Caryophyllene oxide Chemical Properties

Melting point:

62-63 °C(lit.)

Boiling point:

301.3°C (rough estimate)

Density 

0.96

refractive index 

1.4956

FEMA 

4085 | BETA-CARYOPHYLLENE OXIDE

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Crystalline Powder

color 

White

Odor

at 100.00 %. sweet fresh dry woody spicy

Odor Type

woody

biological source

synthetic

optical activity

[α]20/D 71±1°, c = 2% in chloroform

Water Solubility 

insoluble in water

JECFA Number

1575

BRN 

148213

LogP

4.57

EPA Substance Registry System

5-Oxatricyclo[8.2.0.04,6]dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)- (1139-30-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26

WGK Germany 

2

RTECS 

RP5530000

F 

1-10

HS Code 

29109000

Hazardous Substances Data

1139-30-6(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Caryophyllene oxide Usage And Synthesis

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.]

Caryophyllene oxide(1139-30-6)Related Product Information

• alpha-Bisabolol
• Carbomer
• Ethanol
• Glycerol
• Salicylic acid
• Citric acid
• Centella asiatica whole plant
• Caryophyllene oxide
• β-Caryophyllene
• Dodecane
• ALPHA-CARYOPHYLLENE
• Methyl oleanolate
• (R)-(+)-1,2-EPOXY-9-DECENE
• Dihydromyrcenol
• 1,2-EPOXY-5-HEXENE
• (R)-(+)-1 2-EPOXYUNDECANE 97
• CARYOPHYLLENE OXIDE(RG)
• SODIUM OLEANOLATE