Basic Information | Post buying leads | Suppliers | Cas Database |
(1S,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-(5E)-en-2-one
Methyltriphenylphosphonium bromide
β-caryophyllene
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% |
A
β-caryophyllene
B
(1S,2R,5R,6S,9R)-2,6,10,10-tetramethyltricyclo<7.2.0.02,5>undecan-6-ol
C
(1S,2R,9R,E)-2,6,10,10-tetramethylbicyclo[7.2.0]undec-5-en-2-ol
Conditions | Yield |
---|---|
With water In pyridine; acetone at 125℃; for 2h; | A 70% B 3% C 10% |
farnesyl pyrophosphate
A
α-caryophyllene
B
β-caryophyllene
C
2-epi-trans-β-caryophyllene
E
(+)-isoafricanol
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 |
(1S,2R,9R,E)-2,6,10,10-tetramethylbicyclo[7.2.0]undec-5-en-2-ol
A
(-)-(1S,4S,7R,8R,9S)-9-epi-presilphiperfolan-1-ol
B
β-caryophyllene
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% |
4,5-epithiocaryophyllene
β-caryophyllene
Conditions | Yield |
---|---|
With triphenylphosphine In dibutyl ether at 130℃; for 0.666667h; | 99 % Chromat. |
caryophyllene oxide
A
β-caryophyllene
B
(1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undeca-3-ene
C
(1R,9S)-4,8-bismethylenebicyclo<7.2.0>undecane
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; |
caryophyllene oxide
A
β-caryophyllene
B
(-)-isocaryophyllene
C
(1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undeca-3-ene
D
(1R,9S)-4,8-bismethylenebicyclo<7.2.0>undecane
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; |
caryophyllene oxide
A
β-caryophyllene
B
(1S,2S,5R,8R,9R)-1,4,4,8-tetramethyltricyclo[6.3.0.02,5]undecan-9-ol
C
4,5-dihydrocaryophyllen-4β-ol
D
1R,4S,5R,9S-4,5-dihydrocaryophyllen-5-ol
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 |
14-hydroxy-4,5-dihydro-caryophyllene
A
β-caryophyllene
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; |
β-caryophyllene
Conditions | Yield |
---|---|
With steam Destillation; |
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%.
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. |