483-34-1

Basic information

• Product Name: (S)-Isocorypalmine
• Synonyms: (-)-Isocorypalmine;(13aS)-3,9,10-Trimethoxy-5,6,13,13a-tetrahydro-8H-dibenzo[a,g]quinolizine-2-ol;(S)-Isocorypalmine;[13aS,(-)]-5,8,13,13a-Tetrahydro-3,9,10-trimethoxy-6H-dibenzo[a,g]quinolizine-2-ol;l-Isocorypalmine;l-Tetrahydrocolumbamine;(13aS)-5,8,13,13a-Tetrahydro-3,9,10-trimethoxy-6H-dibenzo[a,g]quinolizin-2-ol;(S)-Tetrahydrocolumbamine
• CAS NO: 483-34-1
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.40100
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 483-34-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 240-241℃
• Boiling Point: 501.2°C at 760 mmHg
• Flash Point: 256.9°C
• Appearance: /
• Density: 1.29
• Vapor Pressure: 1.14E-10mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Heated), Ethyl Acetate (Slightly, Heated)
• PKA: 10.18±0.20(Predicted)
• CAS DataBase Reference: (S)-Isocorypalmine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Isocorypalmine(483-34-1)
• EPA Substance Registry System: (S)-Isocorypalmine(483-34-1)

Safety Data

• Hazardous Substances Data: 483-34-1(Hazardous Substances Data)

Usage

Description

This Menispermaceous alkaloid is found in the EtOH extract of Bornean Tino_x0002_miscium petiolare and crystallizes as colourless crystals from Me2CO. The 0- methyl derivative is identical with (-)-Tetrahydropalmatine, m.p. 141-2°C.

Uses

A metabolite of the isoquinoline alkaloid biosynthesis pathway.

References

Tomita, Furukawa.,J. Pharm. Soc., Japan, 87,881 (1967)

InChI:InChI=1/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-17(22)19(24-2)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m0/s1

Upstream product

• 3621-36-1 columbamine 
• 186581-53-3 diazomethane 
• 2934-97-6 (+/-)-tetrahydropalmatine 
• 605-34-5 (S)-scoulerine 
• 485-19-8 (+)-(S)-reticuline 
• 483-14-7 tetrahydropalmatine 
• 1422431-12-6 6-(2-(3,4-dimethoxyphenethylamino)-2-oxoethyl)-2,3-dimethoxyphenyl acetate 
• 1422431-15-9 (S)-6-((6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-2,3-dimethoxylbenzyl acetate 
• 63909-38-6 3-methoxy-4-benzyloxy-ω-nitrostyrolene 
• 1422431-55-7 (S)-2-benzyloxy-3,9,10-trimethoxytetrahydroprotoberberine 
• 1429118-77-3 (S)-(6-((7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-2,3-dimethoxyphenyl)methanol 
• 1422431-47-7 (S)-6-((7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-2,3-dimethoxybenzyl acetate 
• 1422431-39-7 6-((7-(benzyloxy)-6-methoxy-3,4-dihydroisoquinolin-1-yl)methyl)-2,3-dimethoxybenzyl acetate 
• 1422431-32-0 6-(2-(4-(benzyloxy)-3-methoxyphenethylamino)-2-oxoethyl)-2,3-dimethoxybenzyl acetate 

Downstream Products

• 518-90-1 3,4-dimethoxy-phthalic acid 
• 99866-19-0 4-ethoxy-5-methoxy-phthalic acid 
• 483-14-7 tetrahydropalmatine 
• 3621-36-1 columbamine 
• 522-97-4 canadine 

Relevant articles and documents

TETRAHYDROPROTOBERBERINE COMPOUND, PREPARATION METHOD THEREFOR AND USES THEREOF, AND PHARMACEUTICAL COMPOSITION

The present invention provides a tetrahydroprotoberberine compound represented by the formula (I), enantiomers, diastereomers, racemates and mixtures thereof, and pharmaceutically acceptable salts, crystalline hydrates and solvates thereof. The invention also provides a method for preparing the compound and the use thereof in the preparation of a medicament for preventing and/or treating central nervous system diseases.

Tetrahydropalmatine derivative and preparation method and application thereof

The invention discloses a compound and a preparation method and application thereof. The compound is a compound shown in the formula I or stereisomer, geometric isomer, tautomer, nitrogen oxide, hydrate solvate, metabolite and pharmaceutically-acceptable salt or prodrug of the compound shown in the formula I. The compound is a tetrahydropalmatine derivative. The compound has the application in preparing medicine. The medicine can remarkably restrain proliferation of eucaryon tumor cells and/or treat or prevent tumors. The formula I is shown in the specification.

A divergent route to 9,10-oxygenated tetrahydroprotoberberine and 8-oxoprotoberberine alkaloids: Synthesis of (±)-isocorypalmine and oxypalmatine

A new route, which is germane to the synthesis of 9,10-oxygenated tetrahydroprotoberberines and 8-oxoprotoberberines is described. The route features the use of a diester (14) generated from reaction of dimethylmalonate with an aryl halide in the presence of n-butyllithium. The amide 17 prepared in subsequent steps is a versatile precursor for the synthesis of tetrahydroprotoberberine and 8-oxoprotoberberine scaffolds using standard high-yielding reactions. In this manner, (±)-isocorypalmine and oxypalmatine have been synthesized in 23% and 22% yields, respectively.