1,8-dihydroanthraquinone

CAS: 117-10-2 C14 H8 O4 MW: 240.21456000

Identification

Namedanthron
IUPAC1,8-dihydroxyanthracene-9,10-dione
CAS Number117-10-2
EINECS204-173-5
FDA UNIIZ4XE6IBF3V
Molecular FormulaC14 H8 O4
Molecular Weight240.21456000
MDL NumberMFCD00001211
Nikkaji NumberJ2.905J
Beilstein2054727
XlogP33.20 (est)

Regulatory

Physical Properties

Appearance orange crystalline powder (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 193.00 °C. @ 760.00 mm Hg
Boiling Point 452.70 °C. @ 760.00 mm Hg (est)
Vapor Pressure 8.600000 mmHg @ 25.00 °C. (est)
Vapor Density 8.3 ( Air = 1 )
Flash Point 467.00 °F. TCC ( 241.70 °C. ) (est)
logP (o/w) 4.570 (est)
Soluble in water, 3.426 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 500 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for danthron usage levels up tonot for fragrance use.
Recommendation for danthron flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

rheum palmatum root

Synonyms

9,10- anthracenedione, 1,8-dihydroxy- anthraquinone, 1,8-dihydroxy- antrapurol bancon chrysazin chrysazine criasazin danivac danthrone dantron dantrone dantronum dianthon diaquone 9,10- dihydro-1,8-dihydroxy-9,10-dioxoanthracene 1,8- dihydroanthraquinone 1,8- dihydroxy-9,10-anthracenedione, 9CI 1,8- dihydroxy-9,10-anthraquinone 1,8- dihydroxy-9,10-dihydroanthracene-9,10-dione 1,8- dihydroxyanthra-9,10-quinone 1,8- dihydroxyanthracene-9,10-dione 1,8- dihydroxyanthrachinon 1,8- dihydroxyanthraquinone dionone 1,8- dioxyanthraquinone dorbane dorbanex dorbantyl duolax istizin laxanorm laxanthreen laxapur laxipur laxipurin neokutin S 1,8-bis( oxidanyl)anthracene-9,10-dione pastomin prugol roydan scatron D 1,4,5,8- tetroxyantraquinone zwitsalax PubMed: In vitro glucuronidation of five rhubarb anthraquinones by intestinal and liver microsomes from humans and rats. PubMed: Anthraquinones quinizarin and danthron unwind negatively supercoiled DNA and lengthen linear DNA. PubMed: Danthron activates AMP-activated protein kinase and regulates lipid and glucose metabolism in vitro. PubMed: Spectroscopic and in silico evaluation of interaction of DNA with six anthraquinone derivatives. PubMed: A new dibenz[b,e]oxepine derivative, 1-hydroxy-10-methoxy-dibenz[b,e]oxepin-6,11-dione, from a marine-derived fungus, Beauveria bassiana TPU942. PubMed: 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). PubMed: Colorimetric and fluorescence sensing of Cu2+ in water using 1,8-dihydroxyanthraquinone-β-cyclodextrin complex with the assistance of ammonia. PubMed: Danthron triggers ROS and mitochondria-mediated apoptotic death in C6 rat glioma cells through caspase cascades, apoptosis-inducing factor and endonuclease G multiple signaling. PubMed: Bioguided Fractionation Shows Cassia alata Extract to Inhibit Staphylococcus epidermidis and Pseudomonas aeruginosa Growth and Biofilm Formation. PubMed: DNA-binding, DNA cleavage and cytotoxicity studies of two anthraquinone derivatives. PubMed: 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. PubMed: Danthron. PubMed: Danthron inhibits murine WEHI-3 cells in vivo, and enhances macrophage phagocytosis and natural killer cell cytotoxic activity in leukemic mice. PubMed: DNA-binding study of anthraquinone derivatives using chemometrics methods. PubMed: In vitro genotoxicity of danthron and its potential mechanism. PubMed: Laxatives or methylnaltrexone for the management of constipation in palliative care patients. PubMed: 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. PubMed: Danthron functions as a retinoic X receptor antagonist by stabilizing tetramers of the receptor. PubMed: Synchrotron radiation linear dichroism (SRLD) investigation of the electronic transitions of quinizarin, chrysazin, and anthrarufin. PubMed: Danthron induces DNA damage and inhibits DNA repair gene expressions in GBM 8401 human brain glioblastoma multiforms cells. PubMed: Anthraquinones danthron and quinizarin exert antiproliferative and antimetastatic activity on murine B16-F10 melanoma cells. PubMed: 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. PubMed: Danthron induced apoptosis through mitochondria- and caspase-3-dependent pathways in human brain glioblastoma