Chemical Properties
Caryophyllene oxide is a Colorless or white crystalline powder that has a woody, slightly ambergris-like odor, can be prepared by treatment of β-caryophyllene with organic peracids.
Occurrence
Reported found in Nepeta betonicifolia C.A. Meyer oil Turkey (39.20%), geranium rose-scented oil (Pelargonium
spp.) Cuba (14.70%), melissa oil (9.99%), guava leaf oil Cuba (8.20%), etc.
Uses
β-Caryophyllene Epoxide, and its derivatives has shown to have microbial transformation and butyrylcholinesterase inhibitory activity. It is also the main active constituent of essential oils obtained from various plants, used for flavoring and fragrances.
Definition
ChEBI: Caryophyllene oxide is an epoxide，a natural product found in Cupania cinerea. It has a role as a metabolite.
Aroma threshold values
Medium strength odor, woody type.
Biological Activity
β-caryophyllene oxide is a potent anti-cancer agent which also exerts antioxidant, anti-inflammatory, and antiviral properties. It is a strong inhibitor of drug-metabolizing enzyme cytochromes P4503A (CYP3A) activities both in r at and human hepatic microsomes. BCPO also exerts analgesic, antifungal, antibacterial, and genoprotective activities.
Safety Profile
Low toxicity by
ingestion and skin contact. A skin irritant.
When heated to decomposition it emits
acrid smoke and irritating fumes.
Purification Methods
Purify the oxide by TLC on silica gel with EtOAc/pet ether (b 60-80o) (15:85), and recrystallise it from MeOH or *C6H6. [NMR: Warnhoff Can J Chem 42 1664 1964, Ramage & Whitehead J Chem Soc 4336 1954, Beilstein 17 IV 392.]
