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117-10-2,MFCD00001211
Catalog No.:AA000DF4

117-10-2 | 9,10-Anthracenedione, 1,8-dihydroxy-

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA000DF4
Chemical Name:
9,10-Anthracenedione, 1,8-dihydroxy-
CAS Number:
117-10-2
Molecular Formula:
C14H8O4
Molecular Weight:
240.2109
MDL Number:
MFCD00001211
SMILES:
Oc1cccc2c1C(=O)c1c(C2=O)cccc1O
UN Number:
2811
Properties
Computed Properties
 
Complexity:
346  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
XLogP3:
3.2  

Downstream Synthesis Route

[1]SyntheticCommunications,2010,vol.40,p.3501-3505

[2]Chemicalandpharmaceuticalbulletin,1958,vol.6,p.397,400

[1]Schrobsdorff[ChemischeBerichte,1902,vol.35,p.2930]

[1]ArchivderPharmazie,1984,vol.317,p.120-126

[2]ChemicalScience,2018,vol.9,p.3122-3130

[3]MonatsheftefurChemie,1992,vol.123,p.277-284

[4]HelveticaChimicaActa,2018,vol.101

[5]Chemistry-AEuropeanJournal,2015,vol.21,p.13883-13887

[6]BulletinoftheChemicalSocietyofJapan,1985,vol.58,p.2577-2580

[7]ChemischeBerichte,1938,vol.71,p.172,178

[8]Tetrahedron,1966,vol.22,p.2761-2783

[9]JournalofOrganicChemistry,1996,vol.61,p.2853-2856

[10]BioorganicChemistry,2019,vol.91

[1]JournalofOrganicChemistry,2005,vol.70,p.6863-6869

[2]Patent:US2841596,1953,

[3]BulletindelaSocieteChimiquedeFrance,1956,vol.4,p.303,308

[4]JournaloftheAmericanChemicalSociety,1953,vol.75,p.5455,5474

[1]Tetrahedron,2004,vol.60,p.3523-3531

[2]Synthesis,2012,vol.44,p.805-809

[3]JournaloftheAmericanChemicalSociety,2019,vol.141,p.18152-18159

[4]JournaloftheAmericanChemicalSociety,2005,vol.127,p.4354-4371

[5]TetrahedronLetters,1996,vol.37,p.6089-6092

[6]ChemischeBerichte,1986,vol.119,p.1016-1038

[7]BulletindelaSocieteChimiquedeFrance,1942,vol.<5>9,p.171,176

[8]ArchivderPharmazie,1996,vol.329,p.262-266

[9]Tetrahedron,1996,vol.52,p.13623-13640

[10]JournaloftheAmericanChemicalSociety,1999,vol.121,p.10644-10645

[11]Synthesis,2003,p.2464-2466

[12]EuropeanJournalofMedicinalChemistry,2010,vol.45,p.3354-3364

Literature

Title: Comparative developmental toxicity of environmentally relevant oxygenated PAHs.

Journal: Toxicology and applied pharmacology 20130901

Title: Danthron triggers ROS and mitochondria-mediated apoptotic death in C6 rat glioma cells through caspase cascades, apoptosis-inducing factor and endonuclease G multiple signaling.

Journal: Neurochemical research 20120801

Title: Albopunctatone, an antiplasmodial anthrone-anthraquinone from the Australian ascidian Didemnum albopunctatum.

Journal: Journal of natural products 20120622

Title: Colorimetric and fluorescence sensing of Cu2+ in water using 1,8-dihydroxyanthraquinone-β-cyclodextrin complex with the assistance of ammonia.

Journal: Talanta 20120530

Title: Toxicology study of senna (CAS No. 8013-11-4) in C57BL/6NTAC Mice and toxicology and carcinogenesis study of senna in genetically modified C3B6.129F1/Tac-Trp53tm1Brd haploinsufficient mice (Feed Studies).

Journal: National Toxicology Program genetically modified model report 20120401

Title: DNA-binding, DNA cleavage and cytotoxicity studies of two anthraquinone derivatives.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20120215

Title: Comparison of dispersive liquid-liquid microextraction based on organic solvent and ionic liquid combined with high-performance liquid chromatography for the analysis of emodin and its metabolites in urine samples.

Journal: Journal of separation science 20120101

Title: Bioguided Fractionation Shows Cassia alata Extract to Inhibit Staphylococcus epidermidis and Pseudomonas aeruginosa Growth and Biofilm Formation.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: An overview of the evidence and mechanisms of herb-drug interactions.

Journal: Frontiers in pharmacology 20120101

Title: PCB 126 and other dioxin-like PCBs specifically suppress hepatic PEPCK expression via the aryl hydrocarbon receptor.

