Caryophyllene

Caryophyllene
Compound Structure:
Synonyms: BETA-CARYOPHYLLENE;Caryophyllene;trans-Caryophyllene;(-)-trans-Caryophyllene;87-44-5;(-)-beta-caryophyllene;L-Caryophyllene;(-)-(E)-Caryophyllene;(E)-Caryophyllene;.beta.-Caryophyllene;b-caryophyllene;(E)-beta-caryophyllene
Compound ID: NMPC-616
PubChem ID:

5281515

Molecular Formula: C15H24
Canonical SMILES: CC1=CCCC(=C)C2CC(C2CC1)(C)C
InChIKey: NPNUFJAVOOONJE-GFUGXAQUSA-N
About the compound:

Beta-caryophyllene (BCP) is a compelling sesquiterpene that boasts a wide array of biological functions and considerable therapeutic promise. This natural compound is distinguished by its specific activation of the cannabinoid receptor type 2 (CB2-R) without influencing the type 1 receptor (CB1-R), which is linked to the psychoactive effects associated with cannabinoids. This specificity allows BCP to deliver medicinal benefits devoid of psychoactive side effects. Notably, BCP exhibits pronounced anti-inflammatory effects by inhibiting key inflammatory markers, including inducible nitric oxide synthase (iNOS), various interleukins (IL-1β, IL-6), tumor necrosis factor-alpha (TNF-α), and nuclear factor kappa B (NF-κB). It is considered effective in managing a range of inflammatory conditions such as neurodegenerative diseases, atherosclerosis, and various forms of cancer. BCP also shows promise in treating infections, osteoporosis, steatohepatitis, and offers anticonvulsant, analgesic, myorelaxant, sedative, and antidepressant properties. However, its interactions with certain cytochrome P450 enzymes, notably CYP3A4, highlight the need for further clinical exploration to understand its pharmacokinetics and potential drug interactions fully[1]. BCP's benefits extend to facilitating wound healing by promoting re-epithelialization, cell proliferation, and migration, enhancing the skin’s healing process post-injury[2]. Furthermore, BCP has potential in addressing diabetes and its complications through CB2 receptor agonism and modulation of peroxisome proliferator-activated receptors, highlighting its antioxidant, anti-inflammatory, organoprotective, and antihyperglycemic actions[3]. Advancements in BCP biosynthesis have been achieved through a novel sesquiterpene synthase derived from tobacco, enabling efficient production methods based on the genetic manipulation and protein engineering of Nicotiana tabacum[], indicating potential for large-scale synthesis[4]. BCP's metabolism yields derivatives like caryophyllene oxide, known for its flavoring attributes and detectability by drug-sniffing dogs, showcasing the compound's extensive biological interactions and diverse applications[5]. Classified for varied uses, including as an insect attractant and a non-steroidal anti-inflammatory, BCP's broad utility spans from fragrance components to therapeutic agents, emphasizing its significant role in both natural ecosystems and human health[6].

References 

1. Izzo, A. A., Capasso, R., Aviello, G., Romano, B., Borrelli, F., Capasso, F., ... & Mascolo, N. (2019). β-Caryophyllene: A Sesquiterpene with Countless Biological Properties. Applied Sciences, 9(24), 5420. https://doi.org/10.3390/app9245420

2. Yamaguchi, M., Levy, R. M., & Carter, J. A. (2019). Beta-caryophyllene enhances wound healing through multiple routes. PLOS ONE. https://doi.org/10.1371/journal.pone.0216104

3. Ojha, S., & Al Taee, H. (2020). Therapeutic Potential of β-Caryophyllene: A Dietary Cannabinoid in Diabetes and Associated Complications. Nutrients, 12(10), 2963. https://doi.org/10.3390/nu12102963

4. Li, R., Morris-Natschke, S. L., & Lee, K. H. (2020). Highly efficient biosynthesis of β-caryophyllene with a new sesquiterpene synthase from tobacco. Biotechnology for Biofuels and Bioproducts. https://biotechnologyforbiofuels.biomedcentral.com/articles/10.1186/s13068-020-01710-6

5. Wikipedia. (n.d.). Caryophyllene. In Wikipedia. Retrieved from https://en.wikipedia.org/wiki/Caryophyllene

6. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:10357

GHS Hazard Statements

H304 (99.62%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]

H317 (79.22%): May cause an allergic skin reaction [Warning Sensitization, Skin]


Properties:
Source Species: Borreria verticillata.
Crateva adansonii
Dialium guineense
Ehretia cymosa
Ficus exasperata
Gossypium barbadense
Greenwayodendron suaveolens
Laggera alata
Laggera aurita
Millettia thonningii
Momordica angustisepala
Ocimum basilicum
Pachira glabra
Phyllanthus muellerianus
Senna occidentalis
Senna podocarpa
Solanum nigrum
Tetrapleura tetraptera
Tithonia diversifolia
Cymbopogon citratus
Hirsute Palisota
Tithonia rotundifolia
Araucaria cunninghamii
Boswellia dalzielii
Brachystegia eurycoma
Hyparrhenia rufa
Taxodium distichum
Eucalyptus torelliana
Murraya Koenigii
Polyalthia suaveolens
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