518-83-2

Basic information

• Product Name: 1,3-DIHYDROXYANTHRAQUINONE
• Synonyms: 1,3-DIHYDROXYANTHRAQUINONE;PURPUROXANTHIN;xanthopurpurin;1,3-Dihydroxy-9,10-anthracenedione;2,4-Dihydroxy-9,10-anthracenedione;1,3-dihydroxy-9,10-anthraquinone;1,3-dihydroxyanthracene-9,10-dione
• CAS NO: 518-83-2
• Molecular Formula: C₁₄H₈O₄
• Molecular Weight: 240.21
• Mol File: 518-83-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 266-268℃
• Boiling Point: 514.5 ºC at 760 mmHg
• Flash Point: 279 ºC
• Appearance: /
• Density: 1.54 g/cm³
• Vapor Pressure: 3.31E-11mmHg at 25°C
• Refractive Index: 1.732
• CAS DataBase Reference: 1,3-DIHYDROXYANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIHYDROXYANTHRAQUINONE(518-83-2)
• EPA Substance Registry System: 1,3-DIHYDROXYANTHRAQUINONE(518-83-2)

Safety Data

• Hazardous Substances Data: 518-83-2(Hazardous Substances Data)

Usage

General Description

1,3-Dihydroxyanthraquinone, also known as purpurin, is a chemical compound that belongs to the anthraquinone group. It is a red pigment found in rhubarb and other plants, and it is often used as a dye in the textile industry. 1,3-Dihydroxyanthraquinone has also been studied for its potential therapeutic properties, including its ability to inhibit the growth of cancer cells. Additionally, it has been used in traditional medicine as a laxative and to treat skin diseases. 1,3-DIHYDROXYANTHRAQUINONE has a wide range of applications and potential benefits, making it an important area of research in the fields of chemistry, medicine, and industry.

InChI:InChI=1/C14H8O4/c15-7-5-10-12(11(16)6-7)14(18)9-4-2-1-3-8(9)13(10)17/h1-6,15-16H

Upstream product

• 67-56-1 methanol 
• 478-08-0 1,3-dihydroxy-2-hydroxymethyl-9,10-anthraquinone 
• 85-44-9 phthalic anhydride 
• 108-46-3 recorcinol 
• 151-10-0 1,3-Dimethoxybenzene 
• 120-12-7 anthracene 
• 476-41-5 pseudopurpurin 

Downstream Products

• 1989-42-0 1,3-dimethoxy-9,10-anthraquinone 
• 1269985-44-5 1,3-di-p-tolylanthracene-9,10-dione 
• 1338002-05-3 1-hydroxy-3-[3-(cyclohexylamino)propoxy]-9,10-anthraquinone hydrochloride 
• 1269985-57-0 1-(3-chlorophenyl)-3-p-tolylanthracene-9,10-dione 
• 1269985-56-9 3-(4-(tert-butyl)phenyl)-1-(4-methoxyphenyl)anthracene-9,10-dione 
• 1269985-55-8 4-(3-chlorophenyl)-9,10-dioxo-9,10-dihydroanthracen-2-yl trifluoromethanesulfonate 
• 1269985-54-7 4-(3,4-dimethoxyphenyl)-9,10-dioxo-9,10-dihydroanthracen-2-yl trifluoromethanesulfonate 
• 1269985-53-6 4-(4-fluorophenyl)-9,10-dioxo-9,10-dihydroanthracen-2-yl trifluoromethanesulfonate 
• 1269985-52-5 4-(4-chlorophenyl)-9,10-dioxo-9,10-dihydroanthracen-2-yl trifluoromethanesulfonate 
• 1269985-51-4 4-(3,5-dimethylphenyl)-9,10-dioxo-9,10-dihydroanthracen-2yl trifluoromethanesulfonate 
• 1269985-50-3 4-(4-methoxyphenyl)-9,10-dioxo-9,10-dihydroanthracen-2-yl trifluoromethanesulfonate 
• 1269985-49-0 1,3-bis(4-fluorophenyl)anthracene-9,10-dione 
• 1269985-48-9 1,3-bis(4-chlorophenyl)anthracene-9,10-dione 
• 1269985-47-8 1,3-bis(3,5-dimethylphenyl)anthracene-9,10-dione 

Relevant articles and documents

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

Degradation of lucidin: New insights into the fate of this natural pigment present in Dyer's madder (Rubia tinctorum L.) during the extraction of textile artefacts

The complex mixtures of colorants present in different madder species can provide significant information about which plant species or technique was used to dye the fibres of historical textile artefacts, hence, when extracting and analysing colorants from textile artefacts as much of this information as possible should be preserved. Historical textiles are most commonly extracted with 37% hydrochloric acid: methanol: water (2:1:1, v/v/v), but this solvent system hydrolyses dye glycosides and may also induce chemical reactions. One of the primary components in Dyers’ madder (Rubia tinctorum L.) is lucidin primeveroside, but it is rarely seen in artefacts, nor is the corresponding aglycon lucidin. It has been demonstrated that the hydrochloric acid method causes hydrolysis of anthraquinone glycosides to their aglycon counterpart. Herein it is demonstrated that lucidin is not stable in such acidic conditions and degrades rapidly to xanthopurpurin. This is confirmed by HPLC, LC-MS and 1H NMR, which also provide evidence of the mechanism of degradation being a retro-aldol process.

An anthraquinone scaffold for putative, two-face bim BH3 α-helix mimic

Bim BH3 peptide features an α-helix with hotspot residues on multiple faces. Compound 5 (6-bromo-2,3-dihydroxyanthracene-9,10-dione), which adopts a rigid-plan amphipathic conformation, was designed and evaluated as a scaffold to mimic two faces of Bim α-helix. It reproduced the functionalities of both D67 and I65 on two opposing helical sides. Moreover, it maintained the two-faced binding mode during further evolution. A putative BH3 α-helix mimic and nanomolar Bcl-2/Mcl-1 dual inhibitor, 6, was obtained based on the structure of 5.