Journal: PloS one 20120101

Title: Exercise therapy for fibromyalgia.

Journal: Current pain and headache reports 20111001

Title: DNA-binding study of anthraquinone derivatives using chemometrics methods.

Journal: European journal of medicinal chemistry 20110701

Title: CFTR chloride channel as a molecular target of anthraquinone compounds in herbal laxatives.

Journal: Acta pharmacologica Sinica 20110601

Title: In vitro genotoxicity of danthron and its potential mechanism.

Journal: Mutation research 20110518

Title: Solid-phase extraction and ultra high-performance liquid chromatography tandem mass spectrometry analysis of the gastrointestinal absorption of emodin in different digestive segments of rats.

Journal: Journal of separation science 20110201

Title: Danthron functions as a retinoic X receptor antagonist by stabilizing tetramers of the receptor.

Journal: The Journal of biological chemistry 20110121

Title: Laxatives or methylnaltrexone for the management of constipation in palliative care patients.

Journal: The Cochrane database of systematic reviews 20110119

Title: Danthron, an anthraquinone derivative, induces DNA damage and caspase cascades-mediated apoptosis in SNU-1 human gastric cancer cells through mitochondrial permeability transition pores and Bax-triggered pathways.

Journal: Chemical research in toxicology 20110114

Title: Hypericins and thioredoxin reductase: Biochemical and docking studies disclose the molecular basis for effective inhibition by naphthodianthrones.

Journal: Bioorganic & medicinal chemistry 20110101

Title: In vitro study of the PLA2 inhibition and antioxidant activities of Aloe vera leaf skin extracts.

Journal: Lipids in health and disease 20110101

Title: Danthron inhibits murine WEHI-3 cells in vivo, and enhances macrophage phagocytosis and natural killer cell cytotoxic activity in leukemic mice.

Journal: In vivo (Athens, Greece) 20110101

Title: Intravitreal injection of methotrexate in an experimental rabbit model: determination of pharmacokinetics.

Journal: Indian journal of ophthalmology 20110101

Title: Drug nanoparticle formulation using ascorbic Acid derivatives.

Journal: Journal of drug delivery 20110101

Title: Phytochemical screening, antioxidant, and antimicrobial activities of the crude leaves' extract from Ipomoea batatas (L.) Lam.

Journal: Pharmacognosy magazine 20110101

Title: Danthron.

Journal: Report on carcinogens : carcinogen profiles 20110101

Title: Comparative study of intravenously administered clonidine and magnesium sulfate on hemodynamic responses during laparoscopic cholecystectomy.

Journal: Journal of anaesthesiology, clinical pharmacology 20110101

Title: A wireless sensor network for vineyard monitoring that uses image processing.

Journal: Sensors (Basel, Switzerland) 20110101

Title: Bioactive constituents and medicinal importance of genus Alnus.

Journal: Pharmacognosy reviews 20110101

Title: Synchrotron radiation linear dichroism (SRLD) investigation of the electronic transitions of quinizarin, chrysazin, and anthrarufin.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20100915

Title: Danthron induces DNA damage and inhibits DNA repair gene expressions in GBM 8401 human brain glioblastoma multiforms cells.

Journal: Neurochemical research 20100701

Title: 1,8-Dihydr-oxy-2,4,5,7-tetra-nitro-9,10-anthraquinone.

Journal: Acta crystallographica. Section E, Structure reports online 20100501

Title: Danthron induced apoptosis through mitochondria- and caspase-3-dependent pathways in human brain glioblastoma multiforms GBM 8401 cells.

Journal: Neurochemical research 20100301

Title: Potent inhibitor scaffold against Trypanosoma cruzi trans-sialidase.

Journal: Bioorganic & medicinal chemistry 20100215

Title: Anthraquinones danthron and quinizarin exert antiproliferative and antimetastatic activity on murine B16-F10 melanoma cells.

Journal: Anticancer research 20100201

Title: Enzymatic reduction of complex redox dyes using NADH-dependent reductase from Bacillus subtilis coupled with cofactor regeneration.

Journal: Applied microbiology and biotechnology 20100101

Title: 1,8-Bis(tos-yloxy)-9,10-anthraquinone.

Journal: Acta crystallographica. Section E, Structure reports online 20100101

Title: The coverage problem in video-based wireless sensor networks: a survey.

Journal: Sensors (Basel, Switzerland) 20100101

Title: Danthron inhibits the migration and invasion of human brain glioblastoma multiforme cells through the inhibition of mRNA expression of focal adhesion kinase, Rho kinases-1 and metalloproteinase-9.

