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			{{Short description|Yellow chemical compound: building block of many dyes}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 306671584
			| Watchedfields = changed
	| Name = Anthraquinone
			| verifiedrevid = 457132283
	| ImageFile = Anthraquinone acsv.svg
			| Name = 9,10-Anthraquinone<ref name=crc/>
	| ImageSize = 200px
	| ImageName = Anthraquinone		| ImageFile = Anthraquinone acsv.svg
	| IUPACName = Anthraquinone		| ImageFile1 = Anthraquinone molecule ball from xtal.png
			| ImageFile2= Anthraquinone powder.jpg
	| OtherNames = 9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, Hoelite, Morkit, Corbit
			| ImageSize2= 230px
			| PIN = Anthracene-9,10-dione<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=724 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
			| OtherNames = {{unbulletedlist | Anthraquinone | 9,10-Anthracenedione | Anthradione | 9,10-Anthrachinon | Anthracene-9,10-quinone | 9,10-Dihydro-9,10-dioxoanthracene | Hoelite | Morkit | Corbit }}
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
	| SMILES = O=C1c2ccccc2C(=O)c3ccccc13		| SMILES = O=C1c2ccccc2C(=O)c3ccccc13
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 6522		| ChemSpiderID = 6522
	| CASNo_Ref = {{cascite}}		| ChEBI_Ref = {{ebicite|changed|EBI}}
	| CASNo = 84-65-1		| ChEBI = 40448
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| RTECS =
			| ChEMBL = 55659
			| EC_number = 201-549-0
			| CASNo_Ref = {{cascite|correct|CAS}}
			| CASNo = 84-65-1
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| KEGG = C16207
			| Gmelin = 102870
			| Beilstein = 390030
			| PubChem = 6780
			| StdInChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H
			| StdInChIKey = RZVHIXYEVGDQDX-UHFFFAOYSA-N
			| RTECS = CB4725000
			| UNNumber = 3143
			| UNII = 030MS0JBDO
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	|C=14|H=8|O=2		| C=14 | H=8 | O=2
	| Appearance = yellow or light gray to gray-green solid		| Appearance = Yellow solid
	| Density =		| Density = 1.438{{nbsp}}g/cm<sup>3</sup><ref name=crc/>
	| Solubility = Insoluble		| Solubility = Insoluble
	| MeltingPt = 286 °C		| MeltingPtC = 284.8
			| MeltingPt_ref = <ref name=crc>{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293|page=3.28}}</ref>
	| BoilingPt = 379.8 °C
			| BoilingPtC = 377
			| BoilingPt_ref = <ref name=crc/>
	}}		}}
	| Section7 = {{Chembox Hazards		| Section7 = {{Chembox Hazards
	| MainHazards =		| MainHazards = possible carcinogen
	| FlashPt = 185°C		| FlashPtC = 185
	| RPhrases = {{R36/37/38}}		| GHSPictograms = {{GHS08}}
	| SPhrases =		| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|350}}
			| PPhrases = {{P-phrases|201|202|281|308+313|405|501}}
	}}		}}
	| Section8 = {{Chembox Related		| Section8 = {{Chembox Related
	| OtherCpds = ],</br> ]		| OtherCompounds = ],<br> ]
	}}		}}
	}}		}}
			'''Anthraquinone''', also called '''anthracenedione''' or '''dioxoanthracene''', is an ] ] with formula {{chem|C|14|H|8|O|2}}. Several ]s exist but these terms usually refer to 9,10-anthraquinone (]: 9,10-dioxoanthracene) wherein the ] groups are located on the central ring. It is used as a digester additive to ] for papermaking. Many ] are generated by organisms or synthesised industrially for use as ], pharmaceuticals, and ]. Anthraquinone is a yellow, highly crystalline solid, poorly ] in ] but soluble in hot organic solvents. It is almost completely insoluble in ] near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral ].
	'''Anthraquinone''' ('''9,10-dioxoanthracene''') is an ] ]. It is a derivative of ]. It has the appearance of yellow or light gray to gray-green solid crystalline powder.
			==Synthesis==
	Its other names are 9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, and trade names Hoelite, Morkit, Corbit, and others.
