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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H24O
Molecular Weight 220.351
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .BETA.-CARYOPHYLLENE OXIDE

SMILES

C=C1CC[C@]2([H])[C@@](C)(CC[C@]3([H])[C@]1([H])CC3(C)C)O2

InChI

InChIKey=NVEQFIOZRFFVFW-RGCMKSIDSA-N
InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C15H24O
Molecular Weight 220.351
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Natural bicyclic sesquiterpenes, β‐caryophyllene (BCP) and β‐caryophyllene oxide (BCPO), are present in a large number of plants worldwide. Both BCP and BCPO possess significant anticancer activities, affecting growth and proliferation of numerous cancer cells. BCP is a phytocannabinoid with strong affinity to cannabinoid receptor type 2 (CB2 ), but not cannabinoid receptor type 1 (CB1 ). In opposite, BCP oxidation derivative, BCPO, does not exhibit CB1/2 binding, thus the mechanism of its action is not related to endocannabinoid system (ECS) machinery. It is known that BCPO alters several key pathways for cancer development, such as mitogen-activated protein kinase (MAPK), PI3K/AKT/mTOR/S6K1 and STAT3 pathways. In addition, treatment with this compound reduces the expression of procancer genes/proteins, while increases the levels of those with proapoptotic properties. Either as a pure substance or a component of plant essential oils, BCPO was found to exhibit antiinflammatory, antioxidant, antiviral, anticarcinogenic, and analgesic properties. β-caryophyllene oxide evidenced potent cytotoxic activity against HepG2, AGS, HeLa, SNU-1, and SNU-16 cells, with IC50 values of 3.95, 12.6, 13.55, 16.79, and 27.39 uM, respectively.

CNS Activity

Curator's Comment:: β‐caryophyllene oxide it may possess some antinociceptive properties since Chavan et al. have documented centrally and peripherally mediated analgesia by BCPO isolated from Annona squamosa bark extract, in response to pain stimuli in mice

Approval Year

PubMed

PubMed

TitleDatePubMed
β-Caryophyllene oxide potentiates TNFα-induced apoptosis and inhibits invasion through down-modulation of NF-κB-regulated gene products.
2014 Apr
The Influence of Sesquiterpenes from Myrica rubra on the Antiproliferative and Pro-Oxidative Effects of Doxorubicin and Its Accumulation in Cancer Cells.
2015 Aug 21
β-caryophyllene and β-caryophyllene oxide-natural compounds of anticancer and analgesic properties.
2016 Oct
Patents

Sample Use Guides

Mice were treated with a combination of DOX + β‐caryophyllene oxide (CAO) (single i.v. dose of DOX 3 mg/kg and p.o. dose of CAO 50 mg/kg); mice were treated with a combination of DOX + CAO (single i.v. dose of DOX 3 mg/kg and p.o. dose of CAO 100 mg/kg).
Route of Administration: Other
In Vitro Use Guide
Curator's Comment:: CaCo-2 cancer cells were incubated with DOX alone (concentrations 0.25, 0.5, 1, 2, 4 uM), with individual β‐caryophyllene oxide alone (concentrations 6.125, 12.5, 25, 50 ug/mL) and with DOX (concentrations 0.25, 0.5, 1, 2 uM) in combinations with β‐caryophyllene oxide (concentrations 6.125, 12.5, 25, 50 ug/mL).
β‐caryophyllene oxide was able to significantly ameliorate DOX toxicity at concentrations 0.25 and 2 uM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:05:10 UTC 2021
Edited
by admin
on Sat Jun 26 07:05:10 UTC 2021
Record UNII
S2XU9K448U
Record Status Validated (UNII)
Record Version
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Name Type Language
.BETA.-CARYOPHYLLENE OXIDE
FHFI  
Common Name English
4.BETA.,5.ALPHA.-EPOXYCARYOPHYLLENE
Common Name English
(-)CAROPHYLLENE OXIDE
Common Name English
5-OXATRICYCLO(8.2.0.04,6)DODECANE, 4,12,12-TRIMETHYL-9-METHYLENE-, (1R-(1R*,4R*,6R*,10S*))-
Common Name English
CARYOPHYLLENE OXIDE
Common Name English
TRANS-CARYOPHYLLENE OXIDE
Common Name English
CARYOPHYLLENE, EPOXIDE
Common Name English
CARYOPHYLLENE 4.BETA.,5.ALPHA.-OXIDE
Common Name English
4-12,12-TRIMETHYL-9-METHYLENE-5-OXATRICYLO (8.2.0.04,6) DODECANE
Common Name English
(-)-.BETA.-CARYOPHYLLENE EPOXIDE
Common Name English
CARYOPHYLLENE 4.BETA.,5.ALPHA.-EPOXIDE
Common Name English
FEMA NO. 4085
Code English
(-)-BETA-CARYOPHYLLENE EPOXIDE [HSDB]
Common Name English
.BETA.-CARYOPHYLLENE OXIDE [FHFI]
Common Name English
5-OXATRICYCLO(8.2.0.04,6)DODECANE, 4,12,12-TRIMETHYL-9-METHYLENE-, (1R,4R,6R,10S)-
Systematic Name English
(-)-CARYOPHYLLENE OXIDE
Common Name English
Classification Tree Code System Code
JECFA EVALUATION BETA-CARYOPHYLLENE OXIDE
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
CFR 21 CFR 172.515
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
Code System Code Type Description
CAS
1139-30-6
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
PRIMARY
CAS
52209-95-7
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
SUPERSEDED
ECHA (EC/EINECS)
214-519-7
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
PRIMARY
MESH
C515179
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
PRIMARY
HSDB
5466
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
PRIMARY
PUBCHEM
1742210
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
PRIMARY
EPA CompTox
1139-30-6
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
PRIMARY
CAS
32095-03-7
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
SUPERSEDED
CAS
11023-55-5
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
SUPERSEDED
RXCUI
2395801
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
PRIMARY
CAS
105120-46-5
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
SUPERSEDED
FDA UNII
S2XU9K448U
Created by admin on Sat Jun 26 07:05:10 UTC 2021 , Edited by admin on Sat Jun 26 07:05:10 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Sesquiterpene Class