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β-Caryophyllene

Catalog No. T9114   CAS 87-44-5
Synonyms: (-)-(E)-Caryophyllene, (−)-β-caryophyllene, (−)-trans-Caryophyllene

β-Caryophyllene ((-)-(E)-Caryophyllene) acts as an CB2 receptor agonist.

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β-Caryophyllene Chemical Structure
β-Caryophyllene, CAS 87-44-5
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Purity: 99.11%
Purity: 97.31%
Purity: 95.43%
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Biological Description
Chemical Properties
Storage & Solubility Information
Description β-Caryophyllene ((-)-(E)-Caryophyllene) acts as an CB2 receptor agonist.
In vitro β-Caryophyllene demonstrates selective anti-proliferative effects against among the three tested cancer cell lines, namely HCT 116 (colon cancer, IC50=19 μM), PANC-1 (pancreatic cancer, IC50=27 μM), and HT29 (colon cancer, IC50=63 μM) cells, whereas β-Caryophyllene exhibits either moderate or poor cytotoxic effects against ME-180, PC3, K562 and MCF-7. Results show that β-Caryophyllene possesses higher selectivity towards the colorectal cancer cells (HCT 116), with selectivity index (SI)=27.9, followed by PANC-1 and HT 29 cells with SI=19.6 and 8, respectively. The apoptotic index estimated for β-Caryophyllene treatment on HCT 116 cells after 24 h treatment is 64±0.04. β-Caryophyllene at 10 μM concentration, causes significant nuclei condensation after 6 h of treatment. β-caryophyllene exhibits a dose and time-dependent inhibitory effect on the motility of HCT 116 cells.
In vivo During the examination period, administering varying doses of β-Caryophyllene had no impact on swimming speed. However, oral administration of β-Caryophyllene significantly reduced β-amyloid deposition in transgenic mice in a nearly dose-dependent manner, with the two highest doses showing comparable efficacy in decreasing β-amyloid accumulation. Notably, vehicle-treated mice displayed an increased number of activated astroglial cells compared to those treated with any dose of β-Caryophyllene. Furthermore, β-Caryophyllene effectively lowered the elevated COX-2 protein levels observed in vehicle-treated APP/PS1 mice. Additionally, animals receiving β-Caryophyllene treatment demonstrated a higher object recognition index than their vehicle-treated counterparts, indicating improved memory retention [t(14)=4.204, P<0.05]. There was no significant difference in the total time spent exploring objects between the β-Caryophyllene and vehicle-treated groups during the test trial (t(14)=0.5874, P>0.05). β-Caryophyllene treatment did not significantly affect seizure-induced neurochemical alterations.
Cell Research Stock solution (10 mM) of β-Caryophyllene is prepared using DMSO. Further, various concentrations (3 to 100 μM) of β-Caryophyllene are prepared by serially diluting the stock with respective culture medium.Panel of human cancer cells such as, pancreatic (PANC-1), colorectal (HCT-116 and HT-29), invasive squamous cell carcinoma (ME-180), leukemia (K562), hormone sensitive and invasive breast cancer cell line (MCF-7), and prostatic (PC3) adenocarcinoma cell lines are used. Cells are incubated in a humidified CO2 incubator at 37°C supplied with 5% CO2. Inhibitory effect of β-Caryophyllene on proliferation of the cell lines is tested using the MTT assay. The selectivity index (SI) for the cytotoxicity of β-Caryophyllene is calculated using the ratio of IC50 of β-Caryophyllene on a normal cell line (NIH-3T3) to the IC50 of β-Caryophyllene on cancer cell lines. They are for reference only.
Animal Research β-Caryophyllene is initially dissolved in dimethyl sulfoxide and further diluted (2%) in sterile phosphate-buffered saline (PBS) with 10% Cremophor EL (poluoxyl-35 hydrogenated castor oil).Male double transgenic APP/PS1 mice and wild-type littermates are used. The mice are group housed (3 to 5 animals/cage) with a 12:12-hour light/dark cycle and ad libitum access to food and water. In this experiment, animals are orally treated by gavage with 16, 48, or 144 mg/kg of β-Caryophyllene every morning for 10 weeks starting at the age of 7 months. All vehicle solutions are used for the respective control animal treatments and the Morris water maze test is performed. They are for reference only.
Source
Synonyms (-)-(E)-Caryophyllene, (−)-β-caryophyllene, (−)-trans-Caryophyllene
Molecular Weight 204.35
Formula C15H24
CAS No. 87-44-5

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

DMSO: < 1 mg/mL (insoluble or slightly soluble)

Ethanol: 176.67 mg/mL (864.55 mM)

H2O: < 0.1 mg/mL (insoluble)

TargetMolReferences and Literature

1. Cheng Y, etal. β-Caryophyllene ameliorates the Alzheimer-like phenotype in APP/PS1 Mice through CB2 receptor activation and the PPARγ pathway. Pharmacology. 2014;94(1-2):1-12. 2. Dahham SS, etal. The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllenefrom the Essential Oil of Aquilaria crassna. Molecules. 2015 Jun 26;20(7):11808-29. 3. de Oliveira CC, etal. Anticonvulsant activity of β-caryophyllene against pentylenetetrazol-induced seizures. Epilepsy Behav. 2016 Mar;56:26-31.

TargetMolCitations

1. Li W, Qian P, Guo Y, et al. Myrtenal and β-caryophyllene oxide screened from Liquidambaris Fructus suppress NLRP3 inflammasome components in rheumatoid arthritis. BMC complementary medicine and therapies. 2021, 21(1): 1-16.

Related compound libraries

This product is contained In the following compound libraries:
Natural Product Library Membrane Protein-targeted Compound Library Traditional Chinese Medicine Monomer Library Tobacco Monomer Library Miao medicine Compound Library Natural Product Library for HTS GPCR Compound Library Selected Plant-Sourced Compound Library Bioactive Compounds Library Max Human Metabolite Library

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Keywords

β-Caryophyllene 87-44-5 GPCR/G Protein Metabolism Cannabinoid Receptor Endogenous Metabolite βCaryophyllene β Caryophyllene inhibit (-)-(E)-Caryophyllene Inhibitor Caryophyllene beta-Caryophyllene (−)-β-caryophyllene (−)-trans-Caryophyllene (−)-beta-caryophyllene b-Caryophyllene (−)-b-caryophyllene inhibitor

 

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