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Caryophyllene

Caryophyllene
Names
Preferred IUPAC name
(1R,4E,9S)-4,11,11-Trimethyl-8-methylidenebicyclo[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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.588 Edit this at Wikidata
EC Number
  • 201-746-1
KEGG
UNII
  • 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-/m1/s1 checkY
    Key: NPNUFJAVOOONJE-GFUGXAQUSA-N checkY
  • InChI=1/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-/m1/s1
    Key: NPNUFJAVOOONJE-GFUGXAQUBC
  • C1(=C)\CC/C=C(/CC[C@@H]2[C@@H]1CC2(C)C)C
Properties
C15H24
Molar mass 204.357 g·mol−1
Density 0.9052 g/cm3 (17 °C)[1]
Boiling point 262–264 °C (504–507 °F; 535–537 K)[2]
Hazards
GHS labelling:[1]
GHS07: Exclamation markGHS08: Health hazard
Warning
H304, H317
P261, P272, P280, P301+P316, P302+P352, P321, P331, P333+P317, P362+P364, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Caryophyllene (/ˌkærioʊˈfɪliːn/), more formally (−)-β-caryophyllene (BCP), is a natural bicyclic sesquiterpene that occurs widely in nature. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature. [3]

Production

Caryophyllene can be produced synthetically,[4] but it is invariably obtained from natural sources because it is widespread. It 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, copaiba, rosemary, and hops.[3] 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 one of the chemical compounds that contributes to the aroma of black pepper.[5]

Basic research

β-Caryophyllene is under basic research for its potential action as an agonist of the cannabinoid receptor type 2 (CB2 receptor).[6] In other basic studies, β-caryophyllene has a binding affinity of Ki = 155 nM at the CB2 receptors.[7]

β-Caryophyllene has the highest cannabinoid activity compared to the ring opened isomer α-caryophyllene humulene which may modulate CB2 activity.[8] To compare binding, cannabinol binds to the CB2 receptors as a partial agonist with an affinity of Ki = 126.4 nM,[9] while delta-9-tetrahydrocannabinol binds to the CB2 receptors as a partial agonist with an affinity of Ki = 36 nM.[10]

Safety

Caryophyllene has been given generally recognized as safe (GRAS) designation by the FDA and is approved by the FDA for use as a food additive, typically for flavoring.[11][12] Rats given up to 700 mg/kg daily for 90 days did not produce any significant toxic effects.[13] Caryophyllene has an LD50 of 5,000 mg/kg in mice.[14][15]

Metabolism and derivatives

14-Hydroxycaryophyllene oxide (C15H24O2) was isolated from the urine of rabbits treated with (−)-caryophyllene (C15H24). The X-ray crystal structure of 14-hydroxycaryophyllene (as its acetate derivative) has been reported.[16]

The metabolism of caryophyllene progresses through (−)-caryophyllene oxide (C15H24O) since the latter compound also afforded 14-hydroxycaryophyllene (C15H24O) as a metabolite.[17]

Caryophyllene (C15H24) → caryophyllene oxide (C15H24O) → 14-hydroxycaryophyllene (C15H24O) → 14-hydroxycaryophyllene oxide (C15H24O2).

Caryophyllene oxide,[18] in which the alkene group of caryophyllene has become an epoxide, is the component responsible for cannabis identification by drug-sniffing dogs[19][20] and is also an approved food additive, often as flavoring.[12] Caryophyllene oxide may have negligible cannabinoid activity.[21]

Natural sources

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

Biosynthesis

Caryophyllene is a common sesquiterpene among plant species. It is biosynthesized from the common terpene precursors dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). First, single units of DMAPP and IPP are reacted via an SN1-type reaction with the loss of pyrophosphate, catalyzed by the enzyme GPPS2, to form geranyl pyrophosphate (GPP). This further reacts with a second unit of IPP, also via an SN1-type reaction catalyzed by the enzyme IspA, to form farnesyl pyrophosphate (FPP). Finally, FPP undergoes QHS1 enzyme-catalyzed intramolecular cyclization to form caryophyllene.[39]

Biosynthesis of caryophyllene

Compendial status

Further reading

  • Ghelardini, C.; Galeotti, N.; Di Cesare Mannelli, L.; Mazzanti, G.; Bartolini, A. (2001). "Local anaesthetic activity of beta-caryophyllene". Farmaco. 56 (5–7): 387–389. doi:10.1016/S0014-827X(01)01092-8. hdl:2158/397975. PMID 11482764.

