trans-Caryophyllene

Modify Date: 2024-01-02 19:29:56

trans-Caryophyllene structure	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	N/A
	MSDS	Chinese USA	Flash Point	104.9±13.8 °C

Use of trans-Caryophyllene

β-Caryophyllene is a CB2 receptor agonist.

Name	(-)-β-caryophyllene
Synonym	More Synonyms

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.

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

trans-Caryophyllene MSDS(Chinese)

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)

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

(1S,9R)-6,10,10...

CAS#:60362-44-9

Methyltriphenyl...

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~80%

trans-Caryophyllene

CAS#:87-44-5

Literature: Larionov, Oleg V.; Corey Journal of the American Chemical Society, 2008 , vol. 130, # 10 p. 2954 - 2955

4,5-epithiocary...

CAS#:65563-95-3

~10%

trans-Caryophyllene

CAS#:87-44-5

Literature: Peppard, Terence L.; Sharpe, F. Richard; Elvidge, John A. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 311 - 313

β-caryophyllene...

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trans-Caryophyllene

CAS#:87-44-5

N/A

CAS#:122571-86-2

4,5-dihydrocary...

CAS#:86834-01-7

Detail

Literature: Journal of Organic Chemistry USSR (English Translation), , vol. 25, # 1.2 p. 109 - 118 Zhurnal Organicheskoi Khimii, , vol. 25, # 1 p. 122 - 132

β-caryophyllene...

CAS#:60594-22-1

trans-Caryophyllene

CAS#:87-44-5

(1R,3Z,9S)-4,11...

CAS#:136296-35-0

10,10-dimethyl-...

CAS#:136296-38-3

Literature: Journal of Organic Chemistry USSR (English Translation), , vol. 26, # 10.2 p. 1839 - 1852 Zhurnal Organicheskoi Khimii, , vol. 26, # 10 p. 2129 - 2145

β-caryophyllene...

CAS#:60594-22-1

trans-Caryophyllene

CAS#:87-44-5

isocaryophyllene

CAS#:118-65-0

(1R,3Z,9S)-4,11...

CAS#:136296-35-0

Detail

Literature: Journal of Organic Chemistry USSR (English Translation), , vol. 26, # 10.2 p. 1839 - 1852 Zhurnal Organicheskoi Khimii, , vol. 26, # 10 p. 2129 - 2145

Precursor 3
CAS#:60362-44-9 (1S,9R)-6,10,10... CAS#:1779-49-3 Methyltriphenyl... CAS#:60594-22-1 β-caryophyllene...
DownStream 10
CAS#:58404-89-0 (1alpha,2alpha,... CAS#:469-92-1 (-)-CLOVENE CAS#:31887-51-1 (1R,2S,7S,9R)-2... CAS#:4545-68-0 (-)-ALPHA-[1-(D...
CAS#:6753-98-6 Alpha-caryophyllene CAS#:95-13-6 Indene CAS#:86-73-7 9H FLUORENE CAS#:28834-17-5 4,11,11-trimeth...
CAS#:129-00-0 Pyrene CAS#:597-43-3 2,2,-Dimethylsu...

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%

Chemical composition, antioxidant, and antimicrobial activities of essential oil from pine needle (Cedrus deodara).

J. Food Sci. 77(7) , C824-9, (2012)

The chemical composition of essential oil from pine needles (Cedrus deodara) was determined, and its antioxidant and antimicrobial activities were evaluated. Twenty-three components, representing 95.7...

Chemical diversity among the essential oils of wild populations of Stachys lavandulifolia VAHL (Lamiaceae) from Iran.

Chem. Biodivers. 10(2) , 262-73, (2013)

The variation of the essential-oil composition among ten wild populations of Stachys lavandulifolia VAHL (Lamiaceae), collected from different geographical regions of Iran, was assessed by GC-FID and ...

Chemical composition and biological activities of soldiers of the Brazilian termite species, Nasutitermes macrocephalus (Isoptera: Natutitermitinae).

Nat. Prod. Commun. 8(1) , 69-74, (2013)

The defensive secretion of the frontal gland from termite soldiers is a mixture of monoterpenes, sesquiterpenes and diterpenes, the latter being the most representative. Analyses of the dichloromethan...

[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

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China
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China
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