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Name	b-Caryophyllene oxide	EINECS	214-519-7
CAS No.	1139-30-6	Density	0.985 g/cm³
PSA	12.53000	LogP	3.93640
Solubility	N/A	Melting Point	62-63 °C(lit.)
Formula	C₁₅H₂₄O	Boiling Point	279.682 °C at 760 mmHg
Molecular Weight	220.355	Flash Point	119.667 °C
Transport Information	N/A	Appearance	white crystalline powder
Safety	26	Risk Codes	36/38
Molecular Structure		Hazard Symbols	Xi
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;	Article Data	29

b-Caryophyllene oxide 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

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%

: 87-44-5
β-caryophyllene

: 1139-30-6
caryophyllene oxide

Conditions

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.

: 93-59-4
Perbenzoic acid

: 87-44-5
β-caryophyllene

: 1139-30-6
caryophyllene oxide

Conditions

Conditions	Yield
With chloroform

: 2311-91-3
monoperoxyphthalic acid

: 87-44-5
β-caryophyllene

: 1139-30-6
caryophyllene oxide

Conditions

Conditions	Yield
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

Conditions	Yield
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

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;

: 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

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.

: 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

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

: 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

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%

: 1139-30-6
caryophyllene oxide

: (-)-humulene epoxide II

Conditions

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

b-Caryophyllene oxide Chemical Properties

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

b-Caryophyllene oxide 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.

b-Caryophyllene oxide Consensus Reports

Reported in EPA TSCA Inventory.

b-Caryophyllene oxide 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

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