CARYOPHYLLENE OXIDE

Synonym(s):β-Caryophyllene epoxide;(−)-Epoxycaryophyllene;(−)-Epoxydihydrocaryophyllene;(1R,4R,6R,10S)-9-Methylene-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^4,6]dodecane;trans-Caryophyllene oxide

CAS NO.：1139-30-6
Empirical Formula: C15H24O
Molecular Weight: 220.35
MDL number: MFCD00134216
EINECS: 214-519-7
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-19 23:02:33

What is CARYOPHYLLENE OXIDE?

Chemical properties

white crystalline powder

Chemical properties

Caryophyllene oxide which has a woody, slightly ambergris-like odor, can be prepared by treatment of ??-caryophyllene with organic peracids.

Chemical properties

Colorless solid; sweet fruity aroma.

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.

The Uses of CARYOPHYLLENE OXIDE

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.

What are the applications of Application

(?)-Caryophyllene oxide is a carefully purified sesquiterpene

Definition

ChEBI: A natural product found in Cupania cinerea.

Aroma threshold values

Medium strength odor, woody type.

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.]

Properties of CARYOPHYLLENE OXIDE

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
optical activity	[α]20/D 71±1°, c = 2% in chloroform
Water Solubility	insoluble in water
JECFA Number	1575
BRN	148213
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 for CARYOPHYLLENE OXIDE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07 Environment GHS09
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H411:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P273:Avoid release to the environment. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.