Journal: Oncology reports 20091101

Title: Aloe-emodin-induced DNA fragmentation in the mouse in vivo comet assay.

Journal: Mutation research 20090801

Title: A 73-year-old man with long-term immobility presenting with abdominal pain.

Journal: PLoS medicine 20090701

Title: Differential inhibition of matrix metalloproteinases-2, -9, and -13 activities by selected anthraquinones.

Journal: Planta medica 20090301

Title: Structure-activity relationships of anthraquinones on the suppression of DNA-binding activity of the aryl hydrocarbon receptor induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.

Journal: Journal of bioscience and bioengineering 20090301

Title: A high-throughput approach for identification of novel general anesthetics.

Journal: PloS one 20090101

Title: Is senna laxative use associated to cathartic colon, genotoxicity, or carcinogenicity?

Journal: Journal of toxicology 20090101

Title: Dissociative photoionization mechanism of 1,8-dihydroxyanthraquinone: an experimental and theoretical study.

Journal: The journal of physical chemistry. A 20081030

Title: Correlation between reduction potentials and inhibitions of Epstein-Barr virus activation by anthraquinone derivatives.

Journal: Bioorganic & medicinal chemistry letters 20080715

Title: Study of interactions of anthraquinones with DNA using ethidium bromide as a fluorescence probe.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20080601

Title: On the interaction of the anthraquinone barbaloin with negatively charged DMPG bilayers.

Journal: Langmuir : the ACS journal of surfaces and colloids 20080415

Title: Solvent effect on the physical quenching of singlet molecular oxygen by p-quinones.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20080401

Title: Voltammetric Behavior of o-Nitrophenol and Damage to DNA.

Journal: International journal of molecular sciences 20080301

Title: Towards reconciling structure and function in the nuclear pore complex.

Journal: Histochemistry and cell biology 20080201

Title: Potential benefits of non-pharmacological therapies in fibromyalgia.

Journal: The open rheumatology journal 20080101

Title: Synthesis and antibacterial activity of some novel chiral fluorophoric biscyclic macrocycles.

Journal: Bioorganic & medicinal chemistry letters 20070915

Title: Simultaneous determination and pharmacokinetic studies of aloe emodin and chrysophanol in rats after oral administration of Da-Cheng-Qi decoction by high-performance liquid chromatography.

Journal: Biomedical chromatography : BMC 20070701

Title: Antiprotozoal activity of Senna racemosa.

Journal: Journal of ethnopharmacology 20070613

Title: Simultaneous quantification of five anthraquinones in rat plasma by high-performance liquid chromatography with fluorescence detection.

Journal: Biomedical chromatography : BMC 20070501

Title: Anthranoid laxatives influence the absorption of poorly permeable drugs in human intestinal cell culture model (Caco-2).

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20070401

Title: The right dose for every sex.

Journal: Chromosoma 20070401

Title: Reactivity of aromatic amines with triplet 1,8-dihydroxyanthraquinone: a laser flash photolysis study.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20070101

Title: Initial in vitro screening approach to investigate the potential health and environmental hazards of Enviroxtrade mark - a nanoparticulate cerium oxide diesel fuel additive.

Journal: Particle and fibre toxicology 20070101

Title: Laxatives for the management of constipation in palliative care patients.

Journal: The Cochrane database of systematic reviews 20061018

Title: Intramolecular hydrogen bonding in 1,8-dihydroxyanthraquinone, 1-aminoanthraquinone, and 9-hydroxyphenalenone studied by picosecond time-resolved fluorescence spectroscopy in a supersonic jet.

Journal: The journal of physical chemistry. B 20061012

Title: Microbial transformation of amino- and hydroxyanthraquinones by Beauveria bassiana ATCC 7159.

Journal: Journal of natural products 20061001

Title: Defensive components in insect eggs: are anthraquinones produced during egg development?

Journal: Journal of chemical ecology 20060901

Title: Electrocoagulation of quinone pigments.

Journal: Molecules (Basel, Switzerland) 20060714

Title: Interaction of anthracene and its oxidative derivatives with human serum albumin.

Journal: Acta biochimica Polonica 20060101

Title: [Toxic effects of 1,8-dihydroxyanthraquinone on Daphnia magna].

Journal: Ying yong sheng tai xue bao = The journal of applied ecology 20050601

Title: Electrochemical studies of danthron and the DNA-danthron interaction.

Journal: Biophysical chemistry 20050401

Title: Serially balanced designs for two sets of treatments.

Journal: Journal of biopharmaceutical statistics 20050101

Title: Oxoazabenzo[de]anthracenes conjugated to amino acids: synthesis and evaluation as DNA-binding antitumor agents.

