482-85-9

Basic information

• Product Name: (-)-ISORESERPINE
• Synonyms: (-)-ISORESERPINE;(20α)-18β-(3,4,5-Trimethoxybenzoyloxy)-11,17α-dimethoxyyohimban-16β-carboxylic acid methyl ester;20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester) (8ci);3-Epireserpine;Isoreserpin;Nsc 80138;Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)-, methyl ester, (16beta,17alpha,18beta,20alpha)- (9ci);methyl (1S,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• CAS NO: 482-85-9
• Molecular Formula: C₃₃H₄₀N₂O₉
• Molecular Weight: 608.68
• Product Categories: Asymmetric Synthesis;Chiral Building Blocks;Complex Molecules
• Mol File: 482-85-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 148-155 °C(lit.)
• Boiling Point: 700.1°Cat760mmHg
• Flash Point: 377.2°C
• Appearance: /
• Density: 1.32g/cm³
• PKA: 18.11±0.70(Predicted)
• CAS DataBase Reference: (-)-ISORESERPINE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ISORESERPINE(482-85-9)
• EPA Substance Registry System: (-)-ISORESERPINE(482-85-9)

Safety Data

• RIDADR: UN 1544 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 482-85-9(Hazardous Substances Data)

Usage

General Description

(-)-Isorerpine is a chemical compound that is an alkaloid derived from the Rauwolfia plant. It is a stereoisomer of reserpine and has similar pharmacological effects, including acting as a dopamine receptor antagonist and a serotonin receptor antagonist. It is primarily used as an antihypertensive agent, as it reduces blood pressure by inhibiting the sympathetic nervous system. It also has potential antipsychotic and sedative properties, making it useful in the treatment of certain mental health disorders. However,

Upstream product

• 50-55-5 reserpine 
• 75276-07-2 (1S,2R,3R,4aS,13bS,14aS)-8a-Hydroxy-2,11-dimethoxy-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester 
• 68104-24-5 6-methoxy-tryptophyl bromide 
• 41340-31-2 2-(6-methoxy-1H-indol-3-yl)ethan-1-ol 
• 68104-22-3 (6-methoxy-1H-indol-3-yl)(oxo)acetyl chloride 
• 75276-03-8 Acetic acid (4aS,5R,6R,7R,8aS)-7-acetoxy-6-methoxy-decahydro-isoquinolin-5-ylmethyl ester 
• 75276-04-9 2,3-secoreserpinediol 
• 112547-24-7 (4aS,5S,6R,7R,8aS)-6-Methoxy-7-(3,4,5-trimethoxy-benzoyloxy)-octahydro-isoquinoline-2,5-dicarboxylic acid dimethyl ester 
• 6242-28-0 3,4,5-Trimethoxy-benzoic acid (1R,2R,3R,4aS,13bS,14aS)-1-hydroxymethyl-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-3-yl ester 
• 75276-06-1 3,4,5-Trimethoxy-benzoic acid (1S,2R,3R,4aS,13bS,14aS)-1-formyl-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-3-yl ester 
• 75276-05-0 C₄₂H₅₀N₂O₁₂ 
• 75276-01-6 (4aS,5R,6R,7R,8aS)-7-Acetoxy-5-acetoxymethyl-6-methoxy-octahydro-isoquinoline-2-carboxylic acid methyl ester 
• 16625-53-9 2,3-secoreserpine 
• 1195701-29-1 isoreserpinediol 

Downstream Products

• 50-55-5 reserpine 
• 16625-52-8 C₃₃H₄₂N₂O₉ 
• 16625-53-9 2,3-secoreserpine 

Relevant articles and documents

A Desymmetrization-Based Total Synthesis of Reserpine

Reported herein is a desymmetrization-based synthetic approach to the fused polycyclic indole alkaloid reserpine. The centerpiece of the developed strategy features an internal desymmetrization process that enabled the use of a readily accessible and nonstereogenic reserpine E-ring precursor, in contrast to the synthesis-intensive and stereodefined E-ring intermediates employed in all past reserpine syntheses. Utilization of inexpensive reagents through an orchestrated sequence of carefully selected chemical transformations further highlight the overall effectiveness of the developed pathway.

Novel zinc mediated indole ring opening of isoreserpine

Reaction of reserpine'(1) with Zn/TFA resulted in isoreserpine (2), dihydro compound (7), and amino compound (8) via initial epimerization at C- 3. The latter two compounds constitute a novelty in indole alkaloid chemistry: the dihydro compound (7) posses

Genaral Strategies for the Synthesis of Indole Alkaloids. Total Syntheses of (+/-)-Reserpine and (+/-)-α-Yohimbine

The concise, total syntheses of the indole alkaloids (+/-)-reserpine (1) and (+/-)-α-yohimbine (4) have been completed by the application of a general strategy that features an intramolecular Diels-Alder reaction for the facile construction of the functio