Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H8O2 |
Molecular Weight | 208.2121 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1C2=C(C=CC=C2)C(=O)C3=C1C=CC=C3
InChI
InChIKey=RZVHIXYEVGDQDX-UHFFFAOYSA-N
InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H
DescriptionSources: DOI: 10.1002/0471238961.0114200803150618.a01Curator's Comment: Description was created based on several sources, including:
http://www.fda.gov/downloads/Food/IngredientsPackagingLabeling/GRAS/NoticeInventory/ucm267578.pdf
https://monographs.iarc.fr/ENG/Monographs/vol82/mono82-6C.pdf
http://nopr.niscair.res.in/bitstream/123456789/14810/1/IJNPR%203(3)%20291-319.pdf
Sources: DOI: 10.1002/0471238961.0114200803150618.a01
Curator's Comment: Description was created based on several sources, including:
http://www.fda.gov/downloads/Food/IngredientsPackagingLabeling/GRAS/NoticeInventory/ucm267578.pdf
https://monographs.iarc.fr/ENG/Monographs/vol82/mono82-6C.pdf
http://nopr.niscair.res.in/bitstream/123456789/14810/1/IJNPR%203(3)%20291-319.pdf
Anthraquinone has yet to be found in nature. Of all the quinones found naturally, those derived from anthraquinone far exceed all others. Many of these are found in molds. Derivatives of 9,10-anthracenedione (anthraquinones) with several hydroxy and other functional groups are biologically active compounds isolated from Rubia and Cassia medical plant species. Anthraquinone is a comparatively safe compound: LD50 (rat) is 3500 mg/kg. It is a mild allergen and, as a fine powder, may cause skin irritation. Exposure to 3,000 ppm may be tolerated for only 30–60 min after which irritation of the nose, throat, and lungs may occur along with headaches, dizziness, and slurred speech. 9,10-anthraquinone is a weak carcinogen. Aside from its major use in the manufacture of intermediates for anthraquinone dyes and pigments, anthraquinone is finding increasing interest as a catalyst in the pulping of wood, in the polymerization of various materials for plastics, and in the isomerization of vegetable oils. It has been used to make seeds distasteful to birds (bird repellent) and as an accelerator in nickel electroplating.
Originator
Sources: https://books.google.ru/books?id=qxCFXiFEAtAC
Curator's Comment: Ueber verschiedene Verbindungen des Anthracen’s. p.287
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2487 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19309732 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Reactive dyes decolouration by TiO2 photo-assisted catalysis. | 2001 |
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Possible cause of G-C-->C-G transversion mutation by guanine oxidation product, imidazolone. | 2001 Apr |
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Aryl hydrocarbon receptor-mediated and estrogenic activities of oxygenated polycyclic aromatic hydrocarbons and azaarenes originally identified in extracts of river sediments. | 2001 Dec |
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Determination of pKa values of anthraquinone compounds by capillary electrophoresis. | 2001 Feb |
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[Adsorption of anthraquinone dyes by biosorbent GX2]. | 2001 Jan |
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[Studies on the anthraquinones of Cassia siamea]. | 2001 Jul |
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Quantum yield study of the photodegradation of hydrophobic dyes in the presence of acetone sensitizer. | 2001 Jul |
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Cytotoxic and DNA damage-inducing activities of low molecular weight phenols from rhubarb. | 2001 Jul-Aug |
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Sequence-specific DNA damage induced by carcinogenic danthron and anthraquinone in the presence of Cu(II), cytochrome P450 reductase and NADPH. | 2001 Jun |
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Mutagenicity of natural anthraquinones from Rubia tinctorum in the Drosophila wing spot test. | 2001 Mar |
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The preparation of anthraquinone used in the National Toxicology Program cancer bioassay was contaminated with the mutagen 9-nitroanthracene. | 2001 Mar |
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Photocatalytic degradation of acid blue 80 in aqueous solutions containing TiO2 suspensions. | 2001 Mar 1 |
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No induction of chromosomal aberrations in Chinese hamster ovary cells by chrysophanol. | 2001 May 31 |
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Dye-ligand affinity systems. | 2001 Oct 30 |
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Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5. | 2001 Sep |
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Decolorization of an anthraquinone-type dye using a laccase formulation. | 2001 Sep |
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Photochemical synthesis of aldehydes in the solid phase. | 2002 Apr 19 |
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Studies toward the total synthesis of mumbaistatin, a highly potent glucose-6-phosphate translocase inhibitor. Synthesis of a mumbaistatin analogue. | 2002 Dec 27 |
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Structure of acid-stable carmine. | 2002 Feb |
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Dye-ligand affinity adsorbents for enzyme purification. | 2002 Jan |
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Antifeedant activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F. | 2002 May |
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Synthesis of 11-hydroxyl O-methylsterigmatocystin and the role of a cytochrome P-450 in the final step of aflatoxin biosynthesis. | 2002 May 15 |
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Cytotoxicity of rhein, the active metabolite of sennoside laxatives, is reduced by multidrug resistance-associated protein 1. | 2002 May 6 |
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Inducible nitric oxide synthase inhibitors of Chinese herbs III. Rheum palmatum. | 2002 Oct |
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Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin. | 2002 Oct 31 |
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Effects of polyphenolic anthrone derivatives, resistomycin and hypercin, on apoptosis in human megakaryoblastic leukemia CMK-7 cell line. | 2002 Sep-Oct |
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New propylamine oligopyrrole carboxamides linked to a heterocyclic or anthraquinone system: synthesis, DNA binding, topoisomerase I inhibition and cytotoxicity. | 2003 Feb |
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Effects of 9,10 anthraquinone on ruminal fermentation, total-tract digestion, and blood metabolite concentrations in sheep. | 2003 Jan |
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Pharmacokinetic analysis of rhein in Rheum undulatum L. | 2003 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: For use only as a pulping aid in the alkaline pulping of lignocellulosic material at levels not to exceed 0.1 percent by weight of the raw lignocellulosic material.
https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=176.170
Unknown
Route of Administration:
Unknown
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19309732
9,10-anthraquinone at concentration 100uM is able to impair β-amyloid peptides (Aβ) aggregation
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CFR |
21 CFR 176.170
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EPA PESTICIDE CODE |
122701
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NCI_THESAURUS |
C737
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ANTHRAQUINONE
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7957
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C042834
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2074
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anthraquinone
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SUB34652
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1482551
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100000128041
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030MS0JBDO
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C26451
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6780
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84-65-1
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40448
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m1949
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DTXSID3020095
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030MS0JBDO
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201-549-0
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ACTIVE MOIETY