multiforms GBM 8401 cells. PubMed: Aloe-emodin-induced DNA fragmentation in the mouse in vivo comet assay. PubMed: 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. PubMed: Dissociative photoionization mechanism of 1,8-dihydroxyanthraquinone: an experimental and theoretical study. PubMed: Study of interactions of anthraquinones with DNA using ethidium bromide as a fluorescence probe. PubMed: Anthranoid laxatives influence the absorption of poorly permeable drugs in human intestinal cell culture model (Caco-2). PubMed: Laxatives for the management of constipation in palliative care patients. PubMed: Defensive components in insect eggs: are anthraquinones produced during egg development? PubMed: Reactivity of aromatic amines with triplet 1,8-dihydroxyanthraquinone: a laser flash photolysis study. PubMed: [Toxic effects of 1,8-dihydroxyanthraquinone on Daphnia magna]. PubMed: Electrochemical studies of danthron and the DNA-danthron interaction. PubMed: Danthron (1,8-dihydroxyanthraquinone). PubMed: Danthron inhibits the neurotoxicity induced by various compounds causing oxidative damages including beta-amyloid (25-35) in primary cortical cultures. PubMed: Danthron (1,8-dihydroxyanthraquinone). PubMed: Emodin isolated from Cassia obtusifolia (Leguminosae) seed shows larvicidal activity against three mosquito species. PubMed: Factors influencing constipation in advanced cancer patients: a prospective study of opioid dose, dantron dose and physical functioning. PubMed: [Studies on the chemical constituents of Shiraia bambusicola]. PubMed: Cytotoxicity of natural hydroxyanthraquinones: role of oxidative stress. PubMed: Antimutagenic effects of black tea (World Blend) and its two active polyphenols theaflavins and thearubigins in Salmonella assays. PubMed: 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. PubMed: Bryoanthrathiophene, a new antiangiogenic constituent from the bryozoan Watersipora subtorquata (d'Orbigny, 1852). PubMed: Cytotoxicity of rhein, the active metabolite of sennoside laxatives, is reduced by multidrug resistance-associated protein 1. PubMed: Sequence-specific DNA damage induced by carcinogenic danthron and anthraquinone in the presence of Cu(II), cytochrome P450 reductase and NADPH. PubMed: Adverse effects of laxatives. PubMed: Inhibition of cell growth in culture by quinones. PubMed: The irritancy of anthralin is inhibited by repeat applications of a subirritant concentration. PubMed: Antimutagenic effects of centchroman--a contraceptive and a candidate drug for breast cancer in multiple mutational assays. PubMed: Laxative drug products for over-the-counter human use. Food and Drug Administration, HHS. Final rule. PubMed: Anthraquinone cytotoxicity and apoptosis in primary cultures of rat hepatocytes. PubMed: Occurrence of emodin, chrysophanol and physcion in vegetables, herbs and liquors. Genotoxicity and anti-genotoxicity of the anthraquinones and of the whole plants. PubMed: Characterization of the genotoxicity of anthraquinones in mammalian cells. PubMed: Factors affecting the genotoxic potency ranking of natural anthraquinones in mammalian cell culture systems. PubMed: Enhancement of cell proliferation and prostaglandin biosynthesis by 1,8-dihydroxyanthraquinone in the rat large intestine. PubMed: Genotoxicity of the laxative drug components emodin, aloe-emodin and danthron in mammalian cells: topoisomerase II mediated? PubMed: Inactivation of mouse epidermal 12-lipoxygenase by anthralin--implications for the role of oxygen radicals. PubMed: Biotransformation of benzo[a]pyrene and other polycyclic aromatic hydrocarbons and heterocyclic analogs by several green algae and other algal species under gold and white light. PubMed: OTC pharmaceuticals and genotoxicity testing: the paracetamol, anthraquinone, and griseofulvin cases. PubMed: Effects of long-term treatment with anthranoids and sodium picosulphate on the contents of vasoactive intestinal polypeptide, somatostatin and substance P in the rat colon. PubMed: Cell proliferation induced by laxatives and related compounds in the rat intestine. PubMed: Toxicity of structurally related anthraquinones and anthrones to mammalian cells in vitro. PubMed: Promoting