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Caryophyllene

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Title: Caryophyllene  
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Subject: Cannabis flower essential oil, CP 55,940, SR-144,528, N-Arachidonoyl dopamine, JWH-133
Collection: Alkenes, Cannabinoids, Cb2 Receptor Agonists, Flavors, Hydrocarbons, Sesquiterpenes
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Caryophyllene

Caryophyllene
Names
IUPAC names
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
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
PubChem
UNII  Y
Properties
C15H24
Molar mass 204.36 g·mol−1
Density 0.9052 g/cm3 (17 °C)[1]
Boiling point 254–257 °C (489–495 °F; 527–530 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Caryophyllene , 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),[3] the essential oil of hemp Cannabis sativa,[4] rosemary Rosmarinus oficinalis,[5] and hops.[6] 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. Beta-caryophyllene was shown to be selective agonist of cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.[4] Antinociceptive,[7] neuroprotective,[8] anxiolytic and antidepressant [9] and anti-alcoholism [10] activity have been uncovered. Because 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 psychotomimetic effects.

The first total synthesis of caryophyllene in 1964 by

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  4. ^ a b c 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.  
  5. ^ a b 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.  
  6. ^ Glenn Tinseth, "Hop Aroma and Flavor", January/February 1993, Brewing Techniques. Accessed July 21, 2010.
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  8. ^ Guimarães-Santos, Adriano (2012). "Copaiba Oil-Resin Treatment Is Neuroprotective and Reduces Neutrophil Recruitment and Microglia Activation after Motor Cortex Excitotoxic Injury". Evidence-Based Complementary and Alternative Medicine 2012: 1–9.  
  9. ^ Bahi Amine, Al Mansouri Shamma, Al Memari Elyazia, Al Ameri Mouza, Nurulain Syed M., Ojha Shreesh. (2014). "β-Caryophyllene, a CB2 receptor agonist produces multiple behavioral changes relevant to anxiety and depression in mice.". Physiology & behavior 135: 119–124.  
  10. ^ Al Mansouri Shamma, Ojha Shreesh, Al Maamari Elyazia, Al Ameri Mouza, Nurulain Syed M., Bahi Amine. (2014). "The cannabinoid receptor 2 agonist, β-caryophyllene, reduced voluntary alcohol intake and attenuated ethanol-induced place preference and sensitivity in mice.". Pharmacology, biochemistry, and behavior. 2014;124C:260-268 124: 260–268.  
  11. ^ 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.  
  12. ^ Ethan (2011). "Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects". Br J Pharmacol 163 (7): 1344–1364.  
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  18. ^ Clove Essential Oil
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  22. ^ 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. extraction"2 species obtained by steam and microwave distillation and supercritical COOcimum"Composition of essential oils from three (PDF). Arkivoc (ARKAT USA, Inc.) 2004 (vi): 66–71.  
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  25. ^ The essential oil of Origanum vulgare L. ssp. vulgare growing wild in vilnius district (Lithuania) Phytochemistry. 2001 May;57(1):65-9.
  26. ^ a b 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.  
  27. ^ 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.
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  29. ^ 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.  
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  31. ^ Ylang Ylang Essential Oil
  32. ^ "Chemistry and biological activities of terpenoids from copaiba (Copaifera spp.) oleoresins.". Molecules 17 (4): 3866–89. 2012.  
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  36. ^ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". Retrieved 29 June 2009. 
  37. ^  

Notes and references

  • Food Chemical Codex[36][37]

Compendial status

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

Natural sources

Caryophyllene oxide, in which the olefin of caryophyllene has become an epoxide, is the component responsible for cannabis identification by drug-sniffing dogs[12][13] and is also an approved food flavoring.[14]

[11]

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