Corynanthine

Base Information

• Chemical Name: Corynanthine
• CAS No.: 483-10-3
• Molecular Formula: C21H26 N2 O3
• Molecular Weight: 354.449
• European Community (EC) Number: 207-590-0
• UNII: F5Z7C9RK8U
• DSSTox Substance ID: DTXSID401317915
• Nikkaji Number: J5.984F
• Wikipedia: Corynanthine
• Wikidata: Q5173746
• Pharos Ligand ID: GL6GLST6PML7
• ChEMBL ID: CHEMBL31410
• Mol file: 483-10-3.mol

Synonyms:Aphrodine Hydrochloride;Aphrodyne;Corynanthine;Corynanthine Tartrate;Hydrochloride, Aphrodine;Hydrochloride, Yohimbine;Pluriviron;Rauhimbine;Rauwolscine;Tartrate, Corynanthine;Yocon;Yohimbin Spiegel;Yohimbine;Yohimbine Houdé;Yohimbine Hydrochloride;Yohimex

Chemical Property of Corynanthine

Chemical Property:

• Vapor Pressure: 1.27E-12mmHg at 25°C
• Melting Point: 225-230°C
• Boiling Point: 543°Cat760mmHg
• Flash Point: 282.2°C
• PSA: 65.56000
• Density: 1.31g/cm³
• LogP: 2.58500
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 354.19434270
• Heavy Atom Count: 26
• Complexity: 555

Purity/Quality:

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

Corynanthine ^*data from reagent suppliers

Safty Information:

• Statements: 25
• Safety Statements: 1-20-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
• Isomeric SMILES: COC(=O)[C@@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O
• Description: This alkaloid has been isolated by Hoffmann from the bark of Rauwolfia serpentina. It forms colourless crystals from Me2CO and has [α]20D - 82° (c 0.5, pyridine).

Technology Process of Corynanthine

There total 36 articles about Corynanthine 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: 52.9%

methyl (16α)-17-oxoyohimban-16-carboxylate (2114-90-1,2671-55-8,2671-57-0,18210-73-6,24204-01-1,40088-11-7,41904-77-2,59952-51-1,67711-33-5,83540-87-8,89015-76-9,114030-03-4) → (+/-)-β-yohimbine (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7) + 3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00008a025

Reference yield: 52.9%

methyl (16α)-17-oxoyohimban-16-carboxylate (2114-90-1,2671-55-8,2671-57-0,18210-73-6,24204-01-1,40088-11-7,41904-77-2,59952-51-1,67711-33-5,83540-87-8,89015-76-9,114030-03-4) → (+/-)-β-yohimbine (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7) + 3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00008a025

Reference yield:

→ corynanthine (483-10-3)

Guidance literature:

Darstellung aus der Rinde;

upstream raw materials:

methyl (16α)-17-oxoyohimban-16-carboxylate

19,20-didehydroyohimban-17-one

(20β)-18,19-didehydroyohimban-17-one

dimethyl (16α)-17-oxoyohimban-1,16-dicarboxylate

Downstream raw materials:

17α-hydroxy-16β-methoxycarbonyl-4ξ-methyl-yohimbanium; iodide

Apoyohimbin

Yohimbine

17α-hydroxy-yohimban-16α-carboxylic acid ethyl ester

Refernces

• 1、 Miyata,Hirata,Naito,Ninomiya. "Novel total syntheses of (±)-yohimbine and (±)-alloyohimbine". . p. 1231 - 1232. Retrieved 2007/10/02.
• 2、 Szantay,Toeke,Honti. "Synthesis of (+)-yohimbine and (+)-beta-yohimbine. A new route to yohimban ring system.". . p. 1665 - 1670. Retrieved 2007/10/04.