25395-11-3

Basic information

• Product Name: Triacetyl Aloe-emodin (Impurity A)
• Synonyms: 1,8-Bis(acetyloxy)-3-[(acetyloxy)methyl]-9,10-anthracenedione;1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone Triacetate;Aloe-emodin Impurity A;Triacetyl Aloe-emodin (Impurity A);1,8-Bis(acetyloxy)-3-[(acetyloxy)Methyl]-;Triacetyl aloe-eModin;Diacerein IMpurity H;Diacerein EP Impurity H
• CAS NO: 25395-11-3
• Molecular Formula: C₂₁H₁₆O₈
• Molecular Weight: 396.35
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics
• Mol File: 25395-11-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 175-177℃
• Boiling Point: 579.7°C at 760 mmHg
• Flash Point: 254.1°C
• Appearance: /
• Density: 1.380
• Vapor Pressure: 1.96E-13mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: Triacetyl Aloe-emodin (Impurity A)(CAS DataBase Reference)
• NIST Chemistry Reference: Triacetyl Aloe-emodin (Impurity A)(25395-11-3)
• EPA Substance Registry System: Triacetyl Aloe-emodin (Impurity A)(25395-11-3)

Safety Data

• Hazardous Substances Data: 25395-11-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Different sources of media describe the Uses of 25395-11-3 differently. You can refer to the following data:
1. Aloe-emodin impurity A & Diacerein EP Impurity H.
2. Aloe-emodin impurity A

InChI:InChI=1/C21H16O8/c1-10(22)27-9-13-7-15-19(17(8-13)29-12(3)24)21(26)18-14(20(15)25)5-4-6-16(18)28-11(2)23/h4-8H,9H2,1-3H3

Synthetic route

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + acetic anhydride (108-24-7) → triacetyl aloe-emodin (25395-11-3)

Conditions	Yield
With pyridine at 50℃; for 24h;	76%
With sodium acetate

1,8-diacetoxy-3-methyl-anthraquinone (18713-45-6) → triacetyl aloe-emodin (25395-11-3)

Conditions	Yield
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide anschliessende Umsetzung mit Silberacetat in Acetanhydrid;

triacetyl aloe-emodin (25395-11-3) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With sulfuric acid

triacetyl aloe-emodin (25395-11-3) → diacetylrhein (13739-02-1)

Upstream product

• 18713-45-6 1,8-diacetoxy-3-methyl-anthraquinone 
• 481-72-1 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione 
• 108-24-7 acetic anhydride 

Downstream Products

• 481-72-1 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione 
• 13739-02-1 diacetylrhein 

Relevant articles and documents

Synthesis, biological evaluation and molecular modeling of aloe-emodin derivatives as new acetylcholinesterase inhibitors

A series of aloe-emodin derivatives were designed, synthesized and evaluated as acetylcholinesterase inhibitors. Most of the new prepared compounds showed remarkable acetylcholinesterase inhibitory activities. Among them, the compound 1-((4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl) methyl) pyridin-1-ium chloride (C3) which has a pyridinium substituent possessed the best inhibitory activity of acetylcholinesterase (IC50 = 0.09 μM). The docking study performed with AUTODOCK demonstrated that C3 could interact with the catalytic active site (CAS) and the peripheral anionic site (PAS) of acetylcholinesterase.