b-Caryophyllene oxide supplier

Name
CARYOPHYLLENE OXIDE
EINECS 214-519-7
CAS No. 1139-30-6
Article Data29
CAS DataBase
Density 0.985 g/cm³
Solubility
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
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;
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

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

...Expand

: 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.

...Expand

: 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%

: 1139-30-6
caryophyllene oxide

: 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

Conditions

Conditions	Yield
Stage #1: caryophyllene oxide With ozone In dichloromethane at -78℃; Stage #2: With acetic acid; zinc In dichloromethane; water at 20℃; for 18h; Inert atmosphere;	98%
With ruthenium trichloride; sodium periodate In water; ethyl acetate; acetonitrile for 6h;	61%
With ruthenium trichloride; sodium periodate; water In ethyl acetate; acetonitrile for 6h;	61%

: 1361382-43-5
6-(trimethylsilyl)hex-5-yn-1-yl 2-cyano-2-diazoacetate

: 1139-30-6
caryophyllene oxide

: C27H41NO3Si

Conditions

Conditions	Yield
With Rh2(esp)2 In dichloromethane at 22℃; for 4h; Inert atmosphere; diastereoselective reaction;	94%

: 1139-30-6
caryophyllene oxide

: 19431-79-9
1R,5S,9S-11,11-dimethyl-4,8-bismethylenebicyclo<7.2.0>undecan-5-ol

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane Heating;	90%
With n-butyllithium In diethyl ether
With ethenetetracarbonitrile; lithium bromide In acetone
With ethenetetracarbonitrile; lithium bromide In acetone

: 1139-30-6
caryophyllene oxide

: ((1R,4R,6R,9S,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methanol

Conditions

Conditions	Yield
Stage #1: caryophyllene oxide With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran for 8h; Inert atmosphere; Cooling with ice; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 20℃; for 2h;	90%

: 1139-30-6
caryophyllene oxide

: 507-09-5
thioacetic acid

: ({(1R,4R,6R,9R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodec-9-yl}methyl)ethanethioate

Conditions

Conditions	Yield
With silica gel regioselective reaction;	89%

: 1139-30-6
caryophyllene oxide

: 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

Conditions

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; tert-butyl alcohol at 20℃; for 70h;	82%

: 3034-53-5
2-bromo-1,3-thiazole

: 1139-30-6
caryophyllene oxide

: 2-(((1S,11S,Z)-7,7,11-trimethyl-12-oxabicyclo[9.1.0]dodec-4-en-4-yl)methyl)thiazole

Conditions

Conditions	Yield
With formic acid; tributyl-amine; tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile at 45℃; for 19h; Inert atmosphere; Irradiation; Sealed tube; diastereoselective reaction;	71%

: 1139-30-6
caryophyllene oxide

A: 122621-21-0
(1R,2S,5R,8S,9R)-1,4,4,8-tetramethyltricyclo[6.3.0.02,5]undecan-9-ol

B: 122571-86-2
(1S,2S,5R,8R,9R)-1,4,4,8-tetramethyltricyclo[6.3.0.02,5]undecan-9-ol

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; manganese; chloro-trimethyl-silane; bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 20℃; for 0.666667h;	A 65% B 30%

: 1139-30-6
caryophyllene oxide

: 75-66-1
2-methylpropan-2-thiol

A: 2649-64-1
clovanediol

B: (1S,2S,5S,8R,9R)-2-tert-butylsulfanyl-4,4,8-trimethyltricyclo[6.3.1.01,5]dodecan-9-ol

C: 475285-25-7
4,10,10-trimethyl-7-methylene-1β,8α-bicyclo[6.2.0]decene-4-carboxaldehyde

Conditions

Conditions	Yield
With zinc(II) chloride In dichloromethane Reflux;	A 6% B 63% C 7%

...Expand

: 624-76-0
Iodoethanol

: 1139-30-6
caryophyllene oxide

: 1112901-60-6
2β-(2-iodoethoxy)clovan-9α-ol

Conditions

Conditions	Yield
With ethenetetracarbonitrile at 25℃;	62%

: 1139-30-6
caryophyllene oxide

: 103189-78-2
4,9,12,12-tetramethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-ol

Conditions

Conditions	Yield
With iron(III)-acetylacetonate; methyl 4-nitrobenzenesulfonate; phenylsilane; sodium hydrogencarbonate In methanol at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere; diastereoselective reaction;	62%

