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quinizarin
9,10-anthracenedione, 1,4-dihydroxy-

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Name:1,4-dihydroxyanthracene-9,10-dione
CAS Number: 81-64-1Picture of molecule3D/inchi
Other(deleted CASRN):103220-12-8
ECHA EINECS - REACH Pre-Reg:201-368-7
FDA UNII: 8S496ZV3CS
Nikkaji Web:J3.861J
Beilstein Number:1914036
MDL:MFCD00001209
XlogP3:3.70 (est)
Molecular Weight:240.21456000
Formula:C14 H8 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 200.00 °C. @ 760.00 mm Hg
Boiling Point: 465.30 °C. @ 760.00 mm Hg (est)
Flash Point: 481.00 °F. TCC ( 249.30 °C. ) (est)
logP (o/w): 3.719 (est)
Soluble in:
 water, 0.0961 mg/L @ 25 °C (exp)
 water, 3.426 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
1,4-Dihydroxyanthraquinone
Charkit Chemical
SOLVENT ORANGE 86
ExtraSynthese
For experimental / research use only.
1,4-Dihydroxyanthraquinone (HPLC) ≥95%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Quinizarin 96%
TCI AMERICA
For experimental / research use only.
Quinizarin >95.0%(HPLC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD > 10000 mg/kg
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(7), Pg. 93, 1990.

intravenous-mouse LD50 320 mg/kg
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03274

intraperitoneal-rat LD50 2100 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(12), Pg. 27, 1977.

oral-rat LD50 > 5000 mg/kg
National Technical Information Service. Vol. AD-A067-313

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
pharmaceuticals / chemical synthisis
Recommendation for quinizarin usage levels up to:
 not for fragrance use.
 
Recommendation for quinizarin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):81-64-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6688
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
1,4-dihydroxyanthracene-9,10-dione
Chemidplus:0000081641
RTECS:CB6600000 for cas# 81-64-1
 
References:
 1,4-dihydroxyanthracene-9,10-dione
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:81-64-1
Pubchem (cid):6688
Pubchem (sid):134972968
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2914.69.5000
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
9,10-anthracenedione, 1,4-dihydroxy-
 anthraquinone, 1,4-dihydroxy-
 chinizarin
1,4-dihydroxy-9,10-anthracene-dione
1,4-dihydroxy-9,10-anthracenedione
1,4-dihydroxy-9,10-anthraquinone
1,4-dihydroxy-anthraquinone
1,4-dihydroxyanthra-9,10-quinone
1,4-dihydroxyanthracene-9,10-dione
1,4-dihydroxyanthraquinone
1,4-dioxyanthraquinone
 macrolex orange GG
 smoke orange R
 solvent orange 86
 

Articles:

