Ophiocarpine

Base Information

• Chemical Name: Ophiocarpine
• CAS No.: 478-13-7
• Molecular Formula: C20H21NO5
• Molecular Weight: 355.3844
• ChEMBL ID: CHEMBL1556795
• Nikkaji Number: J12.352H
• Wikidata: Q104396225
• Mol file: 478-13-7.mol

Synonyms:ophiocarpine

Chemical Property of Ophiocarpine

Chemical Property:

• Vapor Pressure: 1.54E-11mmHg at 25°C
• Melting Point: 188°C
• Boiling Point: 517.6°Cat760mmHg
• Flash Point: 266.8°C
• PSA: 60.39000
• Density: 1.41g/cm³
• LogP: 2.51680
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 355.14197277
• Heavy Atom Count: 26
• Complexity: 518

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(C=C1)C(C3C4=CC5=C(C=C4CCN3C2)OCO5)O)OC
• Isomeric SMILES: COC1=C(C2=C(C=C1)[C@H]([C@H]3C4=CC5=C(C=C4CCN3C2)OCO5)O)OC
• Description: This protoberberine alkaloid is the major constituent of Corydalis ophiocarpa Hook. It has [α] 24 D - 284° (CHC13) and yields a sparingly soluble hydrochloride; a methiodide, m.p. 271°C (dec.) and the O-acetate, m.p. l41-3°C (165-7°C). It contains two methoxyl groups and one methylenedioxy group and when boiled with HCl furnishes a yellow base which, on oxidation with iodine and subsequent reduction, is converted into (±)-Canadine (q.v.). The alkaloid is therefore 13- hydroxycanadine, a structure confirmed by its oxidation to 6:7-methylenedioxy_x0002_l-keto-1: 2: 3 :4-tetrahydroisoquinoline (noroxyhydrastinine), m.p. 183°C, with KMn04' The optically inactive form crystallizes as colourless needles from MeOH-CHC13 , m.p. 252°C and also gives an O-acetate as needles from petroleum ether, m.p. 172-4°C.

Technology Process of Ophiocarpine

There total 4 articles about Ophiocarpine 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:

(-)-β-hydrastine (118-08-1,4370-85-8,29617-43-4,53950-51-9,60594-55-0,60827-73-8,73554-66-2,85280-16-6,85280-18-8) → (-)-Ophiocarpin (478-13-7)

Guidance literature:

Reaktion ueber mehrere Stufen;

Reference yield:

→ 13-Epiophiocarpine; 13-Epihydroxy-2,3-methylendioxy-9,10-dimethoxy-5,6,13,13a-tetrahydro-8H-dibenzochinolizin (478-13-7,5308-61-2,18090-55-6,18090-57-8,100101-07-3)

Guidance literature:

Ophiocarpine-methochlorid b. 205-210grad/2-3 Torr;

Reference yield:

→ 13-Epiophiocarpin (478-13-7,5308-61-2,18090-55-6,18090-57-8,100101-07-3)

Guidance literature:

Dihydroberberin mit Diboran in THF (20grad, mehrere Std.), Hydrolyse, 20percentig. wss. NaOH u. 30percentig. H2O2 (20grad, 3 Std.);

upstream raw materials:

(-)-β-hydrastine