31991-54-5

Basic information

• Product Name: 1,8,1',8'-tetrahydroxybisanthrone
• Synonyms: 1,8,1',8'-tetrahydroxybisanthrone
• CAS NO: 31991-54-5
• Molecular Formula: C₂₈H₁₈O₆
• Molecular Weight: 450.43892
• Mol File: 31991-54-5.mol

Chemical Properties

• Melting Point: 210-213 °C
• Boiling Point: 631°Cat760mmHg
• Flash Point: 349.4°C
• Appearance: /
• Density: 1.539g/cm³
• PKA: 6.77±0.40(Predicted)
• CAS DataBase Reference: 1,8,1',8'-tetrahydroxybisanthrone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8,1',8'-tetrahydroxybisanthrone(31991-54-5)
• EPA Substance Registry System: 1,8,1',8'-tetrahydroxybisanthrone(31991-54-5)

Safety Data

• Hazardous Substances Data: 31991-54-5(Hazardous Substances Data)

Usage

Chemical classification

Anthraquinone derivative

Use

Red dye in the textile industry

Physical appearance

Dark red crystalline powder

Solubility

Insoluble in water, soluble in organic solvents

Pharmacological properties

Antioxidant and antitumor effects

Potential medical applications

Treatment of inflammation and cancer

Safety precautions

Handle with caution due to potential toxicity

Upstream product

• 1143-38-0 1,8-dihydroxy-9(10H)-anthracenone 
• 107401-55-8 10-phenylthio-1,8-dihydroxy-9-anthrone 

Downstream Products

• 88810-45-1 C₃₂H₃₈NO₄ 
• 88810-47-3 C₃₂H₃₆⁽²⁾H₂NO₄ 

Relevant articles and documents

Dithranol reaction with nitroxide radicals in DMSO, a HPLC study

Dithranol (1,8-dihydroxy-9-anthrone), an efficient drug for the topical treatment of psoriasis undergoes a complex chemical transformation after topical application. An absorption phase HPLC method has been developed and validated to follow the appearance of its oxidative products in a DMSO solution. In DMSO solution dithranol, chrysazin, and biantrone were monitored simultaneously by HPLC during autooxidation process, as well as in the presence of nitroxide radicals which increase the reaction rate. The kinetics of the very early stage of dithranol transformation is presented for the first time and discussed. Two unknown dithranol-derived intermediates were found and partially characterised.

Electron-impact induced and thermal decomposition of dithranol derivatives, I: Thermolysis of 10-phenylthio-dithranol in the mass spectrometer

Dithranol (anthralin; 1,8-dihydroxy-9-anthrone) and its derivatives bearing a variety of substituents in the 10-position are of actual interest in research on psoriasis. In connection herewith 10-alkylthio- and 10-arylthio-1,8-dihydroxy-9(10H)-anthracenones were synthetized and used for antipsoriatic activity.

Oxygenation of Dithranol by complexes of transition elements

The oxygen activation in the dark by complexes of transition metals in the presence of the antipsoriatic compound dithranol (1a) is described.With the system CuCl/O2 an electron transfer oxygenation occurs, which simulates a 1O2-reaction, without an attack of 1O2.In the presence of Co-Salen/O2 the mechanism depends on the solvent and substrate, as already shown in the naphthalene-series.In methylenchloride dantrone (2), the radical product bisanthrone 3 and 1,8,10-trihydroxy-9-anthrone (4) are identified.The mechanistic particularity of this reaction in methylenchloride is discussed.

GENERATION AND ROLE OF SUPEROXIDE ION IN THE AUTOXIDATION OF 1,8-DIHYDROXY-9-ANTHRONE

The autoxidation of anthralin (1,8-dihydroxy-9-anthrone, 1) at various pH values in Hepes buffer-acetonitrile is reported.The relative importance of the two main oxidation routes of anthralin, i.e. conversion to 1,8-dihydroxy-9,10-anthraquinone, 2, and to 1,8,1',8'-tetrahydroxy-10,10'-bianthrone, 3, is shown to be markedly dependent on pH.In particular, the product ratio of 2/3 is very low at pH 6 (0.05) but increases at higher pH (1.7 at pH 10.5).The reaction is accompanied by a significant production of superoxide at pH > 7.Addition of superoxide dismutase specifically inhibits the formation of 2.These findings are explained by assuming a direct interaction of the intermediate anthronyl radical 4 with superoxide, which ultimately leads to the quinone 2 at alkaline pH.

Studies on the oxidation behaviour of dithranol

When Dithranol is oxidized in a weakly alkaline buffer by air oxygen one has to discuss two different oxidative pathways. Under homogeneous conditions (dithranol dissolved) the only oxidation product is dithranol-dimer (and subsequently dithranol-brown) whereas under heterogeneous conditions (dithranol suspended) mainly chrysazine (dantron) is produced, which does not alter under the chosen conditions. These circumstances may play an important part in the dithranol therapy of psoriasis.