Caryophyllene supplier | CasNO.87-44-5

Name
BETA-CARYOPHYLLENE
EINECS 204-267-6
CAS No. 87-44-5
Article Data19
CAS DataBase
Density 0.894 g/cm³
Solubility Insoluble in water, soluble in ethanol
Melting Point <25℃
Formula C15H24
Boiling Point 268.359 °C at 760 mmHg
Molecular Weight 206.371
Flash Point 104.917 °C
Transport Information
Appearance Pale yellow oily liquid with an odor midway between odor of cloves and turpentine.
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-, (E)-(1R,9S)-(-)- (8CI);Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-;(-)-(E)-Caryophyllene;(-)-Caryophyllene;(-)-E-Caryophyllene;(-)-trans-Caryophyllene;(-)-b-Caryophyllene;(E)-Caryophyllene;Caryophyllene;Caryophyllene B;NSC 11906;l-Caryophyllene;trans-Caryophyllene;b-Caryophyllen;b-Caryophyllene;b-Caryophyllene, (-);
PSA 0.00000
LogP 4.72520

Synthetic route

: 60362-44-9
(1S,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-(5E)-en-2-one

: 1779-49-3
Methyltriphenylphosphonium bromide

: 87-44-5
β-caryophyllene

Conditions

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 23℃; Stage #2: (1S,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-(5E)-en-2-one In tetrahydrofuran; hexane at 23℃; for 1h; Further stages.;	79%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.166667h; Inert atmosphere; Stage #2: (1S,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-(5E)-en-2-one In tetrahydrofuran at -78 - 20℃; for 24h; Inert atmosphere;	48%

: (E)-caryophyll-4-en-8-yl p-nitrobenzoate

A: 87-44-5
β-caryophyllene

B: 169220-06-8
(1S,2R,5R,6S,9R)-2,6,10,10-tetramethyltricyclo<7.2.0.02,5>undecan-6-ol

C: 60269-12-7
(1S,2R,9R,E)-2,6,10,10-tetramethylbicyclo[7.2.0]undec-5-en-2-ol

Conditions

Conditions	Yield
With water In pyridine; acetone at 125℃; for 2h;	A 70% B 3% C 10%

...Expand

: 372-97-4, 13058-04-3, 25744-33-6, 27248-37-9, 27248-38-0, 40716-68-5
farnesyl pyrophosphate

A: 6753-98-6
α-caryophyllene

B: 87-44-5
β-caryophyllene

C: 68832-35-9
2-epi-trans-β-caryophyllene

D: 2-((1S,3aS,7aS,E)-1,6,6-trimethyloctahydro-4H-inden-4-ylidene)propan-1-ol

E: 104975-19-1
(+)-isoafricanol

F: african-1-ene

G: δ9,10-africanene

Conditions

Conditions	Yield
With sesquiterpene cyclase from Trichoderma spp. In aq. buffer at 28℃; for 3h; pH=8.2; Enzymatic reaction;	A n/a B n/a C n/a D 45% E n/a F n/a G n/a

...Expand

: 60269-12-7
(1S,2R,9R,E)-2,6,10,10-tetramethylbicyclo[7.2.0]undec-5-en-2-ol

A: 1176003-49-8
(-)-(1S,4S,7R,8R,9S)-9-epi-presilphiperfolan-1-ol

B: 87-44-5
β-caryophyllene

C: (2aS,2a1S,4aS,7S,7aS)-2a,4,4a,7-tetramethyl-2,2a,2a1,4a,5,6,7,7a-octahydro-1H-cyclopenta[cd]indene

D: (2aS,2a1R,5S,7aR)-1,1,2a,5-tetramethyl-2,2a,2a1,3,5,6,7,7a-octahydro-1H-cyclopenta[cd]indene

Conditions

Conditions	Yield
With hydrogenchloride; C-undecyl resorcin[4]arene In chloroform; water at 30℃; for 288h;	A n/a B n/a C n/a D 8%

...Expand

: 65563-95-3
4,5-epithiocaryophyllene

: 87-44-5
β-caryophyllene

Conditions

Conditions	Yield
With triphenylphosphine In dibutyl ether at 130℃; for 0.666667h;	99 % Chromat.

