1143-38-0

Basic information

• Product Name: ANTHRALIN
• Synonyms: DITHRANOL;DITHRANOL, ANTHRALIN;ANTHRALIN;1,8-DIHYDROXY-10H-ANTHRACEN-9-ONE;1,8-DIHYDROXY-9(10H)-ANTHRACENONE;1,8-DIHYDROXYANTHRONE;1,8,9-ANTHRACENETRIOL;1,8-dihydroxy-9(10h)-anthracenon
• CAS NO: 1143-38-0
• Molecular Formula: C₁₄H₁₀O₃
• Molecular Weight: 226.23
• EINECS: 214-538-0
• Product Categories: Aromatic Phenols;Intermediates & Fine Chemicals;Pharmaceuticals;ANTRADERM;Skin drugs, treatment of psoriasis;API
• Mol File: 1143-38-0.mol

Chemical Properties

• Melting Point: 178-181 °C(lit.)
• Boiling Point: 464.1 °C at 760 mmHg
• Flash Point: 248.6 °C
• Appearance: yellow crystalline solid
• Density: 1.419 g/cm³
• Vapor Pressure: 5.23E-09mmHg at 25°C
• Refractive Index: 1.837
• Storage Temp.: 2-8°C
• Solubility: Practically insoluble in water, soluble in methylene chloride, sparingly soluble in acetone, slightly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides.
• PKA: 7.16±0.20(Predicted)
• Water Solubility: Insoluble in water. Soluble in acetic acid, chloroform (20 mg/mL), acetone, benzene, solutions of alkali hydroxides, fixed oil.
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,684
• BRN: 2054360
• CAS DataBase Reference: ANTHRALIN(CAS DataBase Reference)
• NIST Chemistry Reference: ANTHRALIN(1143-38-0)
• EPA Substance Registry System: ANTHRALIN(1143-38-0)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-45
• Safety Statements: 26-53-45
• WGK Germany: 3
• RTECS: CB8927000
• Hazardous Substances Data: 1143-38-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Anthralin is used as a treatment for psoriasis, a chronic skin condition characterized by the rapid growth and shedding of skin cells. It works by inhibiting the proliferation of normal human keratinocytes and modulating their differentiation. At a concentration of 2.5 μM, anthralin increases apoptosis and inhibits proliferation of normal human keratinocytes. It also decreases the mitochondrial membrane potential, increases cytochrome c release, and induces perinuclear mitochondrial clustering in these cells when used at a concentration of 5 μM.
Additionally, anthralin (0.25 μM) decreases the expression of β-defensin-2 and S100 calcium-binding protein A9 (S100A9) and increases the expression of IL-6 and IL-8 in IL-17Aand IL-22-stimulated normal human keratinocytes. It also inhibits leukotriene B4 (LTB4) production, stimulated by the calcium ionophore A23187, from human neutrophils (IC50 = 7 μM).
Used in Dermatology:
Topical anthralin (0.1%) has been shown to induce hair regrowth in a Dundee experimental bald rat (DEBR) model of alopecia areata, a condition characterized by hair loss due to autoimmune attack on hair follicles.
Used in Research:
Anthralin may be used in research to study its safety, efficacy, metabolism, and pharmacological profile. It may also be used to study its physicochemical properties, as a reference compound, and to develop effective drug delivery vehicles. Furthermore, anthralin may be used as a matrix for matrix-assisted laser desorption/ionization imaging on a Fourier transform ion cyclotron resonance mass spectrometer.

Indications

Anthralin (Anthra-Derm) is a potent reducing agent whose mechanism of action is unknown. It is approved for the treatment of psoriasis and also may be helpful in alopecia areata. The major toxicities are discoloration of skin, hair, and nails and irritant dermatitis.

Air & Water Reactions

Unstable in air when in alkaline solution. Insoluble in water.

Reactivity Profile

ANTHRALIN reacts as a weak acid. Soluble in aqueous bases. May react with strong oxidizing agents. May be sensitive to light and moisture .

Hazard

Very irritating. Do not use on scalp or near eyes.

Fire Hazard

Flash point data are not available for ANTHRALIN; however, ANTHRALIN is probably combustible.

Side effects

Anthralin's side effects include pruritus, erythema, scaling, folliculitis, and lymphadenopathy. Staining of skin and clothes can also be an issue.

