6018-40-2

Basic information

• Product Name: (+)-CORYPALMINE
• Synonyms: AKOS 238-02;(+)-CORYPALMINE;CORYPALMINE, (+)-;(-)-Tetrahydrojatrorrhizi;(13aS)-2,9,10-Trimethoxy-5,6,13,13a-tetrahydro-8H-dibenzo[a,g]quinolizine-3-ol;(S)-Corypalmine;[13aS,(-)]-5,8,13,13a-Tetrahydro-2,9,10-trimethoxy-6H-dibenzo[a,g]quinolizine-3-ol
• CAS NO: 6018-40-2
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.4
• EINECS: 200-258-5
• Product Categories: Alkaloids
• Mol File: 6018-40-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 501.2oC at 760 mmHg
• Flash Point: 256.9oC
• Appearance: /
• Density: 1.29g/cm3
• Vapor Pressure: 1.14E-10mmHg at 25°C
• Refractive Index: 1.64
• CAS DataBase Reference: (+)-CORYPALMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-CORYPALMINE(6018-40-2)
• EPA Substance Registry System: (+)-CORYPALMINE(6018-40-2)

Safety Data

• Hazardous Substances Data: 6018-40-2(Hazardous Substances Data)

Usage

General Description

(+)-CORYPALMINE is a natural alkaloid compound that has been isolated from various plant species. It has been found to exhibit a range of pharmacological properties, including anti-inflammatory, analgesic, and antioxidant activities. Studies have also shown that it may have potential neuroprotective effects and could be a promising candidate for the development of therapeutic agents for neurodegenerative diseases. Additionally, (+)-CORYPALMINE has been investigated for its potential as an anti-cancer agent, with some evidence suggesting that it may have cytotoxic effects on cancer cells. Overall, (+)-CORYPALMINE shows promising medicinal properties and is of interest for further research and potential drug development.

InChI:InChI=1/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)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

Upstream product

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• 4697-59-0 7,8-dimethoxyisochroman-3-one 
• 186581-53-3 diazomethane 
• 27313-88-8 o-Benzyloxy-(+/-)-corypalmine 
• 6681-15-8 jatrorrhizine hydrochloride 
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• 56201-87-7 8-hydroxy-7-methoxyisobenzofuranyltetrahydropyran-3-one 
• 1131-94-8 homoisovanillic acid 
• 19626-36-9 methyl 2-(3-bromo-4-methoxyphenyl)acetate 

Downstream Products

• 483-14-7 tetrahydropalmatine 
• 518-90-1 3,4-dimethoxy-phthalic acid 
• 99866-19-0 4-ethoxy-5-methoxy-phthalic acid 

Relevant articles and documents

Asymmetric total synthesis of tetrahydroprotoberberine derivatives and evaluation of their binding affinities at dopamine receptors

Cocaine addiction remains a serious challenge for clinical and medical research because there is no effective pharmacological treatment. L-THP, a natural product isolated from Corydalis yanhusuo W.T. Wang, is one of the most frequently used traditional herbs to treat drug addiction in China. Our laboratory first reported that its demethylated metabolites L-ICP, L-CD, and L-CP had high affinity at dopamine D1, D2, and D5 receptors. Here we report the chemical synthesis of these metabolites and other derivatives and their binding affinities at dopamine receptors. The synthesis of these bioactive metabolites will allow further in vivo study of their potential in treating cocaine addiction.

UNUSUAL METHYL TRANSFER IN THE BIOSYNTHESIS OF APORPHINE AND PROTOBERBERINE ALKALOIDS

(S)-Reticuline was triply-labelled with 13C and administrered to cell cultures of Peumus boldus and Berberis stolonifera, which are sources of aporphines and protoberberines, respectively.During incorporation of the labelled precursor into alkaloids of both groups, unexpected transmethylations of the methyl groups were observed by 13C NMR spectroscopy which seem to proceed via demethylation, flux of 13C through the C-1 pool, and remethylation. Key Word Index: Peumus boldus; Berberis stolonifera; Berberidaceae; cell suspension cultures; 13C NMR; reticuline; aporphines; protoberberines; alkaloids; biosynthesis

THE ABSOLUTE CONFIGURATION OF BERBERASTINE AND THALIDASTINE

Optical resolution of (+/-)-tetrahydrojatrorrhizine using (-)-O,O-di-p-toluoyl-d-tartaric acid gave rise to (+)-tetrahydrojatrorrhizine (6) of high optical purity and of known absolute configuration.Oxidation of this enantiomer with lead tetraacetate, followed by acid hydrolysis, furnished alcohols 10 and ll in a 2:1 ratio, whose relative stereochemistry was established from their nmr spectra.Iodine oxidation of the major alcohol 10 led to protoberberinium salt 14 which was found to be dextrorotatory.Since berberastine (1) and thalidastine (2) are also dextrorotatory, they must possess the same absolute configuration as 14.