1,8,9-Trihydroxyanthracene - ≥98% , CAS No.1143-38-0

CAS: 1143-38-0 Cat. No.: T121104 Molecular Weight: 226.23 Beilstein Registry Number: 2054360 EC Number: 214-538-0 PubChem CID: 2202

GRADE & PURITY ≥98%

Synonyms

NSC 403736 | NSC43970 | NSC-43970 | Anthralin, Dithranol | DITHRANOL [IARC] | 1,8 Dihydroxy 9 anthrone | 1,8-Dihydroxyanthrone | cignoline | SPECTRUM1500127 | Anthralin (USP) | DITHRANOL [EP IMPURITY] | DTXSID7024538 | HMS500B03 | Prestwick_528 | NSC 4397

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Dithranol (1, 8 - dihydroxy-9-anthrone) is also called as anthralin. It is a vital topical antipsoriatic drugs. Dithranol, an athracene derivative, is a free radical generating mitochondrial poison that induces apoptosis in keratinocytes.
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.

Specifications

Synonyms

NSC 403736 | NSC43970 | NSC-43970 | Anthralin, Dithranol | DITHRANOL [IARC] | 1, 8 Dihydroxy 9 anthrone | 1, 8-Dihydroxyanthrone | cignoline | SPECTRUM1500127 | Anthralin (USP) | DITHRANOL [EP IMPURITY] | DTXSID7024538 | HMS500B03 | Prestwick_528 | NSC 4397

Specifications & Purity

≥98%

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Product Properties

• ALogP: 3.2

Names and Identifiers

• Canonical Smiles: C1C2=C(C(=CC=C2)O)C(=O)C3=C1C=CC=C3O
• IUPAC Name: 1,8-dihydroxy-10H-anthracen-9-one
• InChIKey: NUZWLKWWNNJHPT-UHFFFAOYSA-N
• INCHI: 1S/C14H10O3/c15-10-5-1-3-8-7-9-4-2-6-11(16)13(9)14(17)12(8)10/h1-6,15-16H,7H2
• Isomeric SMILES: C1C2=C(C(=CC=C2)O)C(=O)C3=C1C=CC=C3O
• WGK Germany: 3
• RTECS: CB8927000
• Alternate CAS: 480-22-8
• PubChem CID: 2202
• Molecular Weight: 226.23
• Beilstein: 2054360

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Anthracenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Anthracenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Anthracenes
• Alternative Parents: Aryl ketones 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Anthracene - Aryl ketone - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Vinylogous acid - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.
• External Descriptors: anthracenes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

HPN Tchem Serine protease hepsin (1 Activities)

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SIRT5 Tchem NAD-dependent protein deacylase sirtuin-5, mitochondrial (2 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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METAP2 Tchem Methionine aminopeptidase 2 (1512 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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KM12 (47707 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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Associated Targets(non-human)

Trypsin (394 Activities)

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Cruzipain (33337 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Plasmodium falciparum (966862 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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Genome polyprotein (620 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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ARG1 Arginase-1 (70 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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SARS-CoV-2 (38078 Activities)

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Vero C1008 (1716 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• Sensitivity: Moisture sensitive.
• Melt Point(°C): 181°C
• Molecular Weight: 226.230 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 226.063 Da
• Monoisotopic Mass: 226.063 Da
• Topological Polar Surface Area: 57.500 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 287.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zhen-Zong Bao, Zhi-Feng Chen, Si-Qi Lu, Guangzhao Wang, Zenghua Qi, Zongwei Cai.  (2021)  Effects of hydroxyl group content on adsorption and desorption of anthracene and anthrol by polyvinyl chloride microplastics.  SCIENCE OF THE TOTAL ENVIRONMENT,      [PMID:34090159] [10.1016/j.scitotenv.2021.148077]

2. Hu Ao, Li Jing, Tang Wei, Liu Ge, Zhang Haiwei, Liu Chunlan, Chen Xulin.  (2020)  Anthralin Suppresses the Proliferation of Influenza Virus by Inhibiting the Cap-Binding and Endonuclease Activity of Viral RNA Polymerase.  Frontiers in Microbiology,      [PMID:32132985] [10.3389/fmicb.2020.00178]

3. Sammar Fathy Elhabal, Nashwa Abdelaal, Saeed AS Al-Zuhairy, Mohamed Fathi Mohamed Elrefai, Mohamed Mansour Khalifa, Mohammad Ahmad Khasawneh, Ahmed Mohsen Elsaid Hamdan, Passant M Mohie, Rania A Gad, Soad L Kabil, Mohamed Kandeel El-Ashery, Bhaskara R Jasti, Nahla A Elzohairy, Nehal Elfar, Tayseer Elnawawy, Fatma E Hassan, Mohamed Ahmed El-Nabarawi.  (2024)  Revolutionizing Psoriasis Topical Treatment: Enhanced Efficacy Through Ceramide/Phospholipid Composite Cerosomes Co-Delivery of Cyclosporine and Dithranol: In-Vitro, Ex-Vivo, and in-Vivo Studies.  International Journal of Nanomedicine,      [PMID:38344440] [10.2147/IJN.S443812]