483-09-0

Basic information

• Product Name: (3β,20α)-17α-Hydroxyyohimban-16β-carboxylic acid methyl ester
• Synonyms: (3β,20α)-17α-Hydroxyyohimban-16β-carboxylic acid methyl ester;3-Epi-α-yohimbine;Isorauhimbine;epi-3alpha-Yohimbine
• CAS NO: 483-09-0
• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.44274
• Mol File: 483-09-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 543 °C at 760 mmHg
• Flash Point: 282.2 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 1.27E-12mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: (3β,20α)-17α-Hydroxyyohimban-16β-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3β,20α)-17α-Hydroxyyohimban-16β-carboxylic acid methyl ester(483-09-0)
• EPA Substance Registry System: (3β,20α)-17α-Hydroxyyohimban-16β-carboxylic acid methyl ester(483-09-0)

Safety Data

• Hazardous Substances Data: 483-09-0(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15+,17-,18+,19+/m1/s1

Upstream product

• 81750-86-9 19,20-didehydroyohimban-17-one 
• 37734-05-7 Methyl 3-oxo-4-pentenoate 
• 1218-41-3 1-<2-(1H-indol-3-yl)ethyl>-4-piperidinone 
• 36069-26-8 methyl (20α)-15,16-didehydro-17-oxoyohimban-16-carboxylate 
• 36069-26-8 methyl (20β)-15,16-didehydro-17-oxoyohimban-16-carboxylate 
• 132672-67-4 2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4-methoxypyridinium trifluoromethanesulfonate 
• 132672-75-4 methyl 1,2,6,7,8,8a-hexahydro-2-<2-(1H-indol-3-yl)ethyl>-6-oxo-5-isoquinolinecarboxylate 
• 37734-07-9 methyl endo/exo-3-(bicyclo<2,2,1>hept-5-en-2-yl)-3-oxopropanoate 
• 92579-46-9 2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4(1H)-pyridinone 
• 26822-37-7 N,N-dimethyl-4-oxopiperidinium iodide 
• 61-54-1 tryptamine 
• 2114-90-1 methyl (16α)-17-oxoyohimban-16-carboxylate 
• 88966-92-1 dimethyl (16α)-17-oxoyohimban-1,16-dicarboxylate 
• 54725-64-3 (20β)-18,19-didehydroyohimban-17-one 

Downstream Products

• 574-60-7 3-(3-Ethylindol-2-yl)-5,6,7,8-tetrahydroisoquinoline 
• 146-48-5 Yohimbine 
• 131-03-3 rauwolscine 

Relevant articles and documents

Total Syntheses of Yohimbe Alkaloids, with Stereoselection for the Normal, Allo, and 3-Epiallo Series, Based on Annelations of 4-Methoxy-1,2-dihydropyridones

N--2,3-dihydro-4-pyridone (31) was generated in two steps (77percent yield) from tryptamine and N-methyl-4-piperidone methiodide.Its cyclization (90percent yield) and oxidation (91percent yield) provided the tetracyclic analogue 32.O-Methylation and Robinson-type annelation of these vinylogous lactams (the latter in form of its Na-carbamate) furnished the dienones 38 (64percent) and 43 (90percent).Further elaboration by cyclization and/or reduction reactions selectively provided the 15,16-didehydroyohimbinones 7 and 44.Their reductions then led to yohimbinone (52, 20percent overall yield from tryptamine), alloyohimbinone (11, 19percent overall yield), and 3-epi-alloyohimbinone (10, 23percent overall yield), which led to yohimbine (3), β-yohimbine (9), 3-epi-alloyohimbine (53), and 3-epi-17-epi-alloyohimbine (54).

Total synthesis of yohimbine.

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