28342-31-6

Basic information

• Product Name: Ethoxysanguinarine
• Synonyms: Ethoxysanguinarine;($$+/-$$)-Sanguinarine pseudoethanolate;14-Ethoxy-13,14-dihydrosanguinarine;14-Ethoxy-13-Methyl-13,14-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridine;14-Ethoxy-13,14-dihydrosanguinarine (±)-Sanguinarine pseudoethanolate;6-Ethoxysanguinarine;6-Ethoxydihydrosanguinarine
• CAS NO: 28342-31-6
• Molecular Formula: C22H18NO5
• Molecular Weight: 376.386
• Product Categories: reagent;standard substance
• Mol File: 28342-31-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 210-212℃ (ethanol )
• Boiling Point: 563.7oC at 760 mmHg
• Flash Point: 169oC
• Appearance: /
• Density: 1.45±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 9.92E-13mmHg at 25°C
• Refractive Index: 1.724
• CAS DataBase Reference: Ethoxysanguinarine(CAS DataBase Reference)
• NIST Chemistry Reference: Ethoxysanguinarine(28342-31-6)
• EPA Substance Registry System: Ethoxysanguinarine(28342-31-6)

Safety Data

• Hazardous Substances Data: 28342-31-6(Hazardous Substances Data)

Usage

General Description

Ethoxysanguinarine is a chemical compound derived from the plant Sanguinaria canadensis, commonly known as bloodroot. It belongs to the class of isoquinoline alkaloids and is characterized by its antifungal and antibacterial properties. Ethoxysanguinarine has been studied for its potential use in therapeutic applications, particularly in the treatment of cancer due to its cytotoxicity against cancer cells and ability to inhibit cell proliferation. Research has also shown that it has neuroprotective and anti-inflammatory properties, making it a compound of interest in the development of new drugs for the treatment of neurodegenerative diseases and inflammatory conditions. Additionally, ethoxysanguinarine has been investigated for its potential as a natural herbicide and insecticide due to its pesticidal activities.

InChI:InChI=1/C22H19NO5/c1-3-24-22-19-13(6-7-16-21(19)28-11-25-16)14-5-4-12-8-17-18(27-10-26-17)9-15(12)20(14)23(22)2/h4-9,22H,3,10-11H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 4070-41-1 8-hydroxydihydosanguinarine 
• 5578-73-4 sanguinarine chloride 
• 141-52-6 sodium ethanolate 
• 2447-54-3 Sanguinarine 

Downstream Products

• 28342-28-1 Methoxybocconine 
• 28342-26-9 dihydrochelirubine 

Relevant articles and documents

Some structural relationships among cytotoxic and antitumor benzophenanthridine alkaloid derivatives

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In vitro antifungal activity of sanguinarine and chelerythrine derivatives against phytopathogenic fungi

In order to understand the antifungal activity of some derivatives of sanguinarine (S) and chelerythrine (C) and their structure-activity relationships, sixteen derivatives of S and C were prepared and evaluated for in vitro antifungal activity against seven phytopathogenic fungi by the mycelial growth rate method. The results showed that S, C and their 6-alkoxy dihydro derivatives S1-S4, C1-C4 and 6-cyanodihydro derivatives S5, C5 showed significant antifungal activity at 100 μg/mL against all the tested fungi. For most tested fungi, the median effective concentrations of S, S1, C and C1 were in a range of 14-50 μg/mL. The structure-activity relationship showed that the C=N+ moiety was the determinant for the antifungal activity of S and C. S1-S5 and C 1-C5 could be considered as the precursors of S and C, respectively. Thus, the present results strongly suggested that S and C or their derivatives S1-S5 and C1-C5 should be considered as good lead compounds or model molecules to develop new anti-phytopathogenic fungal agents.