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87-44-5

87-44-5 structure
87-44-5 structure
Name (-)-β-caryophyllene
Synonyms β-cyophyllene,[1R-(1R,4E,9S)]-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene,(E)-cyophyllene
beta-ciofillene
(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
TRANS-CYOPHYLLENE
(-)-TRANS-CYOPHYLLENE
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]
(1R,4E,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
4,11,11-trimethyl-8-methylene-,(1r-(1r*,4e,9s*))-bicyclo(7.2.0)undec-4-en
Bicyclo(7.2.0)undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)
8-methylene-4,11,11-trimethyl-,(e)-(1r,9s)-(-)-bicyclo(7.2.0)undec-4-en
BetaCryophellene
8-METHYLENE-4,11,11-TRIMETHYLBICYCLO-UNDEC-4-ENE
B-CYOPHYLLENE, NATURAL
L-Cyophyllene
CYOPHYLLENE, (-)-TRANS
8-METHYLENE-4,11,11-TRIMETHYLBICYCLO[7.2.0]UNDEC-4-ENE
(E)-Caryophyllene
β-Cyophyllene, trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
β-caryophyllene
Eugenol Impurity 1（Eugenol Impurity A）
bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-,(E)-(1R,9S)-(-)
(-)-trans-Caryophyllene
[1R-(1R*,4E,9S*)]-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]-4-undecene
(1R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
l-Caryophyllene
E-beta-cyophyllene
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (E)-(1R,9S)-(-)
BETA-CYOPHYLLEN
HUMULENE, alpha-(SG)
NATURAL β-CYOPHYLLENE
(-)-Caryophyllene
β-(E)-Caryophyllene
TRANS-(1R,9S)-8-METHYLENE-4,11,11-TRIMETHYLBICYCLO[7.2.0]UNDEC-4-ENE
Caryophyllene
CYOPHYLLENE, (-)-trans-(SG)
(1R,9S)-8-METHYLEN-4,11,11-TRIMETHYL-BICYCLO[7.2.0]UNDEC-4-ENE
trans-beta-cyophyllene
(-)-E-cyophyllene
8-METHYLENE-4,11,11-TRIMETHYLBICYCLO[7.2.0]UNDEC-4-ENE FCC
(-)-trans-Cyophyllene, trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
Soluble Cyophyllene, Liposomal Cyophyllene, Cyophyllene NanoEmulsion
[1R-(1R*,4E,9S*)]-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
(-)-TRANS-CYOPHYLLENE WITH
Bicyclo7.2.0undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)
CYOPHYLLENE
CYOPHYLLENE NATURAL
Caryophyllene (VAN)
CYOPHYLLEN BETA NATUERLICH
EINECS 201-746-1
4,11,11-trimethyl-8-methylene-,[1R-(1R*,4E,9S*)]-Bicyclo[7.2.0]undec-4-ene
Cyophyllene (E)
1-cyophyllene
COPHYLENE
B-CYOPHYLLENE
β-cyophyllen
(E)-Cyophyllene
beta-(E)-Cyophyllene
MFCD00075925
BETA-CYOPHYLLENE
2-Methylene-6,10,10-trimethyl bicyclo[7.2.0]undec-5-ene
[1R-(1R*,4E,9S*)]-8-methylene-4,11,11-trimethylbicyclo[7.2.0]-4-undecane
(-)-beta-caryophyllene
BETA-CYOPHYLLENE FCC
beta-Cyophyllene solution
beta-trans-cyophyllene
CYOPHYLLENE ,alpha + beta MIXT
(E)-beta-Cyophylene
BETA-CYPOPHYLLENE
Eugenol Impurity A
t-.beta.-cyophyllene
(-) TRANS CYOPHYLLEN
Description β-Caryophyllene is a CB2 receptor agonist.
Related Catalog
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

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
60362-44-9 structure

60362-44-9

1779-49-3 structure

1779-49-3

~80%

87-44-5 structure

87-44-5

Literature: Larionov, Oleg V.; Corey Journal of the American Chemical Society, 2008 , vol. 130, # 10 p. 2954 - 2955
65563-95-3 structure

65563-95-3

~10%

87-44-5 structure

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
60594-22-1 structure

60594-22-1

~%

87-44-5 structure

87-44-5

122571-86-2 structure

122571-86-2

86834-01-7 structure

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
60594-22-1 structure

60594-22-1

~%

87-44-5 structure

87-44-5

136296-35-0 structure

136296-35-0

136296-38-3 structure

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
60594-22-1 structure

60594-22-1

~%

87-44-5 structure

87-44-5

118-65-0 structure

118-65-0

136296-35-0 structure

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
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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