CARYOPHYLLENE OXIDE
Synonym(s):β-Caryophyllene epoxide;(−)-Epoxycaryophyllene;(−)-Epoxydihydrocaryophyllene;(1R,4R,6R,10S)-9-Methylene-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]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: 2024-08-05 20:55:42
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. |
Computed Descriptors for CARYOPHYLLENE OXIDE
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