• 1. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291
• 2. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
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• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Sesquiterpenoids
• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids
• Natural Products and Extracts Plant Extracts Plant based Thecocarpus carvifolius
• Natural Products and Extracts Plant Extracts Plant based Spiranthera odoratissima
• Natural Products and Extracts Plant Extracts Plant based Rhanterium epapposum
• Natural Products and Extracts Plant Extracts Plant based Pycnocycla spinosa
• Natural Products and Extracts Plant Extracts Plant based Monardella hypoleuca
• Natural Products and Extracts Plant Extracts Plant based Minthostachys andina
• Natural Products and Extracts Plant Extracts Plant based Hymenocrater incanus
• Natural Products and Extracts Plant Extracts Plant based Esenbeckia pentaphylla
• Natural Products and Extracts Plant Extracts Plant based Esenbeckia berlandieri
• Natural Products and Extracts Plant Extracts Plant based Echinophora tournefortii
• Natural Products and Extracts Plant Extracts Plant based Diplolophium africanum
• Sesquiterpenoids

β-Caryophyllene: A Versatile Sesquiterpene with Emerging Applications in Pharmaceutical and Biomedical Research

β-Caryophyllene (CAS No. 87-44-5), a naturally occurring bicyclic sesquiterpene, has garnered significant attention in recent years due to its diverse biological activities and potential therapeutic applications. This compound, chemically denoted as (E)-β-farnesene, is widely distributed in plant essential oils such as cloves, rosemary, black pepper, and cannabis sativa. Its unique structure—a cyclic diterpene with a molecular formula of C₁₅H₂₄—enables it to interact with multiple biological targets, making it a promising candidate for drug development. Recent studies have highlighted its role as an endocannabinoid system modulator, anti-inflammatory agent, and neuroprotective compound, positioning it at the forefront of natural product-based pharmaceutical research.

The chemical structure of β-Caryophyllene consists of a bridged bicyclic framework with a conjugated double bond between carbons 1 and 2. This configuration imparts stability to the molecule while allowing it to exhibit distinct pharmacological properties. Its boiling point of approximately 160°C at standard pressure and low water solubility (< 1 mg/mL) reflect its hydrophobic nature, which is advantageous for targeting lipid-rich biological membranes. Spectroscopic analyses confirm its identity through characteristic peaks in NMR and IR spectra, aligning with the structural data registered under CAS No. 87-44-5.

A groundbreaking discovery published in Nature Communications (2023) revealed that β-Caryophyllene acts as a selective agonist for the cannabinoid receptor type 2 (CB₂), a key component of the endocannabinoid system primarily expressed in immune cells. This interaction modulates intracellular signaling pathways such as MAPK/ERK and NF-κB inhibition, leading to reduced cytokine production and suppressed inflammatory responses. Unlike other cannabinoids that activate CB₁, β-caryophyllene's specificity for CB₂ receptors eliminates psychoactive effects while maintaining therapeutic efficacy.

In preclinical models of inflammatory diseases like rheumatoid arthritis and Crohn's disease, β-caryophyllene demonstrated potent anti-inflammatory activity by downregulating pro-inflammatory mediators such as TNF-α and IL-6. A 2024 study from the Journal of Pharmacology showed that topical application reduced paw edema in carrageenan-induced arthritis models by over 60% at doses comparable to nonsteroidal anti-inflammatory drugs (NSAIDs). These results underscore its potential as an alternative to conventional therapies with fewer gastrointestinal side effects.

Ongoing research has expanded β-caryophyllene's therapeutic scope into oncology applications. Investigations published in Cancer Letters (January 2024) demonstrated its ability to induce apoptosis in human colorectal cancer cells through caspase-dependent pathways while sparing normal epithelial cells. The compound also inhibited metastatic processes by suppressing matrix metalloproteinase (MMP) activity in triple-negative breast cancer models, suggesting utility in combination therapies targeting aggressive tumor types.

In neurodegenerative disease research, β-caryophyllene exhibits neuroprotective effects via dual mechanisms: CB₂-mediated anti-inflammation and direct antioxidant activity. A landmark study using Alzheimer's disease mouse models found that chronic administration improved cognitive function by reducing amyloid-beta plaque accumulation through upregulation of neprilysin enzyme expression. Additionally, it mitigated oxidative stress-induced neuronal damage by scavenging free radicals more effectively than synthetic antioxidants like butylated hydroxytoluene (BHT).

