ChemicalBook Product Catalog Flavors and fragrances Synthetic fragrances Phenols, ethers and epoxides Epoxide Caryophyllene oxide

Caryophyllene oxide

Product NameCaryophyllene oxide
CAS1139-30-6
MFC15H24O
MW220.35
EINECS214-519-7
MOL File1139-30-6.mol

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
Major Application	metabolomics vitamins, nutraceuticals, and natural products
Cosmetics Ingredients Functions	PERFUMING
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
InChIKey	NVEQFIOZRFFVFW-RGCMKSIDSA-N
SMILES	[H][C@@]12CCC(=C)[C@@]3([H])CC(C)(C)[C@]3([H])CC[C@@]1(C)O2
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
TSCA	TSCA listed
HS Code	29109000
Storage Class	11 - Combustible Solids
Hazard Classifications	Aquatic Chronic 2 Eye Irrit. 2 Skin Irrit. 2
Hazardous Substances Data	1139-30-6(Hazardous Substances Data)

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English

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.]

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