: 60594-22-1
caryophyllene oxide

A: 87-44-5
β-caryophyllene

B: 136296-35-0
(1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undeca-3-ene

C: 136296-38-3
(1R,9S)-4,8-bismethylenebicyclo<7.2.0>undecane

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; phosphoric acid; silica gel; titanium tetrachloride 1.) ether, hexane, 30 min, 2.) THF, reflux, 5 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 60594-22-1
caryophyllene oxide

A: 87-44-5
β-caryophyllene

B: 118-65-0
(-)-isocaryophyllene

C: 136296-35-0
(1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undeca-3-ene

D: 136296-38-3
(1R,9S)-4,8-bismethylenebicyclo<7.2.0>undecane

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; phosphoric acid; silica gel; titanium tetrachloride 1.) ether, hexane, 30 min, 2.) THF, reflux, 5 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 60594-22-1
caryophyllene oxide

A: 87-44-5
β-caryophyllene

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

C: 86834-01-7
4,5-dihydrocaryophyllen-4β-ol

D: 92218-81-0
1R,4S,5R,9S-4,5-dihydrocaryophyllen-5-ol

Conditions

Conditions	Yield
With ammonia; lithium In diethyl ether for 3h;	A 0.03 g B 0.75 g C 0.25 g D 1.20 g

...Expand

: 50277-33-3, 78683-81-5, 79768-25-5, 123355-03-3
14-hydroxy-4,5-dihydro-caryophyllene

A: 87-44-5
β-caryophyllene

B: (1R,2R,5S)-4,4-Dimethyltricyclo<6.3.2.02,5>tridec-8(9)-en-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; water; phosphorus tribromide 1.) Et2O, -10 deg C, 7 min; 2.) Et2O, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

flower buds of eugenia caryophyllata: flower buds of eugenia caryophyllata

: 87-44-5
β-caryophyllene

Conditions

Conditions	Yield
With steam Destillation;

: 372-97-4, 13058-04-3, 25744-33-6, 27248-37-9, 27248-38-0, 40716-68-5
farnesyl pyrophosphate

: 87-44-5
β-caryophyllene

Conditions

Conditions	Yield
With recombinant β-caryophyllene synthase from Artemisia annua; magnesium chloride; manganese(ll) chloride pH=7.0; Enzyme kinetics;

: (2E,6E)-[2-(2)H1]-farnesyl diphosphate trisammonium salt

A: (5R,8S,8aS)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,4,5,6,7,8,8a-octahydroazulene

B: 20085-93-2
(1R,3S,6S,7S,8S)-3,6,8-trimethyl-2-methylenetricyclo[5.3.1.03,8]undecane

C: 1215267-72-3
[5-(2)H1]-patchoulol

D: 1215267-73-4
[5,12-(2)H2]-patchoulol

E: 87-44-5
β-caryophyllene

F: 489-81-6, 3691-11-0, 28890-02-0, 29026-00-4, 31682-28-7
δ-guaiene

G: 514-51-2, 92841-73-1
β-patchoulene

H: 3691-12-1, 53863-54-0
(1S,4S,7R)-7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulene

I: 560-32-7
(1α,3aα,7α,8aβ)-2,3,6,7,8,8a-hexahydro-1,4,9,9-tetramethyl-1H-3a,7-methanoazulene

J: 53823-16-8
δ-patchoulene

Conditions

Conditions	Yield
With recombinant patchouli alcohol synthase; magnesium chloride at 30℃; pH=7.4; aq. buffer; Enzymatic reaction;