and synergistic effects of chrysazin on 1,2-dimethylhydrazine-induced carcinogenesis in male ICR/CD-1 mice. PubMed: Adverse effects of drugs used in the management of constipation and diarrhoea. PubMed: Analytics of senna drugs with regard to the toxicological discussion of anthranoids. PubMed: Light and electron-microscopic changes in the colon of the guinea pig after treatment with anthranoid and non-anthranoid laxatives. PubMed: Chronic sennoside treatment does not cause habituation and secondary hyperaldosteronism in rats. PubMed: Effects of long-term sennoside treatment on in vitro motility of rat colon. PubMed: A note on the complex metabolism of danthron infused into the rat. PubMed: Rhein and aloe-emodin kinetics from senna laxatives in man. PubMed: Pharmacokinetic-metabolic studies with 14C-aloe emodin after oral administration to male and female rats. PubMed: A rapid high-performance thin-layer chromatographic urine screen for laxative abuse. PubMed: Down-regulation of epidermal growth factor receptors by dithranol. PubMed: Laxative-induced contact dermatitis. PubMed: Inhibition of human monocyte functions by anthralin. PubMed: Effects of long-term laxative treatment on neuropeptides in rat mesenteric vessels and caecum. PubMed: Mutagenicity of substituted anthraquinones in the Ames/Salmonella microsome system. PubMed: Radical-mediated modification of deoxyguanine and deoxyribose by luteoskyrin and related anthraquinones. PubMed: Dithranol-induced down-regulation of 12(S)-hydroxyeicosatetraenoic acid [12(S)-HETE] receptors in a human epidermal cell line. PubMed: Spectroscopic studies of cutaneous photosensitizing agents--XV. Anthralin and its oxidation product 1,8-dihydroxyanthraquinone. PubMed: Effects of long-term laxative treatment on rat mesenteric resistance vessel responses in vitro. PubMed: Hydroxyanthraquinones as tumor promoters: enhancement of malignant transformation of C3H mouse fibroblasts and growth stimulation of primary rat hepatocytes. PubMed: Resistance of myenteric neurons in the rat's colon to depletion by 1,8-dihydroxyanthraquinone. PubMed: Dantron (chrysazin; 1,8-dihydroxyanthraquinone) PubMed: Relative metabolism of quinones to semiquinone radicals in xanthine oxidase system. PubMed: Normal-phase and reversed-phase liquid chromatographic techniques for the determination of dithranol and its degradation products. PubMed: Anthraquinone laxatives and human cancer: an association in one case. PubMed: Anthralin, a non-phorbol tumor promoter, fails to inhibit metabolic cooperation in mutant human fibroblasts, but inhibits phytohemagglutinin-induced lymphocyte blastogenesis in vitro. PubMed: Screening procedure for stimulant laxatives in urine using high-performance liquid chromatography with diode array detection. PubMed: Effects of withdrawal of co-danthramer on use of laxatives in a district general hospital. PubMed: Pigmentation of kidneys and lymph nodes of mesocolon in rats fed diets containing the laxative danthron. PubMed: Danthron alarm, FDA response: crucial OTC drug control. PubMed: Laxatives: replacing danthron. PubMed: Melanosis coli. A consequence of anthraquinone-induced apoptosis of colonic epithelial cells. PubMed: Inclusion complex formation of 1,8-dihydroxyanthraquinone with cyclodextrins in aqueous solution and in solid state. PubMed: Oxidation of antipsoriatic 10-acyldithranol derivatives and dithranol to 1,8-dihydroxyanthraquinone. PubMed: Patch testing with dithranol and its degradation products. PubMed: Long-term mucosal alterations by sennosides and related compounds. PubMed: Anthraquinone laxatives: metabolism and transport of danthron and rhein in the rat small and large intestine in vitro. PubMed: New aspects on the metabolism of the sennosides. PubMed: [Reactions and interactions of drugs according to "Drug Reactions and Interactions" by P.F. D'Arcy]. PubMed: Studies on laxatives: biliary and urinary excretion in rats given danthron by intravenous infusion or gastric intubation. PubMed: Anthralin stability in various vehicles. PubMed: [Danthron prohibition]. PubMed: The release and percutaneous permeation of anthralin products, using clinically involved and uninvolved psoriatic