trans-Caryophyllene

Names

[ CAS No. ]:
87-44-5

[ Name ]:
trans-Caryophyllene

[Synonym ]:
[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

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

[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.

[Related Small Molecules]

WIN 55212-2 mesylate | AM251 | Taranabant | SR144528 | Bay 59-3074 | Org 27569 | Otenabant | GW842166X | A-836339 | BML-190 | JD-5037 | (±)-SLV319 | Pregnenolone | Anandamide | 2-arachidonoylglycerol

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

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DT8400000

CHEMICAL NAME :: Bicyclo(7.2.0)undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-

CAS REGISTRY NUMBER :: 87-44-5

LAST UPDATED :: 199712

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C15-H24

MOLECULAR WEIGHT :: 204.39

WISWESSER LINE NOTATION :: L49 EY HUTJ B1 B1 EU1 I1

HEALTH HAZARD DATA

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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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