Anthralin

Base Information

• Chemical Name: Anthralin
• CAS No.: 1143-38-0
• Deprecated CAS: 480-22-8
• Molecular Formula: C14H10O3
• Molecular Weight: 226.232
• Hs Code.: 29144000
• European Community (EC) Number: 214-538-0
• NSC Number: 755873,629313,43970
• UNII: U8CJK0JH5M
• DSSTox Substance ID: DTXSID7024538
• Nikkaji Number: J5.224H
• Wikipedia: Dithranol
• Wikidata: Q419397
• NCI Thesaurus Code: C28827
• Pharos Ligand ID: 1U4RRZQC5QZB
• Metabolomics Workbench ID: 55605
• ChEMBL ID: CHEMBL46469
• Mol file: 1143-38-0.mol

Synonyms:1,8 Dihydroxy 9 anthrone;1,8,9-Anthracenetriol;1,8-Dihydroxy-9(10H)-anthracenone;1,8-Dihydroxy-9-anthrone;Anthraforte;Anthralin;Anthranol;Cignolin;Cygnoline;Dihydroxyanthranol;Dithranol;Dithrocream;Ditranol FNA;FNA, Ditranol;Lasan;Micanol;Psoradrate;Psoricrème

Chemical Property of Anthralin

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Vapor Pressure: 5.23E-09mmHg at 25°C
• Melting Point: 178-181 °C(lit.)
• Refractive Index: 1.837
• Boiling Point: 464.1 °C at 760 mmHg
• PKA: 7.16±0.20(Predicted)
• Flash Point: 248.6 °C
• PSA: 57.53000
• Density: 1.419 g/cm³
• LogP: 2.23300
• 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.
• Water Solubility.: Insoluble in water. Soluble in acetic acid, chloroform (20 mg/mL), acetone, benzene, solutions of alkali hydroxides, fixed oil.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 226.062994177
• Heavy Atom Count: 17
• Complexity: 287

Purity/Quality:

99% ^*data from raw suppliers

Anthralin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,T
• Hazard Codes: Xi,T
• Statements: 36/37/38-45
• Safety Statements: 26-53-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C(=CC=C2)O)C(=O)C3=C1C=CC=C3O
• Recent EU Clinical Trials: The induction of apoptosis by anti-psoriatic treatments
• Description: Anthralin is an anthrone inhibitor of keratinocyte proliferation and a modulator of differentiation. It increases apoptosis and inhibits proliferation of normal human keratinocytes (NHKs) when used at a concentration of 2.5 μM. It also decreases the mitochondrial membrane potential, increases cytochrome c release, and induces perinuclear mitochondrial clustering in NHKs when used at a concentration of 5 μM. 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-17A- and IL-22-stimulated NHKs. It also inhibits leukotriene B4 (LTB4; ) production, stimulated by the calcium ionophore A23187 , from human neutrophils (IC50 = 7 μM). Topical anthralin (0.1%) induces hair regrowth in a Dundee experimental bald rat (DEBR) model of alopecia areata.
• Uses: Dithranol, a potential anti-psoriasis medication, may be used to study its safety, efficacy, metabolism and pharmacological profile. Dithranol may be used to study is physicochemical properties, as a reference compound and to develop effective drug delivery vehicles. Dithranol 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.

Technology Process of Anthralin

There total 17 articles about Anthralin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.7%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) → 1,8-dihydroxy-9(10H)-anthracenone (1143-38-0)

Guidance literature:

DOI:10.1002/ardp.19843170206

Reference yield:

10-phenylthio-1,8-dihydroxy-9-anthrone (107401-55-8) → 1,8-dihydroxy-9(10H)-anthracenone (1143-38-0) + 1,8,1',8'-tetrahydroxy-10,10'-bianthrone (31991-54-5) + thiophenol (108-98-5) + diphenyldisulfane (882-33-7) + 1,8-Dihydroxy-10,10-bis-phenylsulfanyl-10H-anthracen-9-one + 4,5,4',5'-Tetrahydroxy-9-phenylsulfanyl-9H,9'H-[9,9']bianthracenyl-10,10'-dione

Guidance literature:

at 150 ℃; for 0.5h; Product distribution; various times;

DOI:10.1002/ardp.19943271013

Reference yield:

tungsten powder + H2BAQ + palladium (Pd) metal + platinum (Pt) metal + t-butyl anthrahydroquinone + t-butyl anthraquinone + anthracen-9(10H)-one (90-44-8) → 1,8-dihydroxy-9(10H)-anthracenone (1143-38-0)

Guidance literature:

With hydrogen; Pd; Pt; In 1-methyl-pyrrolidin-2-one;

upstream raw materials:

1,8-dimethoxy-9,10-anthracenedione

1,4-dihydroxy-9,10-anthracenedione

1,8-dihydroxy-9,10-anthracenedione

10-phenylthio-1,8-dihydroxy-9-anthrone

Downstream raw materials:

8,9-dihydroxy-3,4-dihydro-2H-anthracen-1-one

1,8,9-triacetyloxyanthracene

1,8-Dihydroxy-10-(3-(4-methoxyphenyl)-1-oxopropyl)-9(10H)-anthracenone

1,8-Dihydroxy-10-(methoxy-phenyl-methyl)-10H-anthracen-9-one

Refernces

• 1、 Loh, Charles C. J.,Fang, Xiang,Peters, Brendan,Lautens, Mark. "Benzylic Functionalization of Anthrones via the Asymmetric Ring Opening of Oxabicycles Utilizing a Fourth-Generation Rhodium Catalytic System". . p. 13883 - 13887. Retrieved 2015.
• 2、 Jalab, Murhaf,Critchley, Megan E.,Taylor, Charlotte M.,Lawrence, Clare L.,Smith, Robert B.. "1,8-Substituted anthraquinones, anthrones and bianthrones as potential non-azole leads against fungal infections". . . Retrieved 2019.
• 3、 Tanner, Philipp,Maier, Gerhard,Schlüter, A. Dieter. "Synthesis of a Monomer for Two-Dimensional Polymerization under Technically Feasible Conditions". . . Retrieved 2018.
• 4、 Rosenberg,Rostgaard,Liao,Madsen,Martinez,Vosch,Laursen. "Design, synthesis, and time-gated cell imaging of carbon-bridged triangulenium dyes with long fluorescence lifetime and red emission". . p. 3122 - 3130. Retrieved 2018.