Isorauhimbine

Base Information

• Chemical Name: Isorauhimbine
• CAS No.: 483-09-0
• Molecular Formula: C21H26N2O3
• Molecular Weight: 354.449
• Nikkaji Number: J12.799J
• Wikidata: Q104393944
• ChEMBL ID: CHEMBL465600
• Mol file: 483-09-0.mol

Synonyms:Isorauhimbine;3-Epiisoyohimbine;483-09-0;3-epi-alpha-Yohimbine;methyl (1R,15S,18S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;Isorauhimbin;Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (3beta,16beta,17alpha,20alpha)-;3-Epirauwolscine;3-epi-Rauwolscine;CHEMBL465600;SCHEMBL20139010;AKOS032962168

Chemical Property of Isorauhimbine

Chemical Property:

• Vapor Pressure: 1.27E-12mmHg at 25°C
• Refractive Index: 1.66
• Boiling Point: 543 °C at 760 mmHg
• Flash Point: 282.2 °C
• PSA: 65.56000
• Density: 1.31 g/cm³
• LogP: 2.58500
• 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:

99% ^*data from raw suppliers

Isorauhimbin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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
• Uses: Isorauhimbin, is a novel plant-derived molecule of Rauvolfia serpentina that can be used as an inhibitor of aldose reductase, a potent drug target for diabetes and its complications.

Technology Process of Isorauhimbine

There total 35 articles about Isorauhimbine 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:

tryptamine (61-54-1) → 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:

Multi-step reaction with 7 steps

1: 90 percent / potassium carbonate / ethanol; H₂O / 0.5 h / Heating

2: 1) m-(chloroperoxy)benzoic acid, 2) triethylamine, acetic anhydride / 1) diethyl ether/dichloromethane, 0 to 20 deg C, 2 h, 2) CH₂Cl₂, 0 deg C, 30 min

3: 95 percent / CH₂Cl₂ / 0.5 h / 20 °C

4: 1) 1,4-diazabicyclo<5.4.0>undec-7-ene (DBU) / 1) N,N-dimethylacetamide, 2) a) 20 deg C, 1h, b) 70 deg C, 1h

5: 50 percent / 50percent aq. sulfuric acid / methanol / 24 h / 20 °C

6: 65.6 percent / conc. hydrochloric acid, H₂ / 10percent Pd-C / methanol / 18 h / 20 °C / 760 Torr

7: 22.2 percent / sodium borohydride / methanol / 0.33 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; 1,4-diazabicyclo[5.4.0]-7-undecene; sulfuric acid; hydrogen; acetic anhydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water;

DOI:10.1021/jo00008a025

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:

3-(3-Ethylindol-2-yl)-5,6,7,8-tetrahydroisoquinoline

Yohimbine

rauwolscine

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.