Caryophyllene epoxide

Base Information

• Chemical Name: Caryophyllene epoxide
• CAS No.: 1139-30-6
• Molecular Formula: C15H24O
• Molecular Weight: 220.355
• Hs Code.: 29109000
• European Community (EC) Number: 237-642-8,241-609-3
• DSSTox Substance ID: DTXSID50859585
• Nikkaji Number: J280.354B
• Wikidata: Q67879768
• Metabolomics Workbench ID: 47505
• Mol file: 1139-30-6.mol

Synonyms:4,12,12-trimethyl-9-methylene-5-oxatricyclo(8.2.0.04,6)dodecane;beta-caryophyllene epoxide;beta-caryophyllene oxide;caryophyllene oxide

Chemical Property of Caryophyllene epoxide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00672mmHg at 25°C
• Melting Point: 62-63 °C(lit.)
• Refractive Index: 1.4956
• Boiling Point: 279.682 °C at 760 mmHg
• Flash Point: 119.667 °C
• PSA: 12.53000
• Density: 0.985 g/cm³
• LogP: 3.93640
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 220.182715385
• Heavy Atom Count: 16
• Complexity: 330

Purity/Quality:

β-CaryophylleneEpoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2C1CCC3(C(O3)CCC2=C)C)C
• Uses: β-Caryophyllene Epoxide, and its derivatives has shown to have microbial transformation and butyrylcholinesterase inhibitory activity. It is also the main active constituent of essential oils obtained from various plants, used for flavoring and fragrances.

Technology Process of Caryophyllene epoxide

There total 24 articles about Caryophyllene epoxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

β-caryophyllene (87-44-5) → Caryophyllene oxide (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)

Guidance literature:

With sodium hydroxide; sodium tungstate; phenylphosphonate; dihydrogen peroxide; methyl tri-n-octyl ammonium hydrogen sulfate; In water; at 25 ℃; for 12h;

DOI:10.1055/s-0028-1088156

Reference yield: 79.0%

β-caryophyllene (87-44-5,118-65-0,10579-93-8,13877-93-5,17627-40-6,54061-81-3,61217-74-1,68832-35-9,89575-63-3) → (1R,6R,10S)-5,12,12-Trimethyl-9-methylene-4-oxa-tricyclo[8.2.0.03,5]dodecan-6-ol (88514-14-1) + caryophyllenol-II (19431-76-6,19431-77-7,32214-88-3,32214-89-4,34298-31-2,38284-08-1,73088-51-4) + caryophyllene epoxide (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)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 ℃; for 6h;

DOI:10.1016/S0040-4020(01)91590-X

Reference yield: 74.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (1R,4R,6R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodcan-9-one (10306-22-6,10306-31-7,24173-71-5,34175-71-8) → caryophyllene oxide (1139-30-6)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 0.166667h;

(1R,4R,6R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^4,6]dodcan-9-one; In tetrahydrofuran; at -78 - 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2016.08.079

upstream raw materials:

β-caryophyllene

(1S,4S,7R)-7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulene

acetic acid

Perbenzoic acid

Downstream raw materials:

(1R,4R,6R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^4,6]dodcan-9-one

clovanediol

(β,9β)-caryolane-1,9-diol

(1R,5S,8R,9R)-4,4,8-trimethylbicyclo<6.3.1.0^1,5>dodeca-2-en-9-ol

Refernces

• 1、 dos Santos Costa, Maíra,de Camargo Faria, Amanda,Mota, Rayssa L.V.,Gusevskaya, Elena V.. "A further step to sustainable palladium catalyzed oxidation: Allylic oxidation of alkenes in green solvents". . . Retrieved 2021/09/14.
• 2、 Li, Shiye,Shi, Lihan,Zhang, Li,Huang, Hongmei,Xiao, Yi,Mao, Liqiu,Tan, Rong,Fu, Zaihui,Yu, Ningya,Yin, Dulin. "Ionic liquid-mediated catalytic oxidation of β-caryophyllene by ultrathin 2D metal-organic framework nanosheets under 1 atm O2". . . Retrieved 2020/09/16.