...Expand

: 1139-30-6
caryophyllene oxide

: 87-44-5
β-caryophyllene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol; water / 70 h / 20 °C 2.1: sodium periodate / water; methanol / 4.33 h / 20 °C / Inert atmosphere 3.1: zinc; sodium acetate; sodium iodide / dichloromethane; acetic acid / 48 h / 0 - 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - 0 °C / Inert atmosphere 4.2: 24 h / -78 - 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 4 steps
1.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol; water / 70 h / 20 °C
2.1: sodium periodate / water; methanol / 4.33 h / 20 °C / Inert atmosphere
3.1: zinc; sodium acetate; sodium iodide / dichloromethane; acetic acid / 48 h / 0 - 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - 0 °C / Inert atmosphere
4.2: 24 h / -78 - 20 °C / Inert atmosphere
View Scheme

: 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

: 87-44-5
β-caryophyllene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium periodate / water; methanol / 4.33 h / 20 °C / Inert atmosphere 2.1: zinc; sodium acetate; sodium iodide / dichloromethane; acetic acid / 48 h / 0 - 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - 0 °C / Inert atmosphere 3.2: 24 h / -78 - 20 °C / Inert atmosphere View Scheme

: 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

: 87-44-5
β-caryophyllene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: zinc; sodium acetate; sodium iodide / dichloromethane; acetic acid / 48 h / 0 - 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - 0 °C / Inert atmosphere 2.2: 24 h / -78 - 20 °C / Inert atmosphere View Scheme

: 1139-30-6
caryophyllene oxide

A: 1176003-49-8
(-)-(1S,4S,7R,8R,9S)-9-epi-presilphiperfolan-1-ol

B: 87-44-5
β-caryophyllene

C: (2aS,2a1S,4aS,7S,7aS)-2a,4,4a,7-tetramethyl-2,2a,2a1,4a,5,6,7,7a-octahydro-1H-cyclopenta[cd]indene

D: (2aS,2a1R,5S,7aR)-1,1,2a,5-tetramethyl-2,2a,2a1,3,5,6,7,7a-octahydro-1H-cyclopenta[cd]indene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ozone / dichloromethane / -78 °C 1.2: 18 h / 20 °C / Inert atmosphere 2.1: zinc; acetic acid; Cu(OAc)2·H2O / ethanol / 18 h / 20 °C / Reflux 3.1: diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 4.1: hydrogenchloride; C-undecyl resorcin[4]arene / chloroform; water / 288 h / 30 °C View Scheme

...Expand

: 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

A: 1176003-49-8
(-)-(1S,4S,7R,8R,9S)-9-epi-presilphiperfolan-1-ol

B: 87-44-5
β-caryophyllene

C: (2aS,2a1S,4aS,7S,7aS)-2a,4,4a,7-tetramethyl-2,2a,2a1,4a,5,6,7,7a-octahydro-1H-cyclopenta[cd]indene

D: (2aS,2a1R,5S,7aR)-1,1,2a,5-tetramethyl-2,2a,2a1,3,5,6,7,7a-octahydro-1H-cyclopenta[cd]indene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: zinc; acetic acid; Cu(OAc)2·H2O / ethanol / 18 h / 20 °C / Reflux 2: diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 3: hydrogenchloride; C-undecyl resorcin[4]arene / chloroform; water / 288 h / 30 °C View Scheme

...Expand

: 60362-44-9
(1S,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-(5E)-en-2-one

A: 1176003-49-8
(-)-(1S,4S,7R,8R,9S)-9-epi-presilphiperfolan-1-ol

B: 87-44-5
β-caryophyllene

C: (2aS,2a1S,4aS,7S,7aS)-2a,4,4a,7-tetramethyl-2,2a,2a1,4a,5,6,7,7a-octahydro-1H-cyclopenta[cd]indene

D: (2aS,2a1R,5S,7aR)-1,1,2a,5-tetramethyl-2,2a,2a1,3,5,6,7,7a-octahydro-1H-cyclopenta[cd]indene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 2: hydrogenchloride; C-undecyl resorcin[4]arene / chloroform; water / 288 h / 30 °C View Scheme

...Expand

: 87-44-5
β-caryophyllene

: 1671-87-0
3,6-di(2'-pyridyl)-1,2,4,5-tetrazine

: (6aR,8aS)-4a,7,7-trimethyl-9-methylene-1,4-di(pyridin-2-yl)-4a,5,6, 6a,7,8,8a,9,10,11-decahydro-2H-cyclobuta[5,6]cyclonona[1,2-d]pyridazine

Conditions

Conditions	Yield
In methanol at 20℃; for 4h;	96%

: 87-44-5
β-caryophyllene

: 150542-06-6
α,α,α-iodinefluoroacetophenone

: C23H29F2IO

Conditions

Conditions	Yield
With potassium hydrogencarbonate; phenol In 1,4-dioxane at 50℃; Inert atmosphere; Irradiation;	95%

: 87-44-5
β-caryophyllene

: α,α,α-iododifluoro-p-methylacetophenone

: 2,2-difluoro-3-((2aR,7bS)-5-iodo-2,2,4a-trimethyldecahydro-7aH-cyclobuta[e]inden-7a-yl)-1-(p-tolyl)propan- 1-one

Conditions

Conditions	Yield
With potassium hydrogencarbonate at 50℃; Inert atmosphere; Irradiation;	94%

: 87-44-5
β-caryophyllene

: 1-(4-chlorophenyl)-2,2-difluoro-2-iodoethane-1-one

: 1-(4-chlorophenyl)-2,2-difluoro-3-((2aR,7bS)-5-iodo-2,2,4a-trimethyldecahydro-7aH-cyclobuta[e]inden-7a-yl)propan-1-one

Conditions

Conditions	Yield
With potassium hydrogencarbonate In 1,4-dioxane at 50℃; Inert atmosphere; Irradiation;	93%

: 87-44-5
β-caryophyllene

: 1-(4-bromophenyl)-2,2-difluoro-2-iodoethane-1-one

: 1-(4-bromophenyl)-2,2-difluoro-3-((2aR,7bS)-5-iodo-2,2,4a-trimethyldecahydro-7aH-cyclobuta[e]inden-7a-yl)propan- 1-one

Conditions

Conditions	Yield
With potassium hydrogencarbonate at 50℃; Inert atmosphere; Irradiation;	92%

: 87-44-5
β-caryophyllene

: 118-65-0
(-)-isocaryophyllene

Conditions

Conditions	Yield
With diphenyldisulfane In toluene Irradiation;	90%
With ammonium cerium (IV) nitrate; oxygen In acetonitrile at 80℃; under 750.075 Torr; for 2h; Inert atmosphere;	85%
With selenium at 180 - 190℃; for 5h;	80%
With selenium at 185℃; for 5h;	1.44 g

: 7648-30-8
ethyl 2,2-difluoro-2-iodoacetate

: 87-44-5
β-caryophyllene

: C19H29F2IO2

Conditions

Conditions	Yield
With potassium hydrogencarbonate In 1,4-dioxane at 50℃; Inert atmosphere; Irradiation;	90%

: 87-44-5
β-caryophyllene

: 1139-30-6, 13877-94-6, 17627-43-9, 60594-22-1, 60594-23-2, 68832-36-0, 103475-43-0, 119818-36-9, 119818-37-0
Caryophyllene oxide

Conditions

Conditions	Yield
With sodium hydroxide; sodium tungstate; phenylphosphonate; dihydrogen peroxide; methyl tri-n-octyl ammonium hydrogen sulfate In water at 25℃; for 12h;	82%
With 1-methyl-pyrrolidin-2-one; 18-crown-6 ether; dihydrogen peroxide; sodium carbonate; trichlorophosphate In dichloromethane 1) -20 deg C, 1h, 2) -20 deg C, to 20 deg C;	77%
With 1-methyl-1H-imidazole; 3-Methylpyrazole; dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane at 10℃; for 1h;	> 99 %Chromat.
With sodium tungstate (VI) dihydrate; phenylphosphonate; dihydrogen peroxide; methyl tri-n-octyl ammonium hydrogen sulfate; sodium hydroxide In water at 25℃; for 12h; regioselective reaction;	82 %Chromat.

: 87-44-5
β-caryophyllene

: 92720-79-1
2,2,2-trifluoroethylsulfamate ester

: C17H28F3NO3S

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In toluene at 20℃; for 1h; Inert atmosphere;	82%

: 87-44-5
β-caryophyllene

: palladium dichloride

: di-μ-chloro(exo-η(3)-carophyllenyl)dipalladium(II)

Conditions

Conditions	Yield
With NaCl; NaOAc In acetic acid 85°C (2 h), alkene addn. (room temp.); H2O addn., extg. (CHCl3), drying (MgSO4), evapn. (reduced pressure), drying (vac.); elem. anal.;	69%

: 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.

: 87-44-5
β-caryophyllene

: 108-46-3
recorcinol

: (1R,2S,5R,8S)-4-(4,4,8-trimethyltricyclo[6.3.1.02,5]dodec-1-yl)benzene-1,3-diol

Conditions

Conditions	Yield
HB-2 zeolie In dichloromethane at 25℃; for 20h;	63%

: 87-44-5
β-caryophyllene

: norisoleptospermone

A: hyperjapone C

B: hyperjapone E

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; silver(l) oxide In diethyl ether at -78 - 20℃; for 4h; Inert atmosphere;	A 61% B n/a

...Expand

: 87-44-5
β-caryophyllene

: 3,5-dihydroxy-4,6,6-trimethyl-2-(2-methyl-1-oxopropyl)-2,4-cyclohexadiene-1-one

A: hyperjapone B

B: hyperjapone D

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; silver(l) oxide In diethyl ether at -78 - 20℃; for 17.5h; Concentration; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Overall yield = 60 %; Overall yield = 388 mg;	A 60% B n/a

...Expand

: 67-56-1
methanol

: 87-44-5
β-caryophyllene

: 101927-11-1
(1'R,4'S)-4-[4'-(4,4-dimethoxy-1-methylidenebutyl)-2',2'-dimethylcyclobutyl]butan-2-one

Conditions

Conditions	Yield
Stage #1: β-caryophyllene With ozone In methanol; ethyl acetate at -78℃; for 0.166667h; Stage #2: methanol With dimethylsulfide; montmorillonite K-10 In ethyl acetate at 20℃; for 48h;	59%

: 87-44-5
β-caryophyllene

A: 58404-89-0, 82008-48-8, 129445-45-0, 472-97-9
β-caryolanol

B: 31887-51-1
(1R,2S,7S,9R)-2,6,10,10-tetramethyltricyclo<7.2.0.02,7>undec-5-ene

C: 4545-68-0
α-neoclovene

D: 86834-01-7
4,5-dihydrocaryophyllen-4β-ol

E: 469-92-1
(-)-Clovene

F: 60269-12-7
(1S,2R,9R,E)-2,6,10,10-tetramethylbicyclo[7.2.0]undec-5-en-2-ol

Conditions

Conditions	Yield
In hexane at 68℃; for 24h;	A 57.1% B 6.2% C 9% D n/a E 15.1% F n/a

...Expand

: 87-44-5
β-caryophyllene

A: 79768-25-5
14-hydroxy-β-isocaryophyllene

B: 118-65-0
(-)-isocaryophyllene

Conditions

Conditions	Yield
With selenium(IV) oxide In ethanol at 20℃; for 3h;	A 42% B 55%
With selenium(IV) oxide In ethanol for 3h; Ambient temperature;	A 0.9 g B 1.3 g

: 50-00-0
formaldehyd

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 87-44-5
β-caryophyllene

A: (6aSR,9R,12S,15aRS)-7,8,9,10,11,12,14,15,15a,16-Decahydro-6aH,13H,17H-bicyclo<7.2.0>undecano<5',4':5,6>pyrano-<2,3-b><1>benzopyran-17-one

B: (7aSR,11S,14R,16aRS)-7,7a,8,9,11,12,13,14,15,16-Decahydro-13,13,16a-trimethyl-10-methylene-6H,10H,16aH-bicyclo<7.2.0>undecano<5',4':5,6>pyrano<3,2-c><1>benzopyran-6-one

Conditions

Conditions	Yield
In 1,4-dioxane for 3h; Heating;	A 38% B 54%

...Expand

: 87-44-5
β-caryophyllene

: 1332835-53-6
methyl 2,6-dihydroxy-4-(2-hydroxyethyl)benzoate

: 122-51-0
orthoformic acid triethyl ester

: 1332835-54-7
C26H34O5

Conditions

Conditions	Yield
With trifluoroacetic acid at 100℃;	53%

...Expand

: 87-44-5
β-caryophyllene

A: 62560-57-0
(1S,2S,5S,8S)-4,4,8-trimethyltricyclo<6.3.1.01,5>dodecan-2-ol

B: 58404-89-0, 82008-48-8, 129445-45-0, 472-97-9
β-caryolanol

C: 31887-51-1
(1R,2S,7S,9R)-2,6,10,10-tetramethyltricyclo<7.2.0.02,7>undec-5-ene

D: 4545-68-0
α-neoclovene

E: ginsenol

F: 86834-01-7
4,5-dihydrocaryophyllen-4β-ol

G: 469-92-1
(-)-Clovene

H: 131717-65-2
isocaryolan-8-ol

I: 60269-12-7
(1S,2R,9R,E)-2,6,10,10-tetramethylbicyclo[7.2.0]undec-5-en-2-ol

Conditions

Conditions	Yield
With sulfuric acid In diethyl ether at 20℃; for 72h;	A 9.4% B 48.6% C 7% D 12.7% E 6.4% F n/a G 6% H 3.9% I n/a

...Expand

: 87-44-5
β-caryophyllene

: C22H20N3O5Pol

: 1165952-91-9
cyclohexa-1,3-diene

A: 1007585-62-7
C12H13N3O2

B: 1350541-02-4
6-[hydroxy-N-(8-hydroxy-1,4,4-trimethyltricyclo[6.3.1.0(2,5)]dodec-9-yl)amino]pyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: β-caryophyllene; C22H20N3O5Pol; cyclohexa-1,3-diene In dichloromethane at 21℃; for 2h; solid phase reaction; Stage #2: With trifluoroacetic acid In dichloromethane at 21℃; solid phase reaction;	A n/a B 46%

...Expand

: 87-44-5
β-caryophyllene

: 536-74-3
phenylacetylene

: (1R,4S,7R,11S)-4,13,13-trimethyl-10-methylene-6-phenyltricyclo[9.2.0.04,7]tridec-5-ene

Conditions

Conditions	Yield
With (acetonitrile)[(2',4',6'-triisopropyl-1,1'-biphenyl-2-yl)di-tert-butylphosphine]gold(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate In dichloromethane at 23℃; for 36h; regioselective reaction;	46%

: 87-44-5
β-caryophyllene

: 158611-70-2
(4-trifluoromethyl)phenyl nitrile oxide

A: (1S,5E,9R)-6,10,10-trimethyl-4’-[4-(trifluoromethyl)phenyl]-3’H-spiro[bicyclo[7.2.0]undecane-2,2’-[1,5]oxazole]-5-ene

B: (1’S,4’R,7’S,11’R)-1’,5’,5’-trimethyl-4-12’-bis[4-(trifluoromethyl)phenyl]-3H-14’-oxa-13’-azaspiro[1,5-oxazole-2,8-tricyclo[9.3.0.04,7]tetradecan]-12’-ene

Conditions

Conditions	Yield
In dichloromethane at 20℃;	A 45% B 30%

...Expand

: 87-44-5
β-caryophyllene

A: 62560-57-0
(1S,2S,5S,8S)-4,4,8-trimethyltricyclo<6.3.1.01,5>dodecan-2-ol

B: 58404-89-0, 82008-48-8, 129445-45-0, 472-97-9
β-caryolanol

C: 31887-51-1
(1R,2S,7S,9R)-2,6,10,10-tetramethyltricyclo<7.2.0.02,7>undec-5-ene

D: 4545-68-0
α-neoclovene

E: ginsenol

F: isocaryophyllene

G: 86834-01-7
4,5-dihydrocaryophyllen-4β-ol

H: 469-92-1
(-)-Clovene

I: 131717-65-2
isocaryolan-8-ol

J: 136296-35-0
(1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undeca-3-ene

K: 136296-37-2
(1R,3Z,7Z,9S)-4,8,11,11-tetramethylbicyclo<7.2.0>undeca-3,7-diene

L: 136376-06-2
(1S,2S,5R)-1,4,4-trimethyltricyclo<6.3.1.02,5>dodec-8-ene

M: (1S,2R,5Z,9R)-2,6,10,10-tetramethyltricyclo<7.2.0.02,5>undec-5-ene

N: 169220-03-5
(1R,2S,5R,9S)-1,4,4-trimethyl-8-methylenetricyclo<7.2.0.02,5>undecane

O: 60269-12-7
(1S,2R,9R,E)-2,6,10,10-tetramethylbicyclo[7.2.0]undec-5-en-2-ol

Conditions

Conditions	Yield
With sulfuric acid In diethyl ether at 20℃; for 0.5h;	A 9.1% B 44.7% C 1% D 2.5% E 3.9% F n/a G n/a H 8.1% I 4% J n/a K n/a L 3.7% M n/a N n/a O n/a

...Expand

: 87-44-5
β-caryophyllene

A: 62560-57-0
(1S,2S,5S,8S)-4,4,8-trimethyltricyclo<6.3.1.01,5>dodecan-2-ol

B: 58404-89-0, 82008-48-8, 129445-45-0, 472-97-9
β-caryolanol

C: isocaryophyllene

D: 469-92-1
(-)-Clovene

E: 131717-65-2
isocaryolan-8-ol

F: 136296-35-0
(1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undeca-3-ene

G: 136296-37-2
(1R,3Z,7Z,9S)-4,8,11,11-tetramethylbicyclo<7.2.0>undeca-3,7-diene

H: 136376-06-2
(1S,2S,5R)-1,4,4-trimethyltricyclo<6.3.1.02,5>dodec-8-ene

I: (1S,2R,5Z,9R)-2,6,10,10-tetramethyltricyclo<7.2.0.02,5>undec-5-ene

J: 169220-03-5
(1R,2S,5R,9S)-1,4,4-trimethyl-8-methylenetricyclo<7.2.0.02,5>undecane

Conditions

Conditions	Yield
In hexane at 20℃; for 72h;	A 4.6% B 43.9% C n/a D 8.4% E 5.4% F n/a G n/a H 5.1% I n/a J n/a

...Expand

: 87-44-5
β-caryophyllene

A: 62560-57-0
(1S,2S,5S,8S)-4,4,8-trimethyltricyclo<6.3.1.01,5>dodecan-2-ol

B: 58404-89-0, 82008-48-8, 129445-45-0, 472-97-9
β-caryolanol

C: 31887-51-1
(1R,2S,7S,9R)-2,6,10,10-tetramethyltricyclo<7.2.0.02,7>undec-5-ene

D: 4545-68-0
α-neoclovene

E: ginsenol

F: isocaryophyllene

G: 86834-01-7
4,5-dihydrocaryophyllen-4β-ol

H: 469-92-1
(-)-Clovene

I: 131717-65-2
isocaryolan-8-ol

J: 136296-35-0
(1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undeca-3-ene

K: 136296-37-2
(1R,3Z,7Z,9S)-4,8,11,11-tetramethylbicyclo<7.2.0>undeca-3,7-diene

L: 60269-12-7
(1S,2R,9R,E)-2,6,10,10-tetramethylbicyclo[7.2.0]undec-5-en-2-ol

Conditions

Conditions	Yield
With sulfuric acid In acetone at 56℃; for 3h;	A 16.7% B 43.5% C 6.2% D 6.4% E 6% F n/a G n/a H 2.9% I 5.7% J n/a K n/a L n/a

...Expand

: 87-44-5
β-caryophyllene

A: 62560-57-0
(1S,2S,5S,8S)-4,4,8-trimethyltricyclo<6.3.1.01,5>dodecan-2-ol

B: 58404-89-0, 82008-48-8, 129445-45-0, 472-97-9
β-caryolanol

C: 31887-51-1
(1R,2S,7S,9R)-2,6,10,10-tetramethyltricyclo<7.2.0.02,7>undec-5-ene

D: (1R,2R,6S,7S)-2,6,8,8-tetramethyltricyclo[5.2.2.01,6]undecane

E: ginsenol

F: 123414-62-0
3,4,8α-trimethyl-1α-(12-methylene)tricyclo<6.3.1.01,5>dodeca-3,5-diene

G: 86834-01-7
4,5-dihydrocaryophyllen-4β-ol

H: 469-92-1
(-)-Clovene

I: 60269-12-7
(1S,2R,9R,E)-2,6,10,10-tetramethylbicyclo[7.2.0]undec-5-en-2-ol

Conditions

Conditions	Yield
In hexane at 20℃; for 0.0833333h;	A 1.3% B 43.5% C 2.1% D 1.5% E 0.8% F 8% G n/a H 8.5% I n/a

...Expand

Caryophyllene Consensus Reports

Reported in EPA TSCA Inventory.

Caryophyllene Specification

The Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-, with the CAS registry number 87-44-5, is also known as (-)-trans-Caryophyllene. It belongs to the product categories of Sesqui-Terpenoids; Biochemistry; Terpenes; Terpenes (Others). Its EINECS number is 201-746-1. This chemical's molecular formula is C₁₅H₂₄ and molecular weight is 204.35. What's more, its systematic name is (1R,4E,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene. Its classification codes are: (1)Natural Product; (2)Skin / Eye Irritant. This chemical should be sealed in a brown glass bottle and stored in a cool place. It is one of the chemical compounds that contributes to the spiciness of black pepper. It may have antiinflammatory action. It can be prepared by separating the clove leaf oil , clove stem oil and cinnamon leaf oil. This substance is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems. It is usually found as a mixture with isocaryophyllene and α-humulene, a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, a rarity in nature.

Physical properties of Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- are: (1)ACD/LogP: 6.416; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.42; (4)ACD/LogD (pH 7.4): 6.42; (5)ACD/BCF (pH 5.5): 44308.57; (6)ACD/BCF (pH 7.4): 44308.57; (7)ACD/KOC (pH 5.5): 73712.05; (8)ACD/KOC (pH 7.4): 73712.05; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.495; (13)Molar Refractivity: 66.596 cm³; (14)Molar Volume: 228.452 cm³; (15)Polarizability: 26.401×10^-24cm³; (16)Surface Tension: 29.7040004730225 dyne/cm; (17)Density: 0.894 g/cm³; (18)Flash Point: 104.917 °C; (19)Enthalpy of Vaporization: 48.603 kJ/mol; (20)Boiling Point: 268.359 °C at 760 mmHg; (21)Vapour Pressure: 0.0130000002682209 mmHg at 25°C.

Uses of Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-: it can be used to produce Caryophyllenoxid at the temperature of -20 °C. It will need reagents 30% H₂O₂, N-methylpyrrolidone/POCl₃, Na₂CO₃, 18-crown-6and solvent CH₂Cl₂ with the reaction time of 1 hour. The yield is about 77%.

Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- can be used to produce Caryophyllenoxid at the temperature of -20 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: C1(=C)\CC/C=C(/CC[C@@H]2[C@@H]1CC2(C)C)C
(2)Std. InChI: InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1
(3)Std. InChIKey: NPNUFJAVOOONJE-GFUGXAQUSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD	intratracheal	> 48mg/kg (48mg/kg)	LUNGS, THORAX, OR RESPIRATION: PULMONARY EMBOLI	Archives of Toxicology. Vol. 59, Pg. 78, 1986.

Product Name

BETA-CARYOPHYLLENE

Synthetic route

Caryophyllene Consensus Reports

Caryophyllene Specification

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