			There are several current industrial methods to produce 9,10-anthraquinone:
			# The oxidation of ]. ] is the typical oxidant.
			# The ] of ] and ] in presence of ]. o-Benzoylbenzoic acid is an intermediate. This reaction is useful for producing substituted ].
			# The ] of ] and ] followed by oxidative dehydrogenation.
			# The acid-catalyzed dimerization of ] to give a 1,3-diphenylbutene, which then can be transformed to the anthraquinone.<ref name=Ullmann>{{ Ullmann | author = Vogel, A. | title = Anthraquinone | doi = 10.1002/14356007.a02_347 }}</ref> This process was pioneered by ].
			It also arises via the Rickert–Alder reaction, a ].
	==Physical properties==
	It is ] in ] but dissolves in ], ] and ]. It is chemically fairly stable under normal conditions.
			==Reactions==
	==Natural occurrences==
			Hydrogenation gives ] (anthrahydroquinone). Reduction with copper gives ].<ref>{{cite journal|doi= 10.15227/orgsyn.014.0004|title= Benzanthrone|journal= Organic Syntheses|year= 1934|volume= 14|pages= 4|first1=L. C. |last1= Macleod|first2=C. F. H.|last2=Allen}}</ref> Sulfonation with sulfuric acid gives anthroquinone-1-sulfonic acid,<ref>{{cite journal|doi= 10.15227/orgsyn.018.0072|title= Potassium Anthraquinone-α-Sulfonate|journal= Organic Syntheses|year= 1938|volume= 18|pages= 72|first1=W. J. |last1=Scott|first2=C. F. H.|last2=Allen}}</ref> which reacts with sodium chlorate to give 1-chloroanthaquinone.<ref>{{cite journal|doi= 10.15227/orgsyn.018.0015|title= α-Chloroanthraquinone|journal= Organic Syntheses|year= 1938|volume= 18|pages= 15|first1=W. J. |last1=Scott|first2=C. F. H.|last2=Allen}}</ref>
	Anthraquinones naturally occur in some plants (eg. ], ], ], and ]), ], ]s, and ]s, where they serve as a basic skeleton for their pigments. Natural anthraquinone derivatives tend to have ] effects.
	==Chemistry==		==Applications==
			{{see also|Anthraquinones}}
	There are several ways to obtain anthraquinone:
	* Oxidation of ]
	* Condensation of ] with ] in presence of AlCl<sub>3</sub> (]). The resulting o-benzoylbenzoic acid then undergoes cyclization, forming anthraquinone.
	* ] (from ] and a buta-1,3-diene followed by oxidation)
	* Retro-DA reaction: the ].
			===Digester additive in papermaking===
	In a classic ] called the '''Bally-Scholl synthesis''' (1905), anthraquinone ] with ] forming ]<ref>{{OrgSynth | title = Benzathrone | author = L. C. Macleod and C. F. H. Allen | collvol = 2 | collvolpages = 62 | year = 1943 | prep = CV2P0062}}</ref>. In this reaction the quinone is first ] with ] metal in ] (converting one ] group into a ] group) after which the glycerol is added.
