U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ANTHRAQUINONE

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

HIDE SMILES / InChI

Description
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

Curator's Comment: Ueber verschiedene Verbindungen des Anthracen’s. p.287

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Reactive dyes decolouration by TiO2 photo-assisted catalysis.
2001
Possible cause of G-C-->C-G transversion mutation by guanine oxidation product, imidazolone.
2001 Apr
Aryl hydrocarbon receptor-mediated and estrogenic activities of oxygenated polycyclic aromatic hydrocarbons and azaarenes originally identified in extracts of river sediments.
2001 Dec
Determination of pKa values of anthraquinone compounds by capillary electrophoresis.
2001 Feb
[Adsorption of anthraquinone dyes by biosorbent GX2].
2001 Jan
[Studies on the anthraquinones of Cassia siamea].
2001 Jul
Quantum yield study of the photodegradation of hydrophobic dyes in the presence of acetone sensitizer.
2001 Jul
Cytotoxic and DNA damage-inducing activities of low molecular weight phenols from rhubarb.
2001 Jul-Aug
Sequence-specific DNA damage induced by carcinogenic danthron and anthraquinone in the presence of Cu(II), cytochrome P450 reductase and NADPH.
2001 Jun
Mutagenicity of natural anthraquinones from Rubia tinctorum in the Drosophila wing spot test.
2001 Mar
The preparation of anthraquinone used in the National Toxicology Program cancer bioassay was contaminated with the mutagen 9-nitroanthracene.
2001 Mar
Photocatalytic degradation of acid blue 80 in aqueous solutions containing TiO2 suspensions.
2001 Mar 1
No induction of chromosomal aberrations in Chinese hamster ovary cells by chrysophanol.
2001 May 31
Dye-ligand affinity systems.
2001 Oct 30
Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5.
2001 Sep
Decolorization of an anthraquinone-type dye using a laccase formulation.
2001 Sep
Photochemical synthesis of aldehydes in the solid phase.
2002 Apr 19
Studies toward the total synthesis of mumbaistatin, a highly potent glucose-6-phosphate translocase inhibitor. Synthesis of a mumbaistatin analogue.
2002 Dec 27
Structure of acid-stable carmine.
2002 Feb
Dye-ligand affinity adsorbents for enzyme purification.
2002 Jan
Antifeedant activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F.
2002 May
Synthesis of 11-hydroxyl O-methylsterigmatocystin and the role of a cytochrome P-450 in the final step of aflatoxin biosynthesis.
2002 May 15
Cytotoxicity of rhein, the active metabolite of sennoside laxatives, is reduced by multidrug resistance-associated protein 1.
2002 May 6
Inducible nitric oxide synthase inhibitors of Chinese herbs III. Rheum palmatum.
2002 Oct
Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin.
2002 Oct 31
Effects of polyphenolic anthrone derivatives, resistomycin and hypercin, on apoptosis in human megakaryoblastic leukemia CMK-7 cell line.
2002 Sep-Oct
New propylamine oligopyrrole carboxamides linked to a heterocyclic or anthraquinone system: synthesis, DNA binding, topoisomerase I inhibition and cytotoxicity.
2003 Feb
Effects of 9,10 anthraquinone on ruminal fermentation, total-tract digestion, and blood metabolite concentrations in sheep.
2003 Jan
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
9,10-anthraquinone at concentration 100uM is able to impair β-amyloid peptides (Aβ) aggregation
Name Type Language
ANTHRAQUINONE
HSDB   ISO   MI  
Systematic Name English
ANTHRAQUINONE [HSDB]
Common Name English
9,10-ANTHRACENEDIONE
Systematic Name English
ANTHRADIONE
Common Name English
FLIGHT CONTROL
Brand Name English
MORKIT
Brand Name English
ANTHRAQUINONE [INCI]
Common Name English
ANTHRAQUINONE [IARC]
Common Name English
ANTHRAQUINONE [ISO]
Common Name English
9,10-ANTHRAQUINONE
Systematic Name English
KAWASAKI SAQ
Brand Name English
9,10-DIOXOANTHRACENE
Systematic Name English
NSC-7957
Code English
ANTHRAQUINONE [MI]
Common Name English
SAQ
Common Name English
HOELITE
Brand Name English
AVIPEL
Brand Name English
Classification Tree Code System Code
CFR 21 CFR 176.170
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
EPA PESTICIDE CODE 122701
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
NCI_THESAURUS C737
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
Code System Code Type Description
WIKIPEDIA
ANTHRAQUINONE
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
NSC
7957
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
MESH
C042834
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
HSDB
2074
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
ALANWOOD
anthraquinone
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
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EVMPD
SUB34652
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
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RXCUI
1482551
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY RxNorm
SMS_ID
100000128041
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
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FDA UNII
030MS0JBDO
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
NCI_THESAURUS
C26451
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
PUBCHEM
6780
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
CAS
84-65-1
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
CHEBI
40448
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
MERCK INDEX
m1949
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID3020095
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
DAILYMED
030MS0JBDO
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-549-0
Created by admin on Fri Dec 15 15:32:49 GMT 2023 , Edited by admin on Fri Dec 15 15:32:49 GMT 2023
PRIMARY