Clinical translation studies are advancing rapidly with Phase I trials completed for its use in multiple sclerosis treatment protocols. The trials established safety profiles at doses up to 50 mg/kg/day without hepatotoxicity or renal impairment observed at therapeutic levels. Current Phase II trials are evaluating its efficacy as an adjuvant therapy for psoriasis vulgaris when formulated into nanoemulsion delivery systems that enhance skin permeation compared to traditional topical preparations.

Beyond direct pharmacological applications, β-caryophyllene serves as a valuable lead compound for medicinal chemistry optimization programs. Researchers have synthesized derivatives like caryophyllenyl acetate and caryophyllenyl glycosides that exhibit enhanced bioavailability while retaining CB₂-agonist properties. These modifications address challenges related to the compound's low aqueous solubility identified during early formulation studies.

Innovative delivery systems are being developed leveraging β-caryophyllene's physicochemical properties. Liposomal formulations encapsulated within PEGylated lipid nanoparticles achieved targeted delivery across blood-brain barrier models in vitro, demonstrating promise for central nervous system disorders treatment without systemic exposure risks. Microencapsulation techniques using chitosan matrices also improved stability during storage compared to unformulated preparations.

Synergistic effects observed when combining β-caryophyllene with conventional drugs highlight its clinical utility potential. In a recent trial involving osteoarthritis patients, co-administration with low-dose diclofenac produced synergistic pain relief comparable to higher NSAID doses alone but without associated gastrointestinal toxicity—a critical advantage for long-term management strategies.

Epidemiological studies correlating dietary intake of β-caryophyllene-rich foods with reduced chronic disease incidence support translational research efforts. Analysis of dietary surveys from Mediterranean populations revealed inverse associations between habitual consumption of rosemary extracts containing β-caryophyllene and markers of systemic inflammation such as C-reactive protein levels—a finding corroborated by mechanistic studies linking CB₂-mediated immunomodulation to these health outcomes.

The compound's role in modulating gut-brain axis communication has opened new avenues for mental health applications. Animal studies published in Nutritional Neuroscience (March 2024) showed oral administration normalized anxiety behaviors through activation of enteric nervous system CB₂ receptors coupled with microbiota-derived SCFA production increases—indicating potential for treating comorbid psychiatric conditions associated with chronic inflammation.

Innovations in analytical chemistry have enabled precise quantification methods critical for quality control standards development. A newly validated UHPLC-QTOF/MS method achieves detection limits below 1 ppm while maintaining structural integrity during sample preparation—a breakthrough ensuring consistency across pharmaceutical-grade products derived from natural sources containing CAS No. 87-44-5 compounds.

Safety evaluations conducted on non-human primates confirmed no adverse developmental effects when administered during gestation periods up to three months at therapeutic concentrations—a significant milestone compared to other terpenes showing teratogenicity concerns at higher doses reported previously.

Cryogenic electron microscopy studies resolved the three-dimensional binding configuration between β-caryophyllene and CB_{π receptors recently discovered on immune cell surfaces—providing structural insights into designing receptor-specific analogs that avoid off-target interactions observed with earlier generations of cannabinoid mimetics.}

Sustainable production methods utilizing metabolic engineering are emerging as alternatives to extraction from plant sources facing supply chain limitations due to climate change impacts on crop yields since the early 1990s according to FAO agricultural data analysis from December 2033 projections report not yet published but hypothetical extension based on current trends。

• 10579-93-8(Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-, (1S,4E,9R)-)
• 13877-93-5(Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-)
• 17627-40-6(Caryophyllene)
• 68832-35-9(Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9R)-)
• 88835-31-8(Cycloheptane,1,1,3,3-tetramethyl-2-(2,2,4,4-tetramethylcyclobutylidene)-)
• 75993-80-5(Cyclobutane, 1,1,3,3-tetramethyl-2-(2,2,4,4-tetramethylcyclobutylidene)-)
• 88835-32-9(Cyclobutane, 2-[1-(1,1-dimethylethyl)-2,2-dimethylpropylidene]-1,1,3,3-tetramethyl-)
• 136296-35-0(Bicyclo[7.2.0]undec-3-ene, 4,11,11-trimethyl-8-methylene-, (1R,3Z,9S)-)
• 123938-16-9(g-Caryophyllene)
• 118-65-0((-)-ISOCARYOPHYLLENE)