skin. PubMed: [Stability of cignolin (dithranol) in ointments containing tar with and without the addition of salicylic acid. Oxidation to danthron and dithranol dimer]. PubMed: [Mode of action of anthraquinone laxatives on the rat]. PubMed: The detection of laxative abuse. PubMed: Biotransformation of the carcinogen chrysazin by NADPH-microsome system. PubMed: Anthralin (1,8-dihydroxyanthrone) is a potent inhibitor of leukotriene production and LTB4-omega oxidation by human neutrophils. PubMed: Carcinogenicity of chrysazin in large intestine and liver of mice. PubMed: Acceleration of large intestine transit time in rats by sennosides and related compounds. PubMed: Induction of intestinal tumours in rats by chrysazin. PubMed: Comparative physiological disposition of some anthraquinone glycosides and aglycones. PubMed: Multifunctional inhibition by anthralin in nonstimulated and chemotactic factor stimulated human neutrophils. PubMed: [The study of the synthesis of the antineoplastic agent DHAQ]. PubMed: Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by tannic acid, hydroxylated anthraquinones and hydroxylated cinnamic acid derivatives. PubMed: Antirespiratory and antiproliferative activity of anthralin in cultured human keratinocytes. PubMed: Experimental contribution to the dithranol-brown problem. PubMed: Ultrastructure of mouse intestinal mucosa and changes observed after long term anthraquinone administration. PubMed: A cutaneous complication of Dorbanex therapy. PubMed: Laxative eruption. PubMed: Mutagenicity of quinones: pathways of metabolic activation and detoxification. PubMed: A cutaneous complication of Dorbanex therapy. PubMed: Anthralin inhibition of mouse epidermal arachidonic acid lipoxygenase in vitro. PubMed: Effect of indomethacin on aloin and 1,8 dioxianthraquinone-induced production of prostaglandins in rat isolated colon. PubMed: [Side effects of anthralin and its 2 main impurities on healthy skin]. PubMed: [Colon cleansing: a comparative study]. PubMed: Constipation in long-stay elderly patients: its treatment and prevention by lactulose, poloxalkol-dihydroxyanthroquinolone and phosphate enemas. PubMed: [Perianal toxic contact dermatitis after use of the laxative Dorbantyl]. PubMed: On the stability of some antipsoriatic active anthralin (dithranol) derivatives. PubMed: Inhibition of DNA replication and repair by anthralin or danthron in cultured human cells. PubMed: Mutagenicity of anthraquinone and hydroxylated anthraquinones in the Ames/Salmonella microsome system. PubMed: Inhibition of DNA replication and repair cultured humans cells by anthralin or danthron. PubMed: Influence of 1,8-dihydroxyanthraquinone and loperamide on the paracellular permeability across colonic mucosa. PubMed: A screening method for establishing laxative abuse. PubMed: [Clastogenic action of an anthraquinone compound on human lymphocytes]. PubMed: [Tienilic acid as a likely cause of "auto immune" active hepatitis (author's transl)]. PubMed: Danthron induced melanosis coli in the guinea pig. PubMed: Acute mouse and chronic dog toxicity studies of danthron, dioctyl sodium sulfosuccinate, poloxalkol and combinations. PubMed: Possible hepatotoxicity of Doxidan. PubMed: Danthron/poloxalkol and placebo in puerperal constipation. PubMed: [An interesting drug for the treatment of constipation: the association of calcium pantothenate and danthron]. PubMed: [Clinical trials of treatment of chronic constipation with a surface-active and hydrotropic agent in oral administration (dioctyl sodium sulfosuccinate with danthron). 64 cases, 41 of these assembled in a table]. PubMed: [Clinical trial of a combination: calcium pantothenate-danthron in 28 cases of constipation of various etiologies]. PubMed: INFLUENCE OF AN ORAL PERISTALTIC STIMULANT, DANTHRON, ON THE PHENOLSULPHONPHTHALEIN EXCRETION TEST. PubMed: Treatment of chronic functional constipation with dioctyl sodium sulfosuccinate and danthron. PubMed: Peristalticstimulating and fecal-hydrating properties of dioctyl sodium sulfosuccinate, danthron, and cascara extracts in the mouse and rat. PubMed: Use of doxinate with danthron as withdrawal therapy in the treatment of chronic functional constipation.