InChI:InChI=1/C14H10O3/c15-10-5-1-3-8-7-9-4-2-6-11(16)13(9)14(17)12(8)10/h1-7,15-17H

Upstream product

• 6407-55-2 1,8-dimethoxy-9,10-anthracenedione 
• 90-44-8 anthracen-9(10H)-one 
• 89646-23-1 2-(2-Hydroxybenzoyl)-3-nitro-benzoesaeure 
• 89646-25-3 3-Hydroxy-2-(2-hydroxybenzoyl)-benzoesaeure 
• 89646-24-2 3-Amino-2-(2-hydroxybenzoyl)-benzoesaeure 
• 641-70-3 3-nitrophthalic acid anhydride 
• 176505-06-9 1,8-Dimethoxy-9-hydroxyanthracene 
• 117-10-2 1,8-dihydroxy-9,10-anthracenedione 
• 108-90-7 chlorobenzene 
• 69595-66-0 1,8-bis(benzyloxy)-9,10-anthracenedione 
• 176505-14-9 10-benzoyl-1,8-dimethoxy-9-hydroxyanthracene 
• 3360-93-8 10-acetyl-1,8,9-triacetoxy anthracene 
• 107401-55-8 10-phenylthio-1,8-dihydroxy-9-anthrone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 

Downstream Products

• 10183-94-5 8,9-dihydroxy-3,4-dihydro-2H-anthracen-1-one 
• 16203-97-7 1,8,9-triacetyloxyanthracene 
• 104608-82-4 1,8-dihydroxy-10-ethyl-9(10H)-anthracenone 
• 151562-48-0 1,8-Dihydroxy-10-(1-oxo-3-phenylpropyl)-9(10H)-anthracenone 
• 2891-30-7 10-bromo-1,8-dihydroxy-9(10H)-anthracenone 
• 75464-11-8 1,8-dihydroxy-10-(1'-oxobutyl)-9(10H)-anthracenone 
• 102768-28-5 1,8-dihydroxy-10-isobutyrylanthrone 
• 3022-61-5 1,8-dihydroxy-10-acetylanthrone 
• 64817-78-3 10-Myristoyl-anthralin 
• 64817-77-2 1,8-Dihydroxy-4-anthron-dimyristat 
• 151562-56-0 1,8-dihydroxy-10-(1-oxo-5-phenylpentyl)-9(10H)-anthracenone 
• 151562-43-5 1,8-dihydroxy-10-<2-(4-methoxyphenyl)-1-oxoethyl>-9(10H)-anthracenone 
• 151562-41-3 1,8-dihydroxy-10-(1-oxo-2-phenylethy)-9(10H)-anthracenone 
• 162750-58-5 (E)-1,8-dihydroxy-10-(1-oxo-3-phenyl-2-propenyl)-9(10H)-anthracenone 

Relevant articles and documents

Benzylic Functionalization of Anthrones via the Asymmetric Ring Opening of Oxabicycles Utilizing a Fourth-Generation Rhodium Catalytic System

While anthrones exist as privileged scaffolds in bioactive molecules, the enantioselective functionalization of anthrones is surprisingly scarce in the literature, with no asymmetric transition metal catalyzed example to date. Herein, we report the first asymmetric transition metal catalyzed benzylic functionalization of anthrones through the rhodium(I) catalyzed desymmetrization of oxabicycles. As previously developed rhodium(I) systems were found to be unsuitable for this substrate, a new robust fourth-generation [Rh(cod)OH]2 based catalytic system was developed to address synthetic challenges in this protocol.

Syntheses of anthraeenones. 1. Sodium dithionite reduction of peri-substituted anthracenediones

The reaction of peri-substituted anthracenediones with sodium dithionite in dimethylformamide and water has been investigated. The system selectively reduces the carbonyl group flanked by the peri substituents of the anthracenediones to give the corresponding 4,5-disubstituted 9(10H)-anthracenones and thus provides a route to anthracenones which are otherwise difficult to obtain. Many functional groups can be tolerated, the reaction is compatible with the presence of peri alkoxy groups and unsaturated side chains of the starting anthracenediones, and the reduction does not go beyond the anthracenone stage. However, the formation of anthracenones depends on the nature of the peri substituents. No products were obtained from the 1,8-dimethyl-substituted anthracene-dione and the parent compound with no substituents.

1,8-Substituted anthraquinones, anthrones and bianthrones as potential non-azole leads against fungal infections

The synthesis of a variety of 1,8-substituted anthraquinones, anthrones and bianthrones and their potential as antifungal agents is evaluated. Preliminary screening against Schizosaccharomyces pombe (S. pombe), a fission yeast, and Saccharomyces cerevisiae (S. cerevisiae), a budding yeast, is reported. Both these yeast species demonstrate close homologue to a number of pathogenic fungi.

Synthesis of a Monomer for Two-Dimensional Polymerization under Technically Feasible Conditions

The synthesis of a promising 2D polymer uses the double decker rotor-shaped monomer 1, containing three anthracene moieties. To accelerate the development of the field of 2D polymers, this monomer was selected for scale-up that would allow its synthesis to be performed on the kg scale under technical conditions. This goal was achieved in collaboration with Polymaterials AG, Kaufbeuren, Germany. Not only was the synthetic route shortened, but each and every aspect of the remaining steps was streamlined so as to render them applicable to technical conditions. This involved the entire sequence to be adapted to metal instead of glass reactors and to a number of safety and toxicity concerns. Additionally, not only the utilization of the reactors had to meet strict efficiency requirements, but also the work-up procedures had to be facile. The whole sequence was then tested for feasibility under realistic conditions at Polymaterials AG. While this test afforded 130?g of monomer 1, it has the clear potential for the kg scale, supposed the safety equipment for the hydrogen evolution for the conversion of compound 2a?–?3 is available.

