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1139-30-6

Basic Information
CAS No.: 1139-30-6
Name: CARYOPHYLLENE OXIDE
Article Data: 29
Molecular Structure:
Molecular Structure of 1139-30-6 (CARYOPHYLLENE OXIDE)
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: IrritantXi
Risk Codes: 36/38
Safety: 26
PSA: 12.53000
LogP: 3.93640
Synthetic route
1779-49-3

Methyltriphenylphosphonium bromide

10306-22-6, 10306-31-7, 24173-71-5, 34175-71-8

(1R,4R,6R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodcan-9-one

1139-30-6

caryophyllene oxide

Conditions
ConditionsYield
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%
87-44-5

β-caryophyllene

1139-30-6

caryophyllene oxide

Conditions
ConditionsYield
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.
93-59-4

Perbenzoic acid

87-44-5

β-caryophyllene

1139-30-6

caryophyllene oxide

Conditions
ConditionsYield
With chloroform
2311-91-3

monoperoxyphthalic acid

87-44-5

β-caryophyllene

1139-30-6

caryophyllene oxide

Conditions
ConditionsYield
With diethyl ether
87-44-5

β-caryophyllene

A

118122-82-0

(1R,4R,5R,9S,11R)-4,5-epoxy-12-nor-8(14)-caryophyllene-11-ol

B

108525-13-9

(1R,4R,5R,9S,11R)-4,5-epoxy-caryophyll-8(14)-en-12-oic acid

C

73510-14-2

15-hydroxycaryophyllene oxide

D

1139-30-6

caryophyllene oxide

Conditions
ConditionsYield
for 72h; Diplodia gossypina ATCC 10936; Further byproducts given;A 220 mg
B 900 mg
C 300 mg
D 65 mg
87-44-5

β-caryophyllene

A

1139-30-6

caryophyllene oxide

B

103475-43-0

(5S,6S)-5,6-epoxy-5,6-dihydrocaryophyllene

Conditions
ConditionsYield
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;
87-44-5

β-caryophyllene

A

1139-30-6

caryophyllene oxide

B

60444-80-6

(2R,5R,6R)-2,12:5,6-diepoxycaryophyllane

C

60479-10-9

(1R,4R,6R,9S,10S)-4,12,12-trimethylspiro(5-oxatricyclo[8.2.0.04,6]dodecane-9,2'-oxirane)

Conditions
ConditionsYield
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.
10577-25-0, 60479-11-0, 60479-16-5, 60479-18-7, 123808-25-3

5,6-epoxy-2-hydroxymethyl-6,10,10-trimethyl-bicyclo[7.2.0]undecan-2-ol

1139-30-6

caryophyllene oxide

Conditions
ConditionsYield
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
1139-30-6

caryophyllene oxide

19888-34-7, 67737-67-1, 90820-79-4, 108101-44-6

1,5,5,8-tetramethyl-[1R-(1R*,3E,7E,11R*)]-12-oxabicyclo[9.1.0]dodeca-3,7-diene

Conditions
ConditionsYield
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%
1139-30-6

caryophyllene oxide

(-)-humulene epoxide II

Conditions
ConditionsYield
With (+/-)-trans-Co(III)-salen-Cl; phenylsilane In benzene for 2h;100%
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Chemistry

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

Toxicity Data With Reference

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.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

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