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| | CARYOPHYLLENE OXIDE Basic information |
| Product Name: | CARYOPHYLLENE OXIDE | | Synonyms: | (-)-5-Oxatricyclo[8.2.0.0(4,6)]dodecane,4,12,12-trimethyl-9-methylene-, [1R-(1R*,4R*,6R*,10S*)]-;caryophylleneepoxide;(1R,4R,6R,10S)-9-METHYLENE-4,12,12-TRIMETHYL-5-OXATRICYCLO[8.2.0.0(4,6)]DODECANE;CARYOPHYLLENE OXIDE;caryophylleneoxide,(1R,4R,6R,10S)-4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.0]4,6)]dodecane;5-Oxatricyclo8.2.0.04,6dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)-;(1R-(1R*,4R*,6R*,10S*))-4,12,12-Trimethyl-9-methylen-5-oxatricyclo(8.2.0.04,6)dodecan;(-)-Epoxycaryophyllene, (1R,4R,6R,10S)-9-Methylene-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecane | | CAS: | 1139-30-6 | | MF: | C15H24O | | MW: | 220.35 | | EINECS: | 214-519-7 | | Product Categories: | Sesquiterpenoids;Inhibitors;Alphabetical Listings;C-D;Flavors and Fragrances | | Mol File: | 1139-30-6.mol |  |
| | 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 | | Fp | >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 | | 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) |
| | CARYOPHYLLENE OXIDE Usage And Synthesis |
| Chemical Properties | Colorless solid; sweet fruity aroma. | | 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. | | 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: 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.] |
| | CARYOPHYLLENE OXIDE Preparation Products And Raw materials |
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