Chemical Property of Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
Chemical Property:
- Appearance/Colour:Pale yellow oily liquid with an odor midway between odor of cloves and turpentine.
- Vapor Pressure:0.0453mmHg at 25°C
- Melting Point:<25℃
- Refractive Index:n20/D 1.5(lit.)
- Boiling Point:268.359 °C at 760 mmHg
- Flash Point:104.917 °C
- PSA：0.00000
- Density:0.894 g/cm3
- LogP:4.72520
- Storage Temp.:2-8°C
- Solubility.:Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
- Water Solubility.:<0.1 g/100 mL at 21 C
- XLogP3:4.4
- Hydrogen Bond Donor Count:0
- Hydrogen Bond Acceptor Count:0
- Rotatable Bond Count:0
- Exact Mass:204.187800766
- Heavy Atom Count:15
- Complexity:293
- Purity/Quality:
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HPLC≥98% *data from raw suppliers
β-Caryophyllene *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:
- Statements:
36/37/38
- Safety Statements:
26-36-24/25
- MSDS Files:
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SDS file from LookChem
Total 1 MSDS from other Authors
Useful:
- Chemical Classes:Biological Agents -> Plant Oils and Extracts
- Canonical SMILES:CC1=CCCC(=C)C2CC(C2CC1)(C)C
- Isomeric SMILES:CC1=CCCC(=C)[C@H]2CC([C@@H]2CC1)(C)C
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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 .
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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.
