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=CC=CC=C2C(=O)C3=CC=CC=C13

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

Molecular Formula C14H8O2
Molecular Weight 208.2121
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Primary quinone (QA) binding site of bacterial photosynthetic reaction centers: mutations at residue M265 probed by FTIR spectroscopy.
2003-04-15
Identification of natural dyes in archeological Coptic textiles by liquid chromatography with diode array detection.
2003-03-14
Constitutional isomers of Reactive Blue 2 - selective P2Y-receptor antagonists?
2003-03
Decolorization of structurally different synthetic dyes using cobalt(II)/ascorbic acid/hydrogen peroxide system.
2003-03
Kinetic and docking studies of the interaction of quinones with the quinone reductase active site.
2003-02-25
New propylamine oligopyrrole carboxamides linked to a heterocyclic or anthraquinone system: synthesis, DNA binding, topoisomerase I inhibition and cytotoxicity.
2003-02
Inhibition of protein kinase CK2 by anthraquinone-related compounds. A structural insight.
2003-01-17
Spectral investigations on 1,5-dipiperidino anthraquinone.
2003-01-15
First linear alignment of five C-Se...O...Se-C atoms in anthraquinone and 9-(methoxy)anthracene bearing phenylselanyl groups at 1,8-positions.
2003-01-07
Biochemical and genetic characterization of PpcA, a periplasmic c-type cytochrome in Geobacter sulfurreducens.
2003-01-01
Effects of 9,10 anthraquinone on ruminal fermentation, total-tract digestion, and blood metabolite concentrations in sheep.
2003-01
Pharmacokinetic analysis of rhein in Rheum undulatum L.
2003-01
Differential ability of cytostatics from anthraquinone group to generate free radicals in three enzymatic systems: NADH dehydrogenase, NADPH cytochrome P450 reductase, and xanthine oxidase.
2003
Studies toward the total synthesis of mumbaistatin, a highly potent glucose-6-phosphate translocase inhibitor. Synthesis of a mumbaistatin analogue.
2002-12-27
Bichromophoric perylene derivatives: energy transfer from non-fluorescent chromophores.
2002-12-16
Effects of polyphenolic anthrone derivatives, resistomycin and hypercin, on apoptosis in human megakaryoblastic leukemia CMK-7 cell line.
2002-11-21
Synthesis of symmetrical 1,5-bis-thio-substituted anthraquinones for cytotoxicity in cultured tumor cells and lipid peroxidation.
2002-11
Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin.
2002-10-31
The charge conduction properties of DNA holliday junctions depend critically on the identity of the tethered photooxidant.
2002-10-23
Inducible nitric oxide synthase inhibitors of Chinese herbs III. Rheum palmatum.
2002-10
Long-range oxidative damage to DNA: protection of guanines by a nonspecifically bound disulfide.
2002-09-25
Draculone, a new anthraquinone pigment from the tropical lichen Melanotheca cruenta.
2002-09-21
long-range charge transport in duplex DNA: anthraquinone sensitization results are independent of terminal ionic distribution.
2002-09-18
Thermovenabulum ferriorganovorum gen. nov., sp. nov., a novel thermophilic, anaerobic, endospore-forming bacterium.
2002-09
Effect of salicylic acid, methyl jasmonate, ethephon and cantharidin on anthraquinone production by Rubia cordifolia callus cultures transformed with the rolB and rolC genes.
2002-08-28
Toward the rational design of protein kinase casein kinase-2 inhibitors.
2002-08-23
A 9,10-anthraquinone derivative having two propenyl arms as a neutral ionophore for highly selective and sensitive membrane sensors for copper(II) ion.
2002-08
Diacerhein and rhein prevent interleukin-1beta-induced nuclear factor-kappaB activation by inhibiting the degradation of inhibitor kappaB-alpha.
2002-07
Determination of anthraquinone in technical material, formulations, and lettuce by high performance liquid chromatography.
2002-06-19
Highly selective amorphous Ni-Cr-B catalyst in 2-ethylanthraquinone hydrogenation to 2-ethylanthrahydroquinone.
2002-06-07
Caffeine, quercetin and alizarin stimulate the exhalation of metabolic products of [14C]-N-nitrosodiethylamine in mice.
2002-06
Studies on the photostability and phototoxicity of aloe-emodin, emodin and rhein.
2002-06
Cytotoxic anthraquinone derivatives from Picramnia antidesma.
2002-06
Acute lethal toxicity of environmental pollutants to aquatic organisms.
2002-06
Luminescence and structural comparisons of strong-acid sensor molecules. 2.
2002-05-31
Synthesis of 11-hydroxyl O-methylsterigmatocystin and the role of a cytochrome P-450 in the final step of aflatoxin biosynthesis.
2002-05-15
Cytotoxicity of rhein, the active metabolite of sennoside laxatives, is reduced by multidrug resistance-associated protein 1.
2002-05-06
Antifeedant activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F.
2002-05
Antiplasmodial activity of naphthoquinones and one anthraquinone from Stereospermum kunthianum.
2002-05
Photochemical synthesis of aldehydes in the solid phase.
2002-04-19
Two new naphthalene and anthraquinone derivatives from Asphodelus tenuifolius.
2002-04
Steric and electrostatic effects in dye-cellulose interactions by the MTD and CoMFA approaches.
2002-03
Decolorization of textile dyes by laccases from a newly isolated strain of Trametes modesta.
2002-03
Anthrapyridones, a novel group of antitumour non-cross resistant anthraquinone analogues. Synthesis and molecular basis of the cytotoxic activity towards K562/DOX cells.
2002-03
Enhanced clearance of topoisomerase I inhibitors from human colon cancer cells by glucuronidation.
2002-02-15
Structure of acid-stable carmine.
2002-02
Excited state intramolecular redox reaction of 2-(hydroxymethyl)anthraquinone in aqueous solution.
2002-01-21
Kinetics and inhibition during the decolorization of reactive anthraquinone dyes under methanogenic conditions.
2002
[Studies on the anthraquinones of Cassia siamea].
2001-07
Examination of the best pressure range for ion/molecule reactions of anthraquinones in an external source ion trap mass spectrometer.
2001-04
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:00:42 GMT 2025
Edited
by admin
on Mon Mar 31 18:00:42 GMT 2025
Record UNII
030MS0JBDO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANTHRAQUINONE
HSDB   ISO   MI  
Systematic Name English
AVIPEL
Preferred 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 [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
Classification Tree Code System Code
CFR 21 CFR 176.170
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
EPA PESTICIDE CODE 122701
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
NCI_THESAURUS C737
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
Code System Code Type Description
WIKIPEDIA
ANTHRAQUINONE
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
NSC
7957
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
MESH
C042834
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
HSDB
2074
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
ALANWOOD
anthraquinone
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
EVMPD
SUB34652
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
RXCUI
1482551
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY RxNorm
SMS_ID
100000128041
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
FDA UNII
030MS0JBDO
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
NCI_THESAURUS
C26451
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
PUBCHEM
6780
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
CAS
84-65-1
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
CHEBI
40448
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
MERCK INDEX
m1949
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID3020095
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
DAILYMED
030MS0JBDO
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-549-0
Created by admin on Mon Mar 31 18:00:42 GMT 2025 , Edited by admin on Mon Mar 31 18:00:42 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY