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Caryophyllene

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Name

Caryophyllene

EINECS 204-267-6
CAS No. 87-44-5 Density 0.894 g/cm3
PSA 0.00000 LogP 4.72520
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 N/A 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 Molecular Structure of 87-44-5 (BETA-CARYOPHYLLENE) Hazard Symbols N/A
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, (-);

Article Data 19

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

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
ConditionsYield
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
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
ConditionsYield
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%
65563-95-3

4,5-epithiocaryophyllene

87-44-5

β-caryophyllene

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

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.

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