(-)-alpha-Copaene

Base Information

• Chemical Name: (-)-alpha-Copaene
• CAS No.: 3856-25-5
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• European Community (EC) Number: 223-364-4
• Mol file: 3856-25-5.mol

Synonyms:alpha-copaene

Chemical Property of (-)-alpha-Copaene

Chemical Property:

• Vapor Pressure: 0.038mmHg at 25°C
• Melting Point: 74 °C
• Refractive Index: n20/D 1.490
• Boiling Point: 248.5°Cat760mmHg
• Flash Point: 105.1°C
• PSA: 0.00000
• Density: 0.939g/cm³
• LogP: 4.27090
• Storage Temp.: −20°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 312

Purity/Quality:

99%, ^*data from raw suppliers

α-Copaene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC2C3C1C2(CCC3C(C)C)C
• Isomeric SMILES: CC1=CCC2C3C1[C@@]2(CCC3C(C)C)C
• Description: α-Copaene is a sesquiterpene found in a variety of plants, including Cannabis, that has antiproliferative and antioxidant properties. It inhibits proliferation of primary rat neurons and N2a rat neuroblastoma cells in a concentration-dependent manner and cultured human lymphocytes when used at concentrations greater than 100 mg/L. α-Copaene (25 mg/L) increases total antioxidant capacity in primary rat neurons and N2a neuroblastoma cells, as well as cultured human lymphocytes, when used at concentrations of 50 and 100 mg/L.
• Uses: α-Copaene is a tricyclic?sesquiterpenes?and can be extracted from the oil of S. aethiopis. It also exhibit anti-plasmodial activity against?P. falciparum in culture.

Technology Process of (-)-alpha-Copaene

There total 16 articles about (-)-alpha-Copaene 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: 47.0%

(+/-)-β-copaene (18252-44-3,20479-06-5,28129-91-1,29484-26-2,41530-63-6,41530-64-7,70115-82-1,147515-11-5) → α-copaene (947-59-1,3856-25-5,13567-62-9,14912-44-8,15493-66-0,15917-91-6,138874-68-7)

Guidance literature:

With hydrogen iodide; In benzene; for 0.75h;

Reference yield: 2.5%

germacrene D (105453-16-5) → (±)-δ-cadinene (483-76-1,13061-82-0,16729-01-4,20085-20-5,60305-17-1,73365-79-4) + α-copaene (947-59-1,3856-25-5,13567-62-9,14912-44-8,15493-66-0,15917-91-6,138874-68-7) + γ-cadinene (39029-41-9) + γ-muurolene (30021-74-0)

Guidance literature:

With silica gel; In hexane; for 48h; Further byproducts given;

DOI:10.1016/S0031-9422(00)00266-1

Reference yield:

(2-cis,6-trans)-farnesyl diphosphate (40716-68-5) → β-himachalene (1461-03-6) + α-himachalene (3853-83-6) + 2-himachalen-7-ol (1891-45-8) + α-ylangene (947-59-1,3856-25-5,13567-62-9,14912-44-8,15493-66-0,15917-91-6,138874-68-7) + γ-cis-himachalane (53111-25-4) + humula-4,9-dien-8-ol + isobicyclogermacrene + γ-humulene + δ–amorphene + α-Amorphene

Guidance literature:

With Medicago truncatula multiproduct sesquiterpene synthase; In pentane; at 30 ℃; for 1.5h; pH=7.5; stereospecific reaction; Enzymatic reaction;

DOI:10.1021/acs.joc.6b02696

upstream raw materials:

(2-cis,6-trans)-farnesyl diphosphate

copan-3-ol

(+/-)-β-copaene

germacrene D

Downstream raw materials:

isosativene

(-)-α-muurolene

calamenene

delta-cadinene

Refernces

• 1、 Garms, Stefan,Koellner, Tobias G.,Boland, Wilhelm. "A multiproduct terpene synthase from medicago truncatula generates cadalane sesquiterpenes via two different mechanisms". supporting information; experimental part. p. 5590 - 5600. Retrieved 2010/11/20.
• 2、 Wenkert, Ernest,Bookser, Brett C.,Arrbenius, Thomas S.. "Total syntheses of (±)-α- And (±)-β-copaene and formal total syntheses of (±)-sativene, (±)-cis-sativenediol, and (±)-helminthosporal". . p. 644 - 654. Retrieved 2007/10/02.