: 1139-30-6
caryophyllene oxide

: 92760-17-3
(1R,5S,8R,9R)-4,4,8-trimethylbicyclo<6.3.1.01,5>dodeca-2-en-9-ol

Conditions

Conditions	Yield
With bithmuth(III) triflate hydrate In dichloromethane for 0.166667h; Wagner-Meerwein rearrangement; Reflux;	60%
With methanol; fluorosulfonylchloride; fluorosulphonic acid 1.) -100 deg C, 2.) diethyl ether; Yield given. Multistep reaction;

: 1139-30-6
caryophyllene oxide

: 100-53-8
phenylmethanethiol

A: (1S,2S,6S,9R)-2-(benzylsulfanyl)-6,2,10,10-tetramethylbicyclo[7.2.0]undecan-5-one

B: (1S,2S,5S,8R)-2-(benzylsulfanyl)-4,4,8-trimethyltricyclo[6.3.1.01,5]dodec-9-ene

C: (1S,2S,5S,8R,9R)-2,9-bis(benzylsulfanyl)-4,4,8-trimethyltricyclo[6.3.1.01,5]dodecane

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In chloroform for 5h; Reflux;	A 21% B 25% C 51%

...Expand

: 1139-30-6
caryophyllene oxide

: 75-66-1
2-methylpropan-2-thiol

A: 19431-76-6
caryophylla-2(12),6(13)-dien-5β-ol

B: 2649-64-1
clovanediol

C: (1S,2S,5S,8R)-2-tert-butylsulfanyl-4,4,8-trimethyltricyclo[6.3.1.01,5]dodec-9-ene

D: (1S,2S,5S,8R,9R)-2,9-bistert-butylsulfanyl-4,4,8-trimethyltricyclo[6.3.1.01,5]dodecane

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane Reflux;	A 10% B 7% C 35% D 48%

...Expand

: 1139-30-6
caryophyllene oxide

: 62-53-3
aniline

: 75-05-8
acetonitrile

A: 2β-phenylaminoclovan-9α-ol

B: N-(9α-hydroxyclovan-2β-yl)-N'-phenyl acetamidine

Conditions

Conditions	Yield
With tin(II) trifluoromethanesulfonate at 80℃; for 24h;	A 5% B 47%

...Expand

: 1139-30-6
caryophyllene oxide

A: 19431-76-6
caryophylla-2(12),6(13)-dien-5β-ol

B: 19431-79-9
1R,5S,9S-11,11-dimethyl-4,8-bismethylenebicyclo<7.2.0>undecan-5-ol

C: isocaryolan-9-one

Conditions

Conditions	Yield
With ethenetetracarbonitrile In dimethyl sulfoxide for 96h; Ambient temperature;	A 46% B 19% C 2%

...Expand

: 1139-30-6
caryophyllene oxide

: 100-53-8
phenylmethanethiol

A: (1S,2S,5S,8R,9R)-2-(benzylsulfanyl)-4,4,8-trimethyltricyclo[6.3.1.01,5]dodecan-9-ol

B: (1S,2S,6S,9R)-2-(benzylsulfanyl)-6,2,10,10-tetramethylbicyclo[7.2.0]undecan-5-one

C: (1S,2S,5R,9S)-7-(benzylsulfanyl)-1,4,4,8-tetramethyl-12-oxatricyclo[7.2.1.02,5]dodecane

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In chloroform at 20℃; for 2h;	A 46% B 13% C 26%

...Expand

: 1139-30-6
caryophyllene oxide

: (+)-(6R,7R)-6,7-epoxy-6,7-dihydro-β-farnesene

Conditions

Conditions	Yield
at 550℃; under 0.5 Torr;	45%
at 550℃; under 0.1 - 2 Torr; for 0.000277778h; Product distribution; Thermodynamic data; flash vacuum thermolysis; further stereoisomers; variation of temperature; activation energy;	43%

: 1139-30-6
caryophyllene oxide

: 100-53-8
phenylmethanethiol

A: 68263-68-3
4α,11,11-trimethyl-8-methylene-1β,9α-bicyclo[7.2.0]undecan-5-one

B: 2649-64-1
clovanediol

C: C15H24O

D: (1S,2S,5S,8R,9R)-2-(benzylsulfanyl)-4,4,8-trimethyltricyclo[6.3.1.01,5]dodecan-9-ol

Conditions

Conditions	Yield
With zinc(II) chloride In chloroform for 5h; Reflux;	A 12% B 26% C 10% D 45%

