87-44-5 Usage
Description
β-Caryophyllene (Item No. 21572) 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. It is an agonist of the cannabinoid (CB) receptor CB2 (Ki = 155 nM) that inhibits cAMP production induced by forskolin in CHO-K1 cells expressing CB2 receptors (EC50 = 38 nM). β-Caryophyllene is also an agonist of peroxisome proliferator-activated receptor α (PPARα; EC50 = 9.58 μM in a reporter assay). β-Caryophyllene (1 and 2.5 μM) reduces the production of reactive oxygen species (ROS) in and protects 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 and improves memory in an APP/PS1 transgenic mouse model of Alzheimer’s disease, decreasing the latency to find the platform in the Morris water maze during training and increasing the time spent in the target quadrant during testing when administered at a dose of 48 mg/kg per day. β-Caryophyllene (50 mg/kg) increases 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, indicating anxiolytic-like and antidepressant-like activity, effects that can be blocked by the CB2 receptor antagonist AM630 .
Chemical Properties
Different sources of media describe the Chemical Properties of 87-44-5 differently. You can refer to the following data:
1. Clear colorless liquid
2. 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
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
General Description
Pale yellow oily liquid with an odor midway between odor of cloves and turpentine.
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)
COMPOSITIONS HAVING AN AGENT AND AN ENHANCER THEREOF, METHODS OF USE, AND DELIVERY SYSTEMS
-
, (2020/03/23)
The present invention relates to compositions, and methods of use thereof, related to the endocannabinoid system and includes therapeutic compositions including an agent and an enhancer thereof, optionally, formulated for administration of the therapeutic compositions, preferably in a measured amount.
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.