Notes and references

  1. ^ SciFinder Record, CAS Registry Number 87-44-5
  2. ^ Baker, R. R. (2004). "The pyrolysis of tobacco ingredients". Journal of Analytical and Applied Pyrolysis. 71 (1): 223–311. Bibcode:2004JAAP...71..223B. doi:10.1016/s0165-2370(03)00090-1.
  3. ^ a b Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  4. ^ Corey, E. J.; Mitra, R. B.; Uda, H. (1964). "Total Synthesis of d,l-Caryophyllene and d,l-Isocaryophyllene". Journal of the American Chemical Society. 86 (3): 485–492. Bibcode:1964JAChS..86..485C. doi:10.1021/ja01057a040.
  5. ^ a b Jirovetz, L.; Buchbauer, G.; Ngassoum, M. B.; 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". Journal of Chromatography A. 976 (1–2): 265–275. doi:10.1016/S0021-9673(02)00376-X. PMID 12462618.
  6. ^ Ceccarelli, Ilaria; Fiorenzani, Paolo; Pessina, Federica; Pinassi, Jessica; Aglianò, Margherita; Miragliotta, Vincenzo; Aloisi, Anna Maria (18 August 2020). "The CB2 Agonist β-Caryophyllene in Male and Female Rats Exposed to a Model of Persistent Inflammatory Pain". Frontiers in Neuroscience. 14: 850. doi:10.3389/fnins.2020.00850. PMC 7461959. PMID 33013287.
  7. ^ Alberti, Thaís Barbosa; Barbosa, Wagner Luiz Ramos; Vieira, José Luiz Fernandes; Raposo, Nádia Rezende Barbosa; Dutra, Rafael Cypriano (1 April 2017). "(−)-β-Caryophyllene, a CB2 Receptor-Selective Phytocannabinoid, Suppresses Motor Paralysis and Neuroinflammation in a Murine Model of Multiple Sclerosis". International Journal of Molecular Sciences. 18 (4): 691. doi:10.3390/ijms18040691. PMC 5412277. PMID 28368293.
  8. ^ Hashiesh, Hebaallah Mamdouh; Sharma, Charu; Goyal, Sameer N.; Sadek, Bassem; Jha, Niraj Kumar; Kaabi, Juma Al; Ojha, Shreesh (1 August 2021). "A focused review on CB2 receptor-selective pharmacological properties and therapeutic potential of β-caryophyllene, a dietary cannabinoid". Biomedicine & Pharmacotherapy. 140: 111639. doi:10.1016/j.biopha.2021.111639. PMID 34091179. S2CID 235362290.
  9. ^ Russo, Ethan B.; Marcu, Jahan (2017). "Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads". Cannabinoid Pharmacology. Advances in Pharmacology. Vol. 80. pp. 67–134. doi:10.1016/bs.apha.2017.03.004. ISBN 978-0-12-811232-8. PMID 28826544.
  10. ^ Bow, Eric W.; Rimoldi, John M. (28 June 2016). "The Structure–Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry. 8: 17–39. doi:10.4137/PMC.S32171. PMC 4927043. PMID 27398024.
  11. ^ "Nomination Background: beta-Caryophyllene (CASRN: 87-44-5)" (PDF).
  12. ^ a b "CFR - Code of Federal Regulations Title 21".
  13. ^ Schmitt, D.; Levy, R.; Carroll, B. (2016). "Toxicological Evaluation of β-Caryophyllene Oil". International Journal of Toxicology. 35 (5): 558–567. doi:10.1177/1091581816655303. PMID 27358239. S2CID 206689471.
  14. ^ "β-Caryophyllene - SDS". Retrieved 18 April 2024.
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  16. ^
  17. ^ "Caryophyllene oxide – C15H24O". PubChem. Retrieved September 8, 2016.
  18. ^ Yang, Depo; Michel, Laura; Chaumont, Jean-Pierre; Millet-Clerc, Joëlle (1999). "Use of caryophyllene oxide as an antifungal agent in an in vitro experimental model of onychomycosis". Mycopathologia. 148 (2): 79–82. doi:10.1023/a:1007178924408. PMID 11189747. S2CID 24242933.
