CAS Number87-44-5
Synonyms[1R-(1R*,4E,9S*)]-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; trans-Caryophyllene; β-caryophyllene; MFCD00075925; (-)-trans-Caryophyllene; (1R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; Caryophyllene (VAN); (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene; EINECS 201-746-1; l-Caryophyllene; (-)-beta-caryophyllene; (-)-Caryophyllene; β-(E)-Caryophyllene; Caryophyllene; (E)-Caryophyllene
Molecular FormulaC15H24
Molecular Weight204.35
Purity≥80%
Density0.9±0.1 g/cm3
Boiling Point129-130 °C/14 mmHg (lit.)
AppearanceLight yellow oily liquid with an odor between clove and rosin
EINECS201-746-1
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Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 87-44-5 |
| Catalog No. | 2A-9009612 |
| Chinese Name | 反式石竹烯 |
| Synonyms | [1R-(1R*,4E,9S*)]-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; trans-Caryophyllene; β-caryophyllene; MFCD00075925; (-)-trans-Caryophyllene; (1R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; Caryophyllene (VAN); (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene; EINECS 201-746-1; l-Caryophyllene; (-)-beta-caryophyllene; (-)-Caryophyllene; β-(E)-Caryophyllene; Caryophyllene; (E)-Caryophyllene |
| Molecular Formula | C15H24 |
| Molecular Weight | 204.35 |
| Purity | ≥80 |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 129-130 °C/14 mmHg (lit.) |
| Appearance | Light yellow oily liquid with an odor between clove and rosin |
| Storage Condition | Sealed packaging in brown glass bottles. Store in |
| Application | Beta-Caryophyllene is a CB2 receptor agonist. |
| EINECS | 201-746-1 |
| HTC | 2902199090 |
| PubChem ID | 24900952 |
| MDL Number | MFCD00075925 |
| SMILES | C\C1=C/CCC(=C)[C@H]2CC(C)(C)[C@@H]2CC1 |
| InChI | 1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1 |
| InChI Key | NPNUFJAVOOONJE-GFUGXAQUSA-N |
| Beilstein/REAXYS | 2044564 |
| NACRES Code | NA.21 |
| UNSPSC | 12164502 |
| Hazard Symbols | Transport |
| Bioactivity | β-Caryophyllene is a CB2 receptor agonist. Related Catalog Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor Research Areas >> Cancer Research Areas >> Infection Research Areas >> Neurological Disease Natural Products >> Terpenoids and Glycosides Target CB2 receptor[1] In Vitro Among the tested cancer cells, β-Caryophyllene demonstrates selective anti-proliferative effect against three 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[2]. In Vivo Treatment with β-Caryophyllene at different doses does not show any effects on swimming speed during the test. Oral treatment with β-Caryophyllene ameliorates the rise in β-amyloid deposition in the transgenic mice in a roughly dose-dependent manner, and the two higher doses exhibit almost equal effects in modifying the β-amyloid burden. The number of activated astroglial cells is higher in vehicle-treated mouse brains than in β-Caryophyllene-treated mouse brains with different doses. β-Caryophyllene is effective at reducing the enhancement of the COX-2 protein level found in vehicle-treated APP/PS1 mice[1]. Animals treated with β-Caryophyllene display higher values of object recognition index than their vehicle-treated counterparts [t(14)=4.204, P<0.05]. The total time spent in object exploration during the test trial is not significantly different between β-Caryophyllene-treated and vehicle-treated animals (t(14)=0.5874, P>0.05). Treatment with β-Caryophyllene does not significantly alter these seizure-induced neurochemical changes[3]. Cell Assay 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[2]. Animal Admin 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[1]. References [1]. Cheng Y, et al. 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, et al. 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, et al. Anticonvulsant activity of β-caryophyllene against pentylenetetrazol-induced seizures. Epilepsy Behav. 2016 Mar;56:26-31. Chemical & Physical Properties Density 0.9±0.1 g/cm3 Boiling Point 268.4±10.0 °C at 760 mmHg Molecular Formula C15H24 Molecular Weight 204.351 Flash Point 104.9±13.8 °C Exact Mass 204.187805 LogP 6.78 Vapour Pressure 0.0±0.3 mmHg at 25°C Index of Refraction 1.495 InChIKey NPNUFJAVOOONJE-QWAJQTJBSA-N SMILES C=C1CCC=C(C)CCC2C1CC2(C)C |
| Use of | β-Caryophyllene is a CB2 receptor agonist. Properties Articles29 Name (-)-β-caryophyllene Synonym More Synonyms trans-Caryophyllene Biological Activity Description β-Caryophyllene is a CB2 receptor agonist. Related Catalog Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor Research Areas >> Cancer Research Areas >> Infection Research Areas >> Neurological Disease Natural Products >> Terpenoids and Glycosides CB2 receptor[1] References [1]. Cheng Y, et al. 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, et al. 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, et al. Anticonvulsant activity of β-caryophyllene against pentylenetetrazol-induced seizures. Epilepsy Behav. 2016 Mar;56:26-31. Chemical & Physical Properties Molecular Formula C15H24 Exact Mass 204.187805 Index of Refraction 1.495 InChIKey NPNUFJAVOOONJE-QWAJQTJBSA-N |
| Tax Rebate | 9.0% |
| Supervision | none |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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