PubMed:Solvent effects on the photophysical properties of poly[1,4-dihydroxyanthraquinoneimine-1,3-bis(phenylene-ester-methylene)tetramethyldisiloxane].
PubMed:Characterization of Secondary Metabolites of an Endophytic Fungus from Curcuma wenyujin.
PubMed:Anthraquinones quinizarin and danthron unwind negatively supercoiled DNA and lengthen linear DNA.
PubMed:Digitally enhanced thin layer chromatography: further development and some applications in isotopic chemistry.
PubMed:Spectrophotometeric determination of trace amounts of Al3+ ion in water samples after cloud point extraction using quinizarin as a complexing agent.
PubMed:Combined spectral experiment and theoretical calculation to study the interaction of 1,4-dihydroxyanthraquinone for metal ions in solution.
PubMed:Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions.
PubMed:Evaluation of natural anthracene-derived compounds as antimitotic agents.
PubMed:Spectroscopic and in silico evaluation of interaction of DNA with six anthraquinone derivatives.
PubMed:Polymerization of novel methacrylated anthraquinone dyes.
PubMed:Anthraquinone derivative O,O'-bis-(3'-iodopropyl)-1,4-dihydroxyanthraquinone modulates immune response and improves experimental autoimmune encephalomyelitis.
PubMed:Solubilization of two organic dyes by cationic ester-containing gemini surfactants.
PubMed:The adsorption of quinizarin on boron-doped diamond.
PubMed:DNA-binding, DNA cleavage and cytotoxicity studies of two anthraquinone derivatives.
PubMed:An investigation of anthraquinone dye biodegradation by immobilized Aspergillus flavus in fluidized bed bioreactor.
PubMed:Electrospun 1,4-DHAQ-doped cellulose nanofiber films for reusable fluorescence detection of trace Cu2+ and further for Cr3+.
PubMed:The electrochemistry of quinizarin revealed through its mediated reduction of oxygen.
PubMed:Effects of new quinizarin derivatives on both HCV NS5B RNA polymerase and HIV-1 reverse transcriptase associated ribonuclease H activities.
PubMed:Hyperbranched polyethylenimine bearing cyclodextrin moieties showing temperature and pH controlled dye release.
PubMed:Synthesis of a 4H-anthra[1,2-b]pyran derivative and its antimicrobial activity.
PubMed:Synthesis and antiproliferative activity of 1,4-bis(dimethylamino)-9,10-anthraquinone derivatives against P388 mouse leukemic tumor cells.
PubMed:Discrete half-sandwich Ir, Rh-based organometallic molecular boxes: synthesis, characterization, and their properties.
PubMed:Theoretical study of molecular structure and vibrational spectra of 1,4-dihydroxyanthraquinone.
PubMed:DNA-binding study of anthraquinone derivatives using chemometrics methods.
PubMed:Comparison of sorption behavior of Th(IV) and U(VI) on modified impregnated resin containing quinizarin with that conventional prepared impregnated resin.
PubMed:Solid phase synthesis and biological activity of tuftsin conjugates.
PubMed:An HPLC method development for the assessment of degradation products of anthraquinone dye.
PubMed:Synchrotron radiation linear dichroism (SRLD) investigation of the electronic transitions of quinizarin, chrysazin, and anthrarufin.
PubMed:Anthraquinones danthron and quinizarin exert antiproliferative and antimetastatic activity on murine B16-F10 melanoma cells.
PubMed:Studies on the formation of a complex of Cu(II) with sodium 1,4-dihydroxy-9,10-anthraquinone-2-sulphonate - an analogue of the core unit of anthracycline anticancer drugs and its interaction with calf thymus DNA.
PubMed:Infrared-induced coherent vibration of a hydrogen-bonded system: effects of mechanical and electrical anharmonic couplings.
PubMed:Interfacial electron transfer dynamics in quinizarin sensitized ZnS nanoparticles: monitoring charge transfer emission.
PubMed:The comparative toxicity to soil invertebrates of natural chemicals and their synthetic analogues.
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:Host-guest interaction of 1,4-dihydroxy-9,10-anthraquinone (quinizarin) with cyclodextrins.
PubMed:Decomposition of polycyclic aromatic hydrocarbons in atmospheric aqueous droplets through sulfate anion radicals: an experimental and theoretical study.
PubMed:Ionic liquid-promoted ring-closure reactions between 1,4-dihydroxyanthraquinone and diamines.
PubMed:Determination of lithium in pharmaceutical formulations used in the treatment of bipolar disorder by flow injection analysis with spectrophotometric detection.
PubMed:HPLC-MS of anthraquinoids, flavonoids, and their degradation products in analysis of natural dyes in archeological objects.
PubMed:Micellar electrokinetic chromatography method for the determination of several natural red dyestuff and lake pigments used in art work.
PubMed:Involvement of Tetrahymena pyriformis and selected fungi in the elimination of anthracene, and toxicity assessment of the biotransformation products.
PubMed:Kinetics of the substitution of dehydroacetic acid in tris (dehydroacetato) Fe(III) complex by 8-hydroxyquinoline, di- and tetra-hydroxyquinone.
PubMed:Electron injection into the surface states of ZrO2 nanoparticles from photoexcited quinizarin and its derivatives: effect of surface modification.
