Cycleanine

Base Information

• Chemical Name: Cycleanine
• CAS No.: 518-94-5
• Molecular Formula: C₃₈H₄₂N₂O₆
• Molecular Weight: 622.761
• UNII: BN8R5T4KQ9
• DSSTox Substance ID: DTXSID40199740
• Nikkaji Number: J18.010F
• Wikipedia: Cycleanine
• Wikidata: Q15410908
• ChEMBL ID: CHEMBL443389
• Mol file: 518-94-5.mol

Synonyms:cycleanine;isocycleanine

Chemical Property of Cycleanine

Chemical Property:

• Melting Point: 272-273 °C
• Boiling Point: 691.6°Cat760mmHg
• PKA: 7.56±0.20(Predicted)
• Flash Point: 169.8°C
• PSA: 61.86000
• Density: 1.172g/cm³
• LogP: 7.03820
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 622.30428706
• Heavy Atom Count: 46
• Complexity: 895

Purity/Quality:

≥98% ^*data from raw suppliers

Cycleanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C3=C2C1CC4=CC=C(C=C4)OC5=C6C(CC7=CC=C(O3)C=C7)N(CCC6=CC(=C5OC)OC)C)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C3=C2[C@H]1CC4=CC=C(C=C4)OC5=C6[C@@H](CC7=CC=C(O3)C=C7)N(CCC6=CC(=C5OC)OC)C)OC)OC
• Uses: Cycleanine is an alkaloid obtained from the Triclisia subcordata Oliv (Menispermeaceae) which is a medicinal plant used to treat various diseases in West Africa. Displays in-vitro anti-ovarian cancer activity.

Technology Process of Cycleanine

There total 8 articles about Cycleanine 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: 70.0%

cycleanine β-N-oxide → (-)-cycleanine (518-94-5,10438-14-9,18210-67-8,30745-31-4,68778-89-2)

Guidance literature:

With sulphurous acid; In water; for 8h; Ambient temperature;

DOI:10.1021/np970362t

Reference yield:

3,4-dehydrocycleanine → (-)-cycleanine (518-94-5,10438-14-9,18210-67-8,30745-31-4,68778-89-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4h; Ambient temperature;

DOI:10.1248/cpb.45.470

Reference yield:

cycleanine α-N-oxide → (-)-cycleanine (518-94-5,10438-14-9,18210-67-8,30745-31-4,68778-89-2)

Guidance literature:

With sulphurous acid; In water; for 8h; Ambient temperature;

DOI:10.1021/np970362t

upstream raw materials:

diazomethane

(R,R)-isochondodendrine

formaldehyd

formic acid

Downstream raw materials:

armepavine

(R,R)-isochondodendrine

Refernces

• 1、 Kashiwaba, Noriaki,Morooka, Shigeo,Kimura, Michiko,Murakoshi, Yoshie,Ono, Minoru,Toda, Jun,Suzuki, Hideki,Sano, Takehiro. "Alkaloidal constituents of the tubers of Stephania cepharantha cultivated in Japan: Structure of 3,4-dehydrocycleanine, a new bisbenzylisoquinoline alkaloid". . p. 470 - 475. Retrieved 2007/10/03.