CAS 87-44-5|trans-Caryophyllene
Introduction：Basic information about CAS 87-44-5|trans-Caryophyllene, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | trans-Caryophyllene | ||
|---|---|---|---|
| CAS Number | 87-44-5 | Molecular Weight | 204.351 |
| Density | 0.9±0.1 g/cm3 | Boiling Point | 268.4±10.0 °C at 760 mmHg |
| Molecular Formula | C15H24 | Melting Point | / |
| MSDS | ChineseUSA | Flash Point | 104.9±13.8 °C |
Names
| Name | (-)-β-caryophyllene |
|---|---|
| Synonym | More Synonyms |
trans-Caryophyllene BiologicalActivity
| Description | β-Caryophyllene is a CB2 receptor agonist. |
|---|---|
| Related Catalog | Signaling Pathways >>GPCR/G Protein >>Cannabinoid ReceptorResearch Areas >>CancerResearch Areas >>InfectionResearch Areas >>Neurological DiseaseNatural 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- Standard Draize test
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Rodent - rabbit
- REFERENCE :
- FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 11,1059,1973 ** ACUTE TOXICITY DATA **
- TYPE OF TEST :
- LD - Lethal dose
- ROUTE OF EXPOSURE :
- Intratracheal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >48 mg/kg
- TOXIC EFFECTS :
- Lungs, Thorax, or Respiration - pulmonary emboli
- REFERENCE :
- ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 59,78,1986 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X7407 No. of Facilities: 3144 (estimated) No. of Industries: 10 No. of Occupations: 18 No. of Employees: 44746 (estimated) No. of Female Employees: 27262 (estimated)
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves |
|---|---|
| Hazard Codes | Xi |
| Risk Phrases | 36/37/38 |
| Safety Phrases | S26-S36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 1 |
| RTECS | DT8400000 |
| HS Code | 2902199090 |
Customs
| HS Code | 2902199090 |
|---|---|
| Summary | 2902199090 other cyclanes, cyclenes and cyclotherpenes。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:2.0%。General tariff:30.0% |
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Synonyms
| [1R-(1R*,4E,9S*)]-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene |
| Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- |
| 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 |
| Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,9S)- |
| Bicyclo(7.2.0)undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)- |
| Bicyclo[7.2.0]undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)- |
| Caryophyllene |
| (E)-Caryophyllene |
