37687-34-6

Basic information

• Product Name: 6-Acetonyldihydrosanguinarine
• Synonyms: 6-Acetonyldihydrosanguinarine;(S)-(+)-6-Acetonyldihydrosanguinarine;6-Acetonyl-5,6-dihydrosanguinarine;8-Acetonyldihydrosanguinarine
• CAS NO: 37687-34-6
• Molecular Formula: C23H19NO5
• Molecular Weight: 389.40066
• Mol File: 37687-34-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 597.3°C at 760 mmHg
• Flash Point: 315°C
• Appearance: /
• Density: 1.367g/cm³
• Vapor Pressure: 3.15E-14mmHg at 25°C
• Refractive Index: 1.668
• PKA: 1.67±0.40(Predicted)
• CAS DataBase Reference: 6-Acetonyldihydrosanguinarine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Acetonyldihydrosanguinarine(37687-34-6)
• EPA Substance Registry System: 6-Acetonyldihydrosanguinarine(37687-34-6)

Safety Data

• Hazardous Substances Data: 37687-34-6(Hazardous Substances Data)

Usage

General Description

6-Acetonyldihydrosanguinarine is a chemical compound that belongs to the class of alkaloids, which are naturally occurring organic compounds that have basic properties and contain nitrogen atoms. This particular compound is a derivative of dihydrosanguinarine, and it features an acetonyl group attached to the molecule. It is commonly found in certain plant species, such as Bloodroot (Sanguinaria canadensis) and Macleaya cordata. This chemical compound has been studied for its potential pharmacological properties, including its antimicrobial, anti-inflammatory, and anticancer activities. Its structure and properties make it a subject of interest in the field of medicinal chemistry and natural product research.

InChI:InChI=1/C23H19NO5/c1-12(25)7-17-21-14(5-6-18-23(21)29-11-26-18)15-4-3-13-8-19-20(28-10-27-19)9-16(13)22(15)24(17)2/h3-6,8-9,17H,7,10-11H2,1-2H3

Upstream product

• 67-64-1 acetone 
• 2447-54-3 Sanguinarine 
• 5578-73-4 sanguinarine chloride 

Relevant articles and documents

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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.