North Carolina State University) 2 (2): 265–269. ISSN 1930-2126. Retrieved September 6, 2010. "The results showed that the essential oils mainly contained about [...] 3.56% β-Caryophyllene" 
  11. ↑ Clove Essential Oil
  12. ↑ Wang G, Tian L, Aziz N, et al. (November 2008). "Terpene Biosynthesis in Glandular Trichomes of Hop". Plant Physiol. 148 (3): 1254–66. doi:10.1104/pp.108.125187. PMC 2577278. PMID 18775972. 
  13. ↑ Bernotienë, Genovaitë; Nivinskienë, Ona; Butkienë, Rita; Mockutë, Danutë (2004). "Chemical composition of essential oils of hops (Humulus lupulus L.) growing wild in Aukštaitija". Chemija. 2 (Vilnius, Lithuania: Lithuanian Academy of Sciences) 4: 31–36. ISSN 0235-7216. Retrieved September 6, 2010. 
  14. ↑ Zheljazkov VD, Cantrell CL, Tekwani B, Khan SI (January 2008). "Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting". J. Agric. Food Chem. 56 (2): 380–5. doi:10.1021/jf0725629. PMID 18095647. 
  15. ↑ Silva, Maria Goretti de Vasconcelos; Matos, Francisco José de Abreu; Lopes, Paulo Roberto Oliveira; Silva, Fábio Oliveira; Holanda, Márcio Tavares (August 2, 2004). "Composition of essential oils from three Ocimum species obtained by steam and microwave distillation and supercritical CO2 extraction" (PDF). In Cragg, Gordon M.; Bolzani, Vanderlan S.; Rao, G. S. R. Subba. Arkivoc (ARKAT USA, Inc.) 2004 (vi): 66–71. ISSN 1424-6376. Retrieved September 6, 2010. 
  16. ↑ Harvala C, Menounos P, Argyriadou N (February 1987). "Essential Oil from Origanum dictamnus". Planta Med. 53 (1): 107–9. doi:10.1055/s-2006-962640. PMID 17268981. 
  17. ↑ Calvo-Irabien, L. M.; Yam-Puc, J. A.; Dzib, G.; Escalante-Erosa, F.; Peña-Rodriguez, L. M. (July 2009). "Effect of Postharvest Drying on the Composition of Mexican Oregano (Lippia graveolens) Essential Oil". Journal of Herbs, Spices & Medicinal Plants (London, UK: Taylor & Francis) 15 (3): 281–287. doi:10.1080/10496470903379001. ISSN 1540-3580. 
  18. ↑ The essential oil of Origanum vulgare L. ssp. vulgare growing wild in vilnius district (Lithuania) Phytochemistry. 2001 May;57(1):65-9.
  19. ↑ 19.0 19.1 Jirovetz L, Buchbauer G, Ngassoum MB, Geissler M (November 2002). "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 976 (1–2): 265–75. doi:10.1016/S0021-9673(02)00376-X. PMID 12462618. 
  20. ↑ A. Prashar, I. C. Locke, C. S. Evans (2004). Cytotoxicity of lavender oil and its major components to human skin cells. Cell Proliferation 37 (3), 221–229.
  21. ↑ Jamshidi, R.; Afzali, Z.; Afzali, D. (February 2009). "Chemical Composition of Hydrodistillation Essential Oil of Rosemary in Different Origins in Iran and Comparison with Other Countries" (PDF). American-Eurasian Journal of Agricultural & Environmental Sciences (Pakistan: IDOSI Publications) 5 (1): 78–81. ISSN 1990-4053. Retrieved September 6, 2010. 
  22. ↑ 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. 
  23. ↑ 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. 
  24. ↑ Ylang Ylang Essential Oil
  25. ↑ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". Retrieved 29 June 2009. 
  26. ↑ Therapeutic Goods Administration. "Chemical substances". Retrieved 29 June 2009. 

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