			9,10-Anthraquinone is used as a digester additive in production of ] by ]ne processes, like the ], the alkaline ] or the ] processes. The anthraquinone is a ] ]. The reaction mechanism may involve ] (SET).<ref>{{Cite thesis | first = J. C. | last = Samp | title = A comprehensive mechanism for anthraquinone mass transfer in alkaline pulping | year = 2008 | page = 30 | institution = Georgia Institute of Technology | hdl=1853/24767 }}</ref> The anthraquinone oxidizes the reducing end of polysaccharides in the pulp, i.e., ] and ], and thereby protecting it from alkaline degradation (peeling). The anthraquinone is reduced to ] which then can react with ]. The lignin is degraded and becomes more watersoluble and thereby more easy to wash away from the pulp, while the anthraquinone is regenerated. This process gives an increase in yield of pulp, typically 1–3% and a reduction in ].<ref>{{ cite book | editor = Goyal, G. C. | last1 = Sturgeoff | first = L. G. | last2 = Pitl | first2 = Y. | chapter = Low Kappa Pulping without Capital Investment | title = Anthraquinone Pulping | publisher = TAPPI Press | pages = 3–9 | orig-year = 1993 | year = 1997 | isbn = 0-89852-340-0 }}</ref>
			=== Hydrogen Peroxide Production ===
	:]
			2-Alkyl-9,10-Anthroquinones are used as a catalyst in the ] for the production of hydrogen peroxide. This process is the dominant industrial method of hydrogen peroxide production.<ref>{{Cite journal |last=Campos-Martin |first=Jose M. |last2=Blanco-Brieva |first2=Gema |last3=Fierro |first3=Jose L. G. |date=2006 |title=Hydrogen Peroxide Synthesis: An Outlook beyond the Anthraquinone Process |url=https://onlinelibrary.wiley.com/doi/10.1002/anie.200503779 |journal=Angewandte Chemie International Edition |language=en |volume=45 |issue=42 |pages=6962–6984 |doi=10.1002/anie.200503779 |issn=1521-3773}}</ref>
			===Niche uses===
	==Industrial applications==
			9,10-anthraquinone is used as a bird repellant on seeds, and as a gas generator in satellite balloons.<ref>{{Cite web |url=http://www.americanheritage.com/articles/magazine/it/2007/1/2007_1_38.shtml |title=www.americanheritage.com |access-date=2009-09-22 |archive-url=https://web.archive.org/web/20090609235239/http://www.americanheritage.com/articles/magazine/it/2007/1/2007_1_38.shtml |archive-date=2009-06-09 |url-status=dead }}</ref> It has also been mixed with lanolin and used as a wool spray to protect sheep flocks against ] attacks in New Zealand.<ref>{{cite news |last=Dudding |first=Adam |date=29 July 2012 |title=How to solve a problem like a kea |url=http://www.stuff.co.nz/science/7370200/How-to-solve-a-problem-like-the-kea |newspaper=Sunday Star Times |location=New Zealand |access-date=11 November 2014}}</ref>
	* Anthraquinone is used in production of ], such as ].
	* Many natural ]s are derivatives of anthraquinone.
	* Anthraquinone may be used as a ] in production of ] by the ] or ]es.
	* Another use is as a bird repellant on seeds.
	* As a gas generator in Satellite balloons
	* A derivative of anthraquinone called 2-ethylanthraquinone is used to produce ] commercially.
	:]{{clear-left}}
	==Medical uses==		==Other isomers==
			Several other isomers of anthraquinone exist, including the 1,2-, 1,4-, and 2,6-anthraquinones. They are of minor importance compared to 9,10-anthraquinone.
	Anthraquinone is used as a ]. Prolonged use and ] leads to ].<ref>{{cite journal |author=Müller-Lissner SA |title=Adverse effects of laxatives: fact and fiction |journal=Pharmacology |volume=47 Suppl 1 |issue= |pages=138–45 |year=1993 |pmid=8234421 |doi=10.1159/000139853}}</ref><ref name="pmid3280173">{{cite journal |author=Moriarty KJ, Silk DB |title=Laxative abuse |journal=Dig Dis |volume=6 |issue=1 |pages=15–29 |year=1988 |pmid=3280173 |doi= 10.1159/000171181|url=}}</ref>
	==External links==		==Safety==
			Anthraquinone has no recorded {{LD50}}, probably because it is so insoluble in water.
	*
	*
			In terms of metabolism of substituted anthraquinones, the enzyme encoded by the gene ] has glucuronidase activity with many substrates including anthraquinones.<ref name="pmid1339448">{{ cite journal |author1= Ritter, J. K. |author2=Chen, F. |author3=Sheen, Y. Y. |author4=Tran, H. M. |author5=Kimura, S. |author6=Yeatman, M. T. |author7=Owens, I. S. | title = A Novel Complex Locus UGT1 Encodes Human Bilirubin, Phenol, and other UDP-Glucuronosyltransferase Isozymes with Identical Carboxyl Termini | journal = Journal of Biological Chemistry | year = 1992 | volume = 267 | issue = 5 | pages = 3257–3261 |doi=10.1016/S0021-9258(19)50724-4 | pmid = 1339448 | url = http://www.jbc.org/content/267/5/3257.full.pdf |doi-access=free }}</ref>
			== See also ==
			* ]
			* ]
			* ]
			* ]
	==References==		==References==
	{{reflist}}		{{reflist}}
			==External links==
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