(+)-LEDENE

Base Information

• Chemical Name: (+)-LEDENE
• CAS No.: 21747-46-6
• Deprecated CAS: 40520-60-3
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• European Community (EC) Number: 244-565-3
• UNII: 236ZZ41F70
• DSSTox Substance ID: DTXSID60944355
• Nikkaji Number: J15.850J
• Wikidata: Q27132626
• Metabolomics Workbench ID: 62782
• Mol file: 21747-46-6.mol

Synonyms:1H-Cycloprop[e]azulene,1a,2,3,5,6,7,7a,7b-octahydro-1,1,4,7-tetramethyl-, (+)- (8CI);1H-Cycloprop[e]azulene, 1a,2,3,5,6,7,7a,7b-octahydro-1,1,4,7-tetramethyl-,[1aR-(1aa,7a,7ab,7ba)]-; Ledene (6CI); (+)-Ledene;Leden; Viridiflorene

Chemical Property of (+)-LEDENE

Chemical Property:

• Vapor Pressure: 0.0164mmHg at 25°C
• Melting Point: 269°C
• Refractive Index: n20/D 1.504
• Boiling Point: 268-270 °C(lit.)
• Flash Point: 101.3°C
• PSA: 0.00000
• Density: 0.927 g/mL at 20 °C(lit.)
• LogP: 4.41500
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Ethanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 321

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+)-Ledene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2=C(CCC3C(C12)C3(C)C)C
• Isomeric SMILES: C[C@@H]1CCC2=C(CC[C@@H]3[C@H]([C@H]12)C3(C)C)C
• Uses: (+)-Ledene is an essential oil that is synthesized by viridiflorene synthase. It has been studied as an antioxidant, antimicrobial, antibiofilm and to treat various cancers.

Technology Process of (+)-LEDENE

There total 12 articles about (+)-LEDENE 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: 90.0%

ledol (489-41-8,552-02-3,577-27-5,19078-39-8,51371-47-2,55659-76-2,64366-31-0,64665-36-7,77171-54-1,88728-58-9,133443-04-6,146864-34-8) → ledene (21747-46-6,74409-93-1,77171-52-9,128779-67-9)

Guidance literature:

With pyridine; trichlorophosphate; at 0 ℃; for 7h;

DOI:10.1007/BF00629824

Reference yield: 80.0%

(+)-aromadendrene (489-39-4) → [1aR-(1aα,7α,7aβ,7bα)]-1a,2,3,5,6,7,7a,7b-octahydro-1,1,4,7-tetramethyl-1H-cycloprop[e]azulene (74409-93-1,77171-52-9,128779-67-9,21747-46-6)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 100 ℃;

DOI:10.1016/S0040-4020(03)01231-6

Reference yield: 52.0%

(+)-bicyclogermacrene (41437-00-7,67650-49-1,67650-90-2,79951-53-4,100762-45-6,100762-46-7,100762-48-9,100762-49-0,133005-43-3,24703-35-3) → [1aR-(1aα,7α,7aβ,7bα)]-1a,2,3,5,6,7,7a,7b-octahydro-1,1,4,7-tetramethyl-1H-cycloprop[e]azulene (74409-93-1,77171-52-9,128779-67-9,21747-46-6)

Guidance literature:

With potassium hydrogensulfate; potassium thioacyanate; In chloroform; for 0.0833333h; Inert atmosphere;

DOI:10.1002/chem.201403082

upstream raw materials:

(+)-aromadendrene

pittosporanoside A₁

(+)-aromadendrene

(+)-bicyclogermacrene

Downstream raw materials:

aromadendr-1⁽¹⁰⁾-en-9-one

Refernces

• 1、 Moreno-Dorado, F. Javier,Lamers, Yvonne M. A. W.,Mironov, Grigore,Wijnberg, Joannes B. P. A.,De Groot, Aede. "Chemistry of (+)-aromadendrene. Part 6: Rearrangement reactions of ledene, isoledene and their epoxides". . p. 7743 - 7750. Retrieved 2007/10/03.
• 2、 Takaoka, Daisuke,Kawahara, Hiroshi,Ochi, Shima,Hiroi, Mitsuru,Nozaki, Hiroshi,et al.. "THE STRUCTURES OF SESQUITERPENE GLYCOSIDES FROM Pittosporum tobira Ait". . p. 1121 - 1124. Retrieved 2007/10/02.