Straightforward Access to Anthrone Functionalized Benzylic Amines via Organocatalytic 1,2-Addition of Anthrones to Imines at Ambient Temperature

Activation of anthrone via benzylic deprotonation in the presence of triethylamine paves the way for the 1,2-addition reaction with imines to provide the desired functionalized anthrones in good to excellent yields under mild and operationally simple reaction conditions with a broad range of substrate scopes without using any external additives or toxic stoichiometric reagents.

Design, synthesis, and time-gated cell imaging of carbon-bridged triangulenium dyes with long fluorescence lifetime and red emission

Time-resolved fluorescence offers many advantages over normal steady-state detection and becomes increasingly important in bioimaging. However, only very few fluorophores with emission in the visible range and fluorescence lifetimes above 5 ns are available. In this work, we prepare a series of new aza/oxa-triangulenium dyes where one of the usual oxa or aza bridges is replaced by an isopropyl bridge. This leads to a significant redshift of fluorescence with only moderate reductions of quantum yields and a unique long fluorescence lifetime. The fluorescence of the isopropyl bridged diazatriangulenium derivative CDATA+ is red-shifted by 50 nm (1400 cm-1) as compared to the oxygen-bridged DAOTA+ chromophore and has intense emission in the red region (600-700 nm) with a quantum yield of 61%, and a fluorescence lifetime of 15.8 ns in apolar solution. When the CDATA+ dye is used as cell stain, high photostability and efficient time-gated cell imaging is demonstrated.

10-α-aminoacyl-9(10H)-anthracenones: Inhibition of 12(S)-HETE biosynthesis and HaCaT cell growth

1,8-Dihydroxy-9(10H)-anthracenones with a 10-α-aminoacyl group were synthesized using either a mixed-anhydride coupling method or Boc-protected oxazotidinediones. The novel anthracenones were evaluated as inhibitors of the biosynthesis of 12(S)-hydroxyeicosatetraenoic acid (12(S)-HETE) in epidermal homogenate of mice and for inhibition of the growth of HaCaT keratinocytes. These cells were also tested for their susceptibility for the action of the most potent members of this series on plasma membrane integrity, in order to confirm that inhibition of cell growth is not a result of membrane damage induced by prooxidants released from anthracenones. Hydroxyl-radical generation as measure of the prooxidant potential of the compounds was determined by deoxyribose degradation. The most potent analogues of this series were equally potent as anthralin against 12(S)-HETE biosynthesis and keratinocyte proliferation, while oxygen-radical generation and the resulting damage to cell membrane was strongly reduced as compared to the antipsoriatic drug.

Method for treating psoriasis using selected phosphorylase kinase inhibitor and additional compounds

An improved method of treating psoriasis involves controlling the enhanced proliferation and terminal differentiation of psoriatic epidermis through the activity of epidermal phosphorylase kinase. In general, the method involves contacting psoriatic epidermal cells with a combination of substances affecting the activity of phosphorylase kinase. The combination can be: (1) a calmodulin inhibitor together with a stimulator of cAMP-dependent protein kinase II, (2) a calmodulin inhibitor together with a calcium channel blocker; (3) a stimulator of cAMP-dependent protein kinase II together with a calcium channel blocker; or (4) a calmodulin inhibitor together with a calcium channel blocker and a stimulator of cAMP-dependent protein kinase II. Alternatively, a selective phosphorylase kinase inhibitor such as curcumin can be administered, alone or with an agent such as vitamin D 3 or an analogue thereof, etretinate, diltiazem, or anthralin. The invention also includes pharmaceutical compositions.

Syntheses of anthracenones. 3. Revised preparative route to 10-Benzoyl-1,8-dihydroxy-9(10H)-anthracenones

The acylation of anthralin (1,8-dihydroxy-9(10H)-anthracenone) with acetylsalicylic acid chloride in toluene and collidine was found to give the O-acylated product, rather than 10-(acetylsalicyl)-anthralin. A procedure is described for benzoylation of anthralin in the 10-position which involves reaction of 1,8-diacetoxy-9(10H)-anthracenone with benzoyl chloride and sodium hydride in THF followed by hydrolysis of an intermediate enol ester. Furthermore, when benzoyl chloride and DMF were used for the acylation of anthralin, a Vilsmeier-type reaction was observed leading to a novel enamine derivative of anthralin which was hydrolyzed or benzoylated to an enol or enol ester, respectively.