| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H24O |
| Molecular Weight | 220.3505 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2
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
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
Originator
Approval Year
PubMed
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
SUBSTANCE RECORD