  19. ^ Russo, Ethan B (August 2011). "Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects: Phytocannabinoid-terpenoid entourage effects". British Journal of Pharmacology. 163 (7): 1344–1364. doi:10.1111/j.1476-5381.2011.01238.x. PMC 3165946. PMID 21749363.
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  25. ^ Wang, Guodong; Tian, Li; Aziz, Naveed; Broun, Pierre; Dai, Xinbin; He, Ji; King, Andrew; Zhao, Patrick X.; Dixon, Richard A. (6 November 2008). "Terpene Biosynthesis in Glandular Trichomes of Hop". Plant Physiology. 148 (3): 1254–1266. doi:10.1104/pp.108.125187. PMC 2577278. PMID 18775972.
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  27. ^ Zheljazkov, V. D.; Cantrell, C. L.; Tekwani, B.; Khan, S. I. (January 2008). "Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting". Journal of Agricultural and Food Chemistry. 56 (2): 380–5. Bibcode:2008JAFC...56..380Z. doi:10.1021/jf0725629. PMID 18095647.
  28. ^ Vasconcelos Silva, M. G.; Abreu Matos, F. J.; Oliveira Lopes, P. R.; Oliveira Silva, F.; Tavares Holanda, M. (August 2, 2004). Cragg, G. M.; Bolzani, V. S.; Rao, G. S. R. S. (eds.). "Composition of essential oils from three Ocimum species obtained by steam and microwave distillation and supercritical CO2 extraction". Arkivoc. 2004 (6): 66–71. doi:10.3998/ark.5550190.0005.609. hdl:2027/spo.5550190.0005.609.
  29. ^ Harvala C, Menounos P, Argyriadou N (February 1987). "Essential oil from Origanum dictamnus". Planta Medica. 53 (1): 107–109. doi:10.1055/s-2006-962640. PMID 17268981. S2CID 260278580.
  30. ^ Calvo Irabién, L. M.; Yam-Puc, J. A.; Dzib, G.; Escalante Erosa, F.; Peña Rodríguez, L. M. (July 2009). "Effect of postharvest drying on the composition of Mexican oregano (Lippia graveolens) essential oil". Journal of Herbs, Spices & Medicinal Plants. 15 (3): 281–287. doi:10.1080/10496470903379001. S2CID 86208062.
  31. ^ Mockutė, D.; Bernotienė, G.; Judžentienė, A. (May 2001). "The essential oil of Origanum vulgare L. ssp. vulgare growing wild in Vilnius district (Lithuania)". Phytochemistry. 57 (1): 65–69. Bibcode:2001PChem..57...65M. doi:10.1016/s0031-9422(00)00474-x. PMID 11336262.
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  33. ^ Umezu, T.; Nagano, K.; Ito, H.; Kosakai, K.; Sakaniwa, M.; Morita, M. (December 2006). "Anticonflict effects of lavender oil and identification of its active constituents". Pharmacology Biochemistry and Behavior. 85 (4): 713–721. doi:10.1016/j.pbb.2006.10.026. PMID 17173962. S2CID 21779233.
  34. ^ Ormeño, E.; Baldy, V.; Ballini, C.; Fernández, C. (September 2008). "Production and diversity of volatile terpenes from plants on calcareous and siliceous soils: effect of soil nutrients". Journal of Chemical Ecology. 34 (9): 1219–1229. Bibcode:2008JCEco..34.1219O. doi:10.1007/s10886-008-9515-2. PMID 18670820. S2CID 28717342.
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  36. ^ Ahmed, Aftab; Choudhary, M. Iqbal; Farooq, Afgan; Demirci, Betül; Demirci, Fatih; Başer, K. Hüsnü Can (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.
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  39. ^ Yang, Jianming; Li, Zhengfeng; Guo, Lizhong; Du, Juan; Bae, Hyeun-Jong (December 2016). "Biosynthesis of β-caryophyllene, a novel terpene-based high-density biofuel precursor, using engineered Escherichia coli". Renewable Energy. 99: 216–223. Bibcode:2016REne...99..216Y. doi:10.1016/j.renene.2016.06.061.
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