Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-

Base Information

• Chemical Name: Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
• CAS No.: 87-44-5
• Molecular Formula: C15H24
• Molecular Weight: 206.371
• Hs Code.: 29021990
• European Community (EC) Number: 201-746-1
• Wikipedia: Caryophyllene
• Wikidata: Q105183234
• RXCUI: 1368148
• Mol file: 87-44-5.mol

Synonyms:Caryophyllene;87-44-5;Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-

Chemical Property of Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-

Chemical Property:

• Appearance/Colour: Pale yellow oily liquid with an odor midway between odor of cloves and turpentine.
• Vapor Pressure: 0.0453mmHg at 25°C
• Melting Point: <25℃
• Refractive Index: n20/D 1.5(lit.)
• Boiling Point: 268.359 °C at 760 mmHg
• Flash Point: 104.917 °C
• PSA: 0.00000
• Density: 0.894 g/cm³
• LogP: 4.72520
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: <0.1 g/100 mL at 21 C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 293

Purity/Quality:

85%min , ^*data from raw suppliers

β-Caryophyllene ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC1=CCCC(=C)C2CC(C2CC1)(C)C
• Isomeric SMILES: CC1=CCCC(=C)[C@H]2CC([C@@H]2CC1)(C)C
• Description: β-Caryophyllene (Item No. 21572) is a sesquiterpene that has been found in plants, including C. sativa, C. indica, and hemp, and has diverse biological activities, including lipid metabolic, antioxidant, anti-neuroinflammatory, anti-proliferative, and antinociceptive properties. It is an agonist of the cannabinoid (CB) receptor CB2 (Ki = 155 nM) that inhibits cAMP production induced by forskolin in CHO-K1 cells expressing CB2 receptors (EC50 = 38 nM). β-Caryophyllene is also an agonist of peroxisome proliferator-activated receptor α (PPARα; EC50 = 9.58 μM in a reporter assay). β-Caryophyllene (1 and 2.5 μM) reduces the production of reactive oxygen species (ROS) in and protects against cytotoxicity of SH-SY5Y cells induced by 1-methyl-4-pheylpyridinium (MPP+). It also decreases the β-amyloid burden in the hippocampus and cerebral cortex and improves memory in an APP/PS1 transgenic mouse model of Alzheimer’s disease, decreasing the latency to find the platform in the Morris water maze during training and increasing the time spent in the target quadrant during testing when administered at a dose of 48 mg/kg per day. β-Caryophyllene (50 mg/kg) increases the number of entries into and the time spent in the open arms of the elevated plus maze and the time spent immobile in the forced swim test, indicating anxiolytic-like and antidepressant-like activity, effects that can be blocked by the CB2 receptor antagonist AM630 .
• Uses: β-Caryophyllene is notable for having a cyclobutane ring, a rarity in nature. β-Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. β-Caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.

Technology Process of Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-

There total 23 articles about Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- 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: 79.0%

(1S,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-(5E)-en-2-one (60362-44-9) + Methyltriphenylphosphonium bromide (1779-49-3) → β-caryophyllene (87-44-5)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 23 ℃;

(1S,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-(5E)-en-2-one; In tetrahydrofuran; hexane; at 23 ℃; for 1h; Further stages.;

DOI:10.1021/ja8003705

Reference yield: 70.0%

(E)-caryophyll-4-en-8-yl p-nitrobenzoate → β-caryophyllene (87-44-5) + (1S,2R,5R,6S,9R)-2,6,10,10-tetramethyltricyclo<7.2.0.02,5>undecan-6-ol (169220-06-8) + (1S,2R,9R,E)-2,6,10,10-tetramethylbicyclo[7.2.0]undec-5-en-2-ol (60269-12-7)

Guidance literature:

With water; In pyridine; acetone; at 125 ℃; for 2h;

DOI:10.1021/jo971984m

Reference yield: 45.0%

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → α-caryophyllene (6753-98-6) + β-caryophyllene (87-44-5) + 9‐epi‐(E)‐caryophyllene (68832-35-9) + 2-((1S,3aS,7aS,E)-1,6,6-trimethyloctahydro-4H-inden-4-ylidene)propan-1-ol + (+)-isoafricanol (104975-19-1) + african-1-ene + δ9,10-africanene

Guidance literature:

With sesquiterpene cyclase from Trichoderma spp.; In aq. buffer; at 28 ℃; for 3h; pH=8.2; Enzymatic reaction;

DOI:10.1002/anie.201907964

upstream raw materials:

4,5-epithiocaryophyllene

caryophyllene oxide

14-hydroxy-4,5-dihydro-caryophyllene

farnesyl pyrophosphate

Downstream raw materials:

caryophyllene oxide

Caryophyllinnitrosit

hydrocaryophyllene

(β,9β)-caryolane-1,9-diol

Refernces

• 1、 -. "Method and Means for Releasing a Terpene Mixture to a Cannabis Flower During Storage". . . Retrieved 2021/09/17.
• 2、 Bissegger, Fabian,Levi, Shani,Major, Dan T.,Némethová, Ivana,Prescimone, Alessandro,Schmid, Dario,Syntrivanis, Leonidas-Dimitrios,Tiefenbacher, Konrad. "Four-Step Access to the Sesquiterpene Natural Product Presilphiperfolan-1β-ol and Unnatural Derivatives via Supramolecular Catalysis". . p. 5894 - 5900. Retrieved 2020/04/10.