Description
β-Caryophyllene is a sesquiterpene that has been found in plants, including
C. sativa, C. indica, and hemp, and has diverse biological activities, including lipid metabolic, antioxidant, anti-neuroinflammatory, anti-proliferative, and antinociceptive properties.
Chemical Properties
β-Caryophyllene has a woody-spicy, dry, clove-like aroma.
Occurrence
Three isomers (α-, β-, and γ-caryophyllene) are found in nature. The β-isomer is the most frequently encountered
and most abundant. This sesquiterpene hydrocarbon occurs naturally in approximately 60 essential oils, mainly in that of
cloves, from which it was originally isolated. The chemical structure has been thoroughly studied; other studies have been conducted
on the isolation and the dipolar moment, as well as on its oxide. Reported found in lime peel oil, lemon, grapefruit, guava fruit, raspberry,
black currant, carrot, celery seed, cinnamon bark, anise, nutmeg, cumin seed, ginger, pepper, peppermint oil, mace, laurel and
caraway herb.
Uses
β-Caryophyllene is notable for having a cyclobutane ring, a rarity in nature. β-Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. β-Caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.
Preparation
Isolated from oil of clove stems and separated from eugenol by treating the oil with 7% sodium carbonate solution,
extracting with ether, repeating the carbonate treatment on the concentrated extracts, and finally steam distilling.
Definition
ChEBI: A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of <greek beta-caryophyllene, occurring in many essential oils, particularly oil of cloves.
Aroma threshold values
Detection at 64 to 90 ppb
Taste threshold values
Taste characteristics at 50 ppm: spicy, pepper-like, woody, camphoraceous with a citrus background.
Synthesis Reference(s)
Journal of the American Chemical Society, 86, p. 485, 1964
DOI: 10.1021/ja01057a040
Air & Water Reactions
Insoluble in water.
Reactivity Profile
The unsaturated aliphatic hydrocarbons, such as BETA-CARYOPHYLLENE, are generally much more reactive than the alkanes. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, compounds in this class can undergo very exothermic addition polymerization reactions.
Health effects
β-caryophyllene has shown anti-inflammatory activity via decreasing TLR-4, IL-1, and TNF-α levels. It attenuated oxidative stress by restoring antioxidant enzymes and repressing lipid peroxidation as well as GSH depletion.
Fire Hazard
BETA-CARYOPHYLLENE is combustible.
Safety Profile
A skin irritant.
Combustible liquid. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Carcinogenicity
Caryophyllene showed significant
activity as an inducer of the detoxifying enzyme glutathione
S-transferase in the mouse liver and small intestine.
The ability of natural anticarcinogens to induce detoxifying
enzymes has been found to correlate with their activity in the
inhibition of chemical carcinogenesis (253a).
References
[1] HAZEKAMP A, TEJKALOVá K, PAPADIMITRIOU S A. Cannabis: From Cultivar to Chemovar II—A Metabolomics Approach to Cannabis Classification[C]. 2016: 0. DOI:
10.1089/can.2016.0017[2] CHUNYAN WU . trans-Caryophyllene is a natural agonistic ligand for peroxisome proliferator-activated receptor-α[J]. Bioorganic & Medicinal Chemistry Letters, 2014, 24 14: Pages 3168-3174. DOI:
10.1016/j.bmcl.2014.04.112[3] GUIFANG WANG Jingwei D Weibin Ma. β-Caryophyllene (BCP) ameliorates MPP+ induced cytotoxicity.[J]. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 2018: 1086-1091. DOI:
10.1016/j.biopha.2018.03.168[4] YUJIE CHENG Sha L Zhi Dong. β-Caryophyllene ameliorates the Alzheimer-like phenotype in APP/PS1 Mice through CB2 receptor activation and the PPARγ pathway.[J]. Pharmacology, 2014, 94 1-2: 1-12. DOI:
10.1159/000362689[5] AMINE BAHI . β-Caryophyllene, a CB2 receptor agonist produces multiple behavioral changes relevant to anxiety and depression in mice[J]. Physiology & Behavior, 2014, 135: Pages 119-124. DOI:
10.1016/j.physbeh.2014.06.003[6] L.I.G. PAULA-FREIRE . The oral administration of trans-caryophyllene attenuates acute and chronic pain in mice[J]. Phytomedicine, 2014, 21 3: Pages 356-362. DOI:
10.1016/j.phymed.2013.08.006[7] JüRG GERTSCH. Beta-caryophyllene is a dietary cannabinoid.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2008, 105 26: 9099-9104. DOI:
10.1073/pnas.0803601105[8] HANNAH C. HUFF. Differential Interactions of Selected Phytocannabinoids with Human CYP2D6 Polymorphisms[J]. Biochemistry Biochemistry, 2021, 60 37: 2749-2760. DOI:
10.1021/acs.biochem.1c00158