Journal: Bioconjugate chemistry 20050101

Title: Growth responses of Cassia obtusifolia toward human intestinal bacteria.

Journal: Fitoterapia 20040701

Title: Danthron inhibits the neurotoxicity induced by various compounds causing oxidative damages including beta-amyloid (25-35) in primary cortical cultures.

Journal: Biological & pharmaceutical bulletin 20040501

Title: Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.

Journal: Journal of ethnopharmacology 20040401

Title: Methotrexate for ankylosing spondylitis.

Journal: The Cochrane database of systematic reviews 20040101

Title: Danthron (1,8-dihydroxyanthraquinone).

Journal: Report on carcinogens : carcinogen profiles 20040101

Title: Emodin isolated from Cassia obtusifolia (Leguminosae) seed shows larvicidal activity against three mosquito species.

Journal: Journal of agricultural and food chemistry 20031217

Title: Circular dichroism imaging microscopy: application to enantiomorphous twinning in biaxial crystals of 1,8-dihydroxyanthraquinone.

Journal: Journal of the American Chemical Society 20031203

Title: Factors influencing constipation in advanced cancer patients: a prospective study of opioid dose, dantron dose and physical functioning.

Journal: Palliative medicine 20030701

Title: Dithranol reaction with nitroxide radicals in DMSO, a HPLC study.

Journal: Die Pharmazie 20030701

Title: Inhibition of protein kinase CK2 by anthraquinone-related compounds. A structural insight.

Journal: The Journal of biological chemistry 20030117

Title: Antimutagenic effects of black tea (World Blend) and its two active polyphenols theaflavins and thearubigins in Salmonella assays.

Journal: Phytotherapy research : PTR 20021101

Title: 1,8-Dihydroxyanthraquinone anchored on silica gel: synthesis and application as solid phase extractant for lead(II), zinc(II) and cadmium(II) prior to their determination by flame atomic absorption spectrometry.

Journal: Talanta 20021016

Title: Enrichment of iron(III), cobalt(II), nickel(II), and copper(II) by solid-phase extraction with 1,8-dihydroxyanthraquinone anchored to silica gel before their determination by flame atomic absorption spectrometry.

Journal: Analytical and bioanalytical chemistry 20021001

Title: Bryoanthrathiophene, a new antiangiogenic constituent from the bryozoan Watersipora subtorquata (d'Orbigny, 1852).

Journal: Journal of natural products 20020901

Title: [Studies on the chemical constituents of Shiraia bambusicola].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20020901

Title: Cytotoxicity of rhein, the active metabolite of sennoside laxatives, is reduced by multidrug resistance-associated protein 1.

Journal: British journal of cancer 20020506

Title: Cytotoxicity of natural hydroxyanthraquinones: role of oxidative stress.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101

Title: Danthron (1,8-dihydroxyanthraquinone).

Journal: Report on carcinogens : carcinogen profiles 20020101

Title: Adverse effects of laxatives.

Journal: Diseases of the colon and rectum 20010801

Title: Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity.

Journal: Bioorganic & medicinal chemistry letters 20010723

Title: Sequence-specific DNA damage induced by carcinogenic danthron and anthraquinone in the presence of Cu(II), cytochrome P450 reductase and NADPH.

Journal: Free radical research 20010601

Title: Antipsoriatic anthrones with modulated redox properties. 5. Potent inhibition of human keratinocyte growth, induction of keratinocyte differentiation, and reduced membrane damage by novel 10-arylacetyl-1,8-dihydroxy-9(10H)-anthracenones.

Journal: Journal of medicinal chemistry 20010301

Title: In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus.

Journal: Antiviral research 20010301

Title: Heterocyclic substituted anthralin derivatives as inhibitors of keratinocyte growth and inducers of differentiation.

Journal: Bioorganic & medicinal chemistry letters 20010108

Title: Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19960903

Title: Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase.

Journal: Biochimica et biophysica acta 19951115

Title: Inhibitors of human immunodeficiency virus integrase.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19930315

Title: Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus.

Journal: Antiviral research 19920101

Title: Screening for new compounds with antiherpes activity.

Journal: Antiviral research 19841001

Title: Zhou R, et al. Danthron activates AMP-activated protein kinase and regulates lipid and glucose metabolism in vitro. Acta Pharmacol Sin. 2013 Aug;34(8):1061-9.

Title: Zhang H, et al. Danthron functions as a retinoic X receptor antagonist by stabilizing tetramers of the receptor. J Biol Chem. 2011 Jan 21;286(3):1868-75.

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Tags:117-10-2 Molecular Formula|117-10-2 MDL|117-10-2 SMILES|117-10-2 9,10-Anthracenedione, 1,8-dihydroxy-