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CAS No.: | 1139-30-6 |
---|---|
Name: | CARYOPHYLLENE OXIDE |
Article Data: | 29 |
Molecular Structure: | |
Formula: | C15H24O |
Molecular Weight: | 220.355 |
Synonyms: | Caryophyllene 4b,5a-oxide;trans-Caryophylleneoxide;b-Caryophyllene epoxide;6,7-Epoxy-3(15)-caryophyllene;(-)-Epoxydihydrocaryophyllene;(-)-b-Caryophyllene epoxide;(-)-b-Caryophyllene oxide;4b,5a-Epoxycaryophyllene;5-Oxatricyclo[8.2.0.04,6]dodecane,4,12,12-trimethyl-9-methylene-, [1R-(1R*,4R*,6R*,10S*)]-;Caryophyllene oxide(6CI);Caryophyllene, epoxide (7CI);(-)-Caryophyllene oxide;Caryophyllene 4b,5a-epoxide; |
EINECS: | 214-519-7 |
Density: | 0.985 g/cm3 |
Melting Point: | 62-63 °C(lit.) |
Boiling Point: | 279.682 °C at 760 mmHg |
Flash Point: | 119.667 °C |
Appearance: | white crystalline powder |
Hazard Symbols: | Xi |
Risk Codes: | 36/38 |
Safety: | 26 |
PSA: | 12.53000 |
LogP: | 3.93640 |
Methyltriphenylphosphonium bromide
(1R,4R,6R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodcan-9-one
caryophyllene oxide
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.166667h; Stage #2: (1R,4R,6R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodcan-9-one In tetrahydrofuran at -78 - 20℃; for 24h; | 74% |
Conditions | Yield |
---|---|
With 4-methyloxetan-2-one; CpLIP2 Y179F (ipase/acyltransferase) from Candida parapsilosis; dihydrogen peroxide In aq. phosphate buffer; water at 20℃; for 24h; pH=6.5; Reagent/catalyst; Enzymatic reaction; | 67% |
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h; | 66% |
With peracetic acid; sodium acetate In dichloromethane | |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 0.5h; | 75 % Chromat. |
Conditions | Yield |
---|---|
With chloroform |
Conditions | Yield |
---|---|
With diethyl ether |
β-caryophyllene
A
(1R,4R,5R,9S,11R)-4,5-epoxy-12-nor-8(14)-caryophyllene-11-ol
B
(1R,4R,5R,9S,11R)-4,5-epoxy-caryophyll-8(14)-en-12-oic acid
C
15-hydroxycaryophyllene oxide
D
caryophyllene oxide
Conditions | Yield |
---|---|
for 72h; Diplodia gossypina ATCC 10936; Further byproducts given; | A 220 mg B 900 mg C 300 mg D 65 mg |
β-caryophyllene
A
caryophyllene oxide
B
(5S,6S)-5,6-epoxy-5,6-dihydrocaryophyllene
Conditions | Yield |
---|---|
With peracetic acid; sodium acetate In dichloromethane at 0℃; Yield given. Yields of byproduct given; | |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2h; Title compound not separated from byproducts; | A 81 % Spectr. B 19 % Spectr. |
With peracetic acid; sodium acetate In dichloromethane at 0℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
β-caryophyllene
A
caryophyllene oxide
B
(2R,5R,6R)-2,12:5,6-diepoxycaryophyllane
C
(1R,4R,6R,9S,10S)-4,12,12-trimethylspiro(5-oxatricyclo[8.2.0.04,6]dodecane-9,2'-oxirane)
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 0.5h; Product distribution; effect of stoichiometry, temperature, reaction time; | A 52 % Chromat. B 21 % Chromat. C 21 % Chromat. |
5,6-epoxy-2-hydroxymethyl-6,10,10-trimethyl-bicyclo[7.2.0]undecan-2-ol
caryophyllene oxide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium periodate / water; methanol / 4.33 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - 0 °C 2.2: 24 h / -78 - 20 °C View Scheme |
caryophyllene oxide
1,5,5,8-tetramethyl-[1R-(1R*,3E,7E,11R*)]-12-oxabicyclo[9.1.0]dodeca-3,7-diene
Conditions | Yield |
---|---|
With phenylsilane In benzene for 2h; | 100% |
With (+/-)-trans-Co(III)-salen-Cl; phenylsilane In benzene for 2h; | 100% |
With C32H46ClCoN2O2; phenylsilane In benzene at 22℃; for 5h; Inert atmosphere; | 95% |
caryophyllene oxide
Conditions | Yield |
---|---|
With (+/-)-trans-Co(III)-salen-Cl; phenylsilane In benzene for 2h; | 100% |
IUPAC Name: (-)-beta-Caryophyllene epoxide
The MF of (-)-beta-Caryophyllene epoxide (1139-30-6) is C15H24O.
The MW of (-)-beta-Caryophyllene epoxide (1139-30-6) is 220.35.
Synonyms of (-)-beta-Caryophyllene epoxide (1139-30-6): (-)-b-Caryophyllene epoxide ; (-)-beta-Caryophyllene epoxide ; (-)-Epoxydihydrocaryophyllene ; (1R,4R,6R,10S)-4,12,12-Trimethyl-9-methylen-5-oxatricyclo[8.2.0.0~4,6~]dodecan ; 5-Oxatricyclo(8.2.0.0(4,6))dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)-
Product Categories: Alphabetical Listings;C-D;Flavors and Fragrances
Form: white crystalline powder
Index of Refraction: 1.507
Storage temp: 2-8 °C
EINECS: 214-519-7
Density: 0.98 g/ml
Flash Point: 119.7 °C
Boiling Point: 279.7 °C
Melting Point: 62-63 °C
FEMA: 4085
1. | skn-rbt 500 mg/24H MOD | FCTOD7 Food and Chemical Toxicology. 21 (1983),661. | ||
2. | orl-rat LD50:>5 g/kg | FCTOD7 Food and Chemical Toxicology. 21 (1983),661. | ||
3. | skn-rbt LD50:>2 g/kg | FCTOD7 Food and Chemical Toxicology. 21 (1983),661. |
Reported in EPA TSCA Inventory.
Low toxicity by ingestion and skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.Safety information of (-)-beta-Caryophyllene epoxide (1139-30-6):
Hazard Codes Xi
Risk Statements
36/38 Irritating to eyes and skin
Safety Statements
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany 2
RTECS RP5530000
F 1-10