87-44-5 Usage
Description
BETA-CARYOPHYLLENE, also known as β-Caryophyllene, is a sesquiterpene compound found in various plants, including C. sativa, C. indica, and hemp. It possesses a cyclobutane ring, which is a rare feature in nature, and contributes to the spiciness of black pepper. BETA-CARYOPHYLLENE exhibits diverse biological activities, such as lipid metabolic, antioxidant, anti-neuroinflammatory, anti-proliferative, and antinociceptive properties. BETA-CARYOPHYLLENE acts as an agonist of the cannabinoid (CB) receptor CB2 and peroxisome proliferator-activated receptor α (PPARα), playing a significant role in various therapeutic applications.
Uses
Used in Anti-inflammatory Applications:
BETA-CARYOPHYLLENE is used as an anti-inflammatory agent for its selective binding to the cannabinoid receptor type-2 (CB2), exerting significant cannabimimetic anti-inflammatory effects in mice.
Used in Neuroprotection:
BETA-CARYOPHYLLENE is used as a neuroprotective agent for its ability to reduce the production of reactive oxygen species (ROS) in and protect against cytotoxicity of SH-SY5Y cells induced by 1-methyl-4-pheylpyridinium (MPP+). It also decreases the β-amyloid burden in the hippocampus and cerebral cortex, improving memory in an APP/PS1 transgenic mouse model of Alzheimer’s disease.
Used in Anxiety and Depression Treatment:
BETA-CARYOPHYLLENE is used as an anxiolytic-like and antidepressant-like agent, as evidenced by its ability to increase the number of entries into and the time spent in the open arms of the elevated plus maze and the time spent immobile in the forced swim test. These effects can be blocked by the CB2 receptor antagonist AM630, indicating the involvement of the CB2 receptor in its anxiolytic and antidepressant activities.
Used in Antioxidant Applications:
BETA-CARYOPHYLLENE is used as an antioxidant agent due to its ability to reduce oxidative stress and protect cells from damage caused by reactive oxygen species.
Used in Lipid Metabolism Regulation:
BETA-CARYOPHYLLENE is used as a regulator of lipid metabolism, as it exhibits agonistic activity on peroxisome proliferator-activated receptor α (PPARα), which plays a crucial role in lipid homeostasis and energy balance.
Used in Anti-proliferative Applications:
BETA-CARYOPHYLLENE is used as an anti-proliferative agent, potentially inhibiting the growth of cancer cells and contributing to cancer treatment strategies.
Used in Pain Management:
BETA-CARYOPHYLLENE is used as an analgesic agent, providing pain relief through its antinociceptive properties.
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.
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.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 87-44-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 87-44:
(4*8)+(3*7)+(2*4)+(1*4)=65
65 % 10 = 5
So 87-44-5 is a valid CAS Registry Number.
InChI:InChI=1/C14H22/c1-10-5-7-11(2)12-9-14(3,4)13(12)8-6-10/h5,12-13H,2,6-9H2,1,3-4H3/b10-5+/t12-,13-/m1/s1
87-44-5Relevant articles and documents
Yano,Nishijima
, p. 1207 (1974)
Four-Step Access to the Sesquiterpene Natural Product Presilphiperfolan-1β-ol and Unnatural Derivatives via Supramolecular Catalysis
Bissegger, Fabian,Levi, Shani,Major, Dan T.,Némethová, Ivana,Prescimone, Alessandro,Schmid, Dario,Syntrivanis, Leonidas-Dimitrios,Tiefenbacher, Konrad
supporting information, p. 5894 - 5900 (2020/04/10)
Terpenes constitute one of the most structurally varied classes of natural products. A wide range of these structures are produced in nature by type I terpene cyclase enzymes from one single substrate. However, such reactivity has proven difficult to reproduce in solution with man-made systems. Herein we report the shortest synthesis of the tricyclic sesquiterpene presilphiperfolan-1β-ol to date, utilizing the supramolecular resorcinarene capsule as catalyst for the key step. This synthetic approach also allows access to unnatural derivatives of the natural product, which would not be accessible through the biosynthetic machinery. Additionally, this study provides useful insight into the biosynthesis of the presilphiperfolanol natural products, including the first experimental evidence consistent with the proposed biosynthetic connection between caryophyllene and the presilphiperfolanols.
An Unusual Skeletal Rearrangement in the Biosynthesis of the Sesquiterpene Trichobrasilenol from Trichoderma
Murai, Keiichi,Lauterbach, Lukas,Teramoto, Kazuya,Quan, Zhiyang,Barra, Lena,Yamamoto, Tsuyoshi,Nonaka, Kenichi,Shiomi, Kazuro,Nishiyama, Makoto,Kuzuyama, Tomohisa,Dickschat, Jeroen S.
supporting information, p. 15046 - 15050 (2019/09/12)
The skeletons of some classes of terpenoids are unusual in that they contain a larger number of Me groups (or their biosynthetic equivalents such as olefinic methylene groups, hydroxymethyl groups, aldehydes, or carboxylic acids and their derivatives) than provided by their oligoprenyl diphosphate precursor. This is sometimes the result of an oxidative ring-opening reaction at a terpene-cyclase-derived molecule containing the regular number of Me group equivalents, as observed for picrotoxan sesquiterpenes. In this study a sesquiterpene cyclase from Trichoderma spp. is described that can convert farnesyl diphosphate (FPP) directly via a remarkable skeletal rearrangement into trichobrasilenol, a new brasilane sesquiterpene with one additional Me group equivalent compared to FPP. A mechanistic hypothesis for the formation of the brasilane skeleton is supported by extensive isotopic labelling studies.
