[1R-(1R,4R,6R,10S)]-4,12,12-Trimethyl-9-methylen-5-oxatricyclo[8.2.0.04,6]dodecan

Bezeichnung:[1R-(1R*,4R*,6R*,10S*)]-4,12,12-Trimethyl-9-methylen-5-oxatricyclo[8.2.0.04,6]dodecan

Englisch Name:CARYOPHYLLENE OXIDE

CBNumberCB3199893

SummenformelC15H24O

Molgewicht220.35

Synonyma

[1R-(1R*,4R*,6R*,10S*)]-4,12,12-Trimethyl-9-methylen-5-oxatricyclo[8.2.0.04,6]dodecan

[1R-(1R*,4R*,6R*,10S*)]-4,12,12-Trimethyl-9-methylen-5-oxatricyclo[8.2.0.04,6]dodecan physikalisch-chemischer Eigenschaften

Schmelzpunkt	62-63 °C(lit.)
Siedepunkt	301.3°C (rough estimate)
Dichte	0.96
Brechungsindex	1.4956
FEMA	4085 \| BETA-CARYOPHYLLENE OXIDE
Flammpunkt	>230 °F
storage temp.	2-8°C
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand	Crystalline Powder
Farbe	White
Geruch (Odor)	at 100.00 %. sweet fresh dry woody spicy
Geruchsart	woody
Optische Aktivität	[α]20/D 71±1°, c = 2% in chloroform
Wasserlöslichkeit	insoluble in water
JECFA Number	1575
BRN	148213
LogP	4.57
EPA chemische Informationen	5-Oxatricyclo[8.2.0.04,6]dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)- (1139-30-6)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/38
S-Sätze:	26
WGK Germany	2
RTECS-Nr.	RP5530000
F	1-10
HS Code	29109000
Giftige Stoffe Daten	1139-30-6(Hazardous Substances Data)

Gefahreninformationscode (GHS)

R-Sätze Betriebsanweisung:
R36/38:Reizt die Augen und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
Colorless solid; sweet fruity aroma.
Chemische Eigenschaften
white crystalline powder
Chemische Eigenschaften
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.
Verwenden
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.
Sicherheitsprofil
Low toxicity by ingestion and skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
läuterung methode
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.]