...Expand

: 1139-30-6
caryophyllene oxide

: 75-66-1
2-methylpropan-2-thiol

A: 68263-68-3
4α,11,11-trimethyl-8-methylene-1β,9α-bicyclo[7.2.0]undecan-5-one

B: 2649-64-1
clovanediol

C: (1S,2S,5S,8R,9R)-2-tert-butylsulfanyl-4,4,8-trimethyltricyclo[6.3.1.01,5]dodecan-9-ol

D: 475285-25-7
4,10,10-trimethyl-7-methylene-1β,8α-bicyclo[6.2.0]decene-4-carboxaldehyde

Conditions

Conditions	Yield
With zinc(II) chloride In dichloromethane at 20℃; Catalytic behavior;	A 8% B 21% C 44% D 7%

...Expand

: 1139-30-6
caryophyllene oxide

: 540-51-2
2-bromoethanol

: 357186-68-6
2β-(2-bromoethoxy)clovan-9α-ol

Conditions

Conditions	Yield
With ethenetetracarbonitrile at 25℃;	43%

: 67-56-1
methanol

: 1139-30-6
caryophyllene oxide

A: 19431-76-6
caryophylla-2(12),6(13)-dien-5β-ol

B: 127156-29-0
9α-hydroxy-2β-methoxyclovane

C: isocaryolan-9-one

D: (1S,5R,6R,9R)-6-Methoxy-10,10-dimethyl-2-methylene-bicyclo[7.2.0]undecan-5-ol

Conditions

Conditions	Yield
With ethenetetracarbonitrile for 24h; Ambient temperature; Further byproducts given;	A 20% B 42% C 11% D 6%

...Expand

: 67-56-1
methanol

: 1139-30-6
caryophyllene oxide

A: 19431-76-6
caryophylla-2(12),6(13)-dien-5β-ol

B: 127156-29-0
9α-hydroxy-2β-methoxyclovane

C: (Z)-(1R,5R,8R,9S)-8-Methoxy-4,8,11,11-tetramethyl-bicyclo[7.2.0]undec-3-en-5-ol

D: (1S,5R,6R,9R)-6-Methoxy-10,10-dimethyl-2-methylene-bicyclo[7.2.0]undecan-5-ol

Conditions

Conditions	Yield
With ethenetetracarbonitrile for 24h; Ambient temperature; Further byproducts given;	A 20% B 42% C 3% D 6%

...Expand

: 1139-30-6
caryophyllene oxide

A: 19431-76-6
caryophylla-2(12),6(13)-dien-5β-ol

B: 127156-29-0
9α-hydroxy-2β-methoxyclovane

C: isocaryolan-9-one

D: (1S,5R,6R,9R)-6-Methoxy-10,10-dimethyl-2-methylene-bicyclo[7.2.0]undecan-5-ol

Conditions

Conditions	Yield
With ethenetetracarbonitrile In methanol for 24h; Ambient temperature; Further byproducts given;	A 20% B 42% C 11% D 6%

...Expand

: 1139-30-6
caryophyllene oxide

: 104-94-9
4-methoxy-aniline

: 75-05-8
acetonitrile

A: 2β-(p-methoxyphenylamino)clovan-9α-ol

B: N-((3S,3aS,6R,7R,9aS)-6-Hydroxy-1,1,7-trimethyl-decahydro-3a,7-methano-cyclopentacycloocten-3-yl)-N'-(4-methoxy-phenyl)-acetamidine

Conditions

Conditions	Yield
With tin(II) trifluoromethanesulfonate at 80℃; for 24h;	A 2% B 42%

...Expand

: 1139-30-6
caryophyllene oxide

: 75-05-8
acetonitrile

: 106-40-1
4-bromo-aniline

: N-(4-Bromo-phenyl)-N'-((3S,3aS,6R,7R,9aS)-6-hydroxy-1,1,7-trimethyl-decahydro-3a,7-methano-cyclopentacycloocten-3-yl)-acetamidine

Conditions

Conditions	Yield
With tin(II) trifluoromethanesulfonate at 80℃; for 24h;	39%

...Expand

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

Product Name

CARYOPHYLLENE OXIDE

Synthetic route

b-Caryophyllene oxide Chemical Properties

b-Caryophyllene oxide Toxicity Data With Reference

b-Caryophyllene oxide Consensus Reports

b-Caryophyllene oxide Safety Profile

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