PubMed:Interaction of anthracene and its oxidative derivatives with human serum albumin.
PubMed:Induction of extracellular matrix synthesis in normal human fibroblasts by anthraquinone isolated from Morinda citrifolia (Noni) fruit.
PubMed:Identification of natural dyes used in works of art by pyrolysis-gas chromatography/mass spectrometry combined with in situ trimethylsilylation.
PubMed:Determination of back electron transfer rate from the surface states of quinizarin-sensitized ZrO2 nanoparticles by monitoring charge transfer emission.
PubMed:Growth responses of Cassia obtusifolia toward human intestinal bacteria.
PubMed:Emodin isolated from Cassia obtusifolia (Leguminosae) seed shows larvicidal activity against three mosquito species.
PubMed:Evaluation of hypersensitivity to anthraquinone-related substances.
PubMed:[mRNA level and cytochrome P450 1A activity in the liver of C57BL mice induced by various xenobiotics].
PubMed:Peroxidase-mediated transformation of hydroxy-9,10-anthraquinones.
PubMed:Enantioselective synthesis of (+)-4-demethoxy-1,4-dimethyldaunomycinone.
PubMed:Sensitizer contained in heat-decomposed dye.
PubMed:Linkage and redox isomerism in ruthenium complexes of catecholate, semiquinone, and o-acylphenolate ligands derived from 1,2-dihydroxy-9,10-anthracenedione (alizarin) and related species: syntheses, characterizations, and photophysics.
PubMed:1,4-Anthraquinone: an anticancer drug that blocks nucleoside transport, inhibits macromolecule synthesis, induces DNA fragmentation, and decreases the growth and viability of L1210 leukemic cells in the same nanomolar range as daunorubicin in vitro.
PubMed:How Fe3+ binds anthracycline antitumour compounds. The myth and the reality of a chemical sphinx.
PubMed:Development and validation of a spectrophotometric dye immersion test method used to measure container-closure integrity of an oil-based product.
PubMed:Spectrophotometric determination of lithium with Quinizarin in drugs and serum.
PubMed:Selective spectrofluorometric determination of lithium(I) with quinizarin by extraction into tributyl phosphate.
PubMed:Comparison of responses of DNA topoisomerase I from Candida albicans and human cells to four new agents which stimulate topoisomerase-dependent DNA nicking.
PubMed:Structure-activity relationships of anthraquinones as inhibitors of 7-ethoxycoumarin O-deethylase and mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline.
PubMed:Synthesis and conformational preference of novel 8-fluoroanthracyclines.
PubMed:Cardiovascular and sweating dysfunction in patients with Holmes-Adie syndrome.
PubMed:A theoretical study of the mechanism of oxygen binding by model anthraquinones. Part II. Quantum-mechanical studies of the energetics of oxygen binding to model anthraquinones.
PubMed:Generation of large radical ions from oligometallocenes by matrix-assisted laser desorption ionization.
PubMed:Spinal mediation of thermally induced sweating.
PubMed:Interpreting the visible absorption bands of 1,4-(dihydroxy)-9,10-anthraquinone and its metal chelates.
PubMed:[Total synthesis of oxa-9-anthracyclines].
PubMed:Polarographic determination of 9,10-anthraquinone and its 1,2- 1,4- and 1,8-dihydroxy derivatives in chloroform Application to the analysis of papers and black liquors.
PubMed:A graphical derivative approach to the photometric determination of lutetium and praseodymium in mixtures.
PubMed:EPR studies of copper(II) and cobalt(II) complexes of adriamycin.
PubMed:Genotoxicity in the hepatocyte/DNA repair test and toxicity to liver mitochondria of 1-hydroxyanthraquinone and several dihydroxyanthraquinones.
PubMed:Linewidth study of the dye molecule quinizarin in solid alcohol glasses.
PubMed:A comparative study of some hydroxyanthraquinones as acid-base indicators.
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:Study of 1,4-dihydroxyanthraquinone as an acid-base indicator in isopropyl alcohol medium Evaluation of colour-change limits through complementary chromaticity parameters.
PubMed:Synthesis of simian virus 40 chromosomes in nuclear extracts from dihydroxyanthraquinone-treated cells.
PubMed:Mutagenicity of anthraquinone and hydroxylated anthraquinones in the Ames/Salmonella microsome system.
PubMed:[New anthraquinones in Rubia cordifolia roots].
PubMed:The immunoinhibitory and immunostimulatory effects of hydroxyanthra- and hydroxynaphthoquinone derivatives.
PubMed:Antitumor agents. 1. 1,4-Bis[(aminoalkyl)amino]-9,10-anthracenediones.
PubMed:Color additives. Determination of 1,4-dihydroxyanthraquinone in D&C green no. 5 and the former external D&C violet no. 2.
PubMed:Computer-assisted study of the complexation of quinizarin-2-sulphonic acid with iron(III).
PubMed:Purification and characterizing properties of analytical reagent quinizarin-2-sulphonic acid and its sodium salt.
PubMed:Eccrine Function in Psoriasis Inversus.
PubMed:The management of the quinizarin sweat test.
PubMed:The management of the quinizarin sweat test (Q.S.T.).
 
Notes:
None found
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