trans-Caryophyllene

Modify Date: 2026-07-01 17:11:54

trans-Caryophyllene Structure
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.

 Names

This table lists Chinese names, IUPAC names and various aliases of this chemical substance.

Name (-)-β-caryophyllene
Synonym More Synonyms

 trans-Caryophyllene Biological Activity

This table contains bioactivity, target information and biological‑assay experimental data of this compound.

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.

 Chemical & Physical Properties

This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.

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

 MSDS

This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.

 Toxicological Information

This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.

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

This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.

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

This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.

~80%

trans-Caryophyllene Structure

trans-Caryophyllene

CAS#:87-44-5

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

~10%

trans-Caryophyllene Structure

trans-Caryophyllene

CAS#:87-44-5

Learn More
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

~%

trans-Caryophyllene Structure

trans-Caryophyllene

CAS#:87-44-5

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

~%

trans-Caryophyllene Structure

trans-Caryophyllene

CAS#:87-44-5

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

~%

trans-Caryophyllene Structure

trans-Caryophyllene

CAS#:87-44-5

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

 Customs

This table shows customs‑related data including HS‑code, tariff and regulatory conditions for import and export.

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%

 Articles29

More Articles

This table lists relevant public references with title, journal and publication metadata for this compound.

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...

 trans-CaryophylleneBioassay

View more

This table contains target information, in‑vitro & in‑vivo assay data for this compound.

Name: p53 small molecule agonists, cell-based qHTS assay
Source: 824
External Id: P53344
Name: p53 small molecule agonists, cell-based qHTS assay with human liver microsomes
Source: 824
Target: tumor suppressor p53 [Homo sapiens]
External Id: P53MS233
Name: p53 small molecule agonists, cell-based qHTS assay with rat liver microsomes
Source: 824
Target: tumor suppressor p53 [Homo sapiens]
External Id: P53MS898
Name: Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Cac...
Source: ChEMBL
Target: Severe acute respiratory syndrome coronavirus 2
External Id: CHEMBL4303805
Name: SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response f...
Source: ChEMBL
Target: Replicase polyprotein 1ab
External Id: CHEMBL4495582
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 Synonyms

This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.

[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

 trans-Caryophyllene | FAQ

This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.

Q: What is the English name of (-)-β-caryophyllene?
A: The English name of (-)-β-caryophyllene is (-)-β-caryophyllene.
Q: What is the molecular weight of (-)-β-caryophyllene?
A: Molecular weight of (-)-β-caryophyllene is 204.351.
Q: What are the upstream materials of (-)-β-caryophyllene?
A: Related upstream materials(CAS) of (-)-β-caryophyllene: 60362-44-9;1779-49-3;60594-22-1.
Q: What English synonyms does (-)-β-caryophyllene have?
A: English synonyms of (-)-β-caryophyllene: [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.
Q: What is the CAS number of (-)-β-caryophyllene?
A: CAS number of (-)-β-caryophyllene is 87-44-5.
Q: What is the safety information for (-)-β-caryophyllene?
A: Safety information for (-)-β-caryophyllene: S26-S36.
Q: What are the downstream products of (-)-β-caryophyllene?
A: Related downstream products(CAS) of (-)-β-caryophyllene: 58404-89-0;469-92-1;31887-51-1;4545-68-0;6753-98-6;95-13-6;86-73-7;28834-17-5;129-00-0;597-43-3.
Q: What is the molecular formula of (-)-β-caryophyllene?
A: Molecular formula of (-)-β-caryophyllene is C15H24.
Q: What is the SMILES notation of (-)-β-caryophyllene?
A: SMILES notation of (-)-β-caryophyllene is C=C1CCC=C(C)CCC2C1CC2(C)C.
Q: What is the LogP of (-)-β-caryophyllene?
A: LogP of (-)-β-caryophyllene is 6.78.

 trans-Caryophyllenefactory

This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.

Shanghai Nianxing Industrial Co., Ltd
BioBioPha
Dayang Chem (Hangzhou) Co., Ltd.
Henan Tianfu Chemical Co., Ltd.
Zhongshan Xingrui Chemical Co. , Ltd.
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