{{chembox | Watchedfields = changed | verifiedrevid = 443392881 | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = Anthrone.png | ImageSize = 180 | ImageName = Skeletal formula | ImageFile1 = Anthrone-3D-balls.png | ImageSize1 = 210 | ImageName1 = Ball-and-stick model | PIN = Anthracen-9(10''H'')-one | OtherNames = {{bulletedlist|Carbothrone| 9-Oxoanthracene}} |Section1={{Chembox Identifiers | InChIKey = RJGDLRCDCYRQOQ-UHFFFAOYAA | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 124440 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8H,9H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RJGDLRCDCYRQOQ-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 90-44-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = FP0FJ7K744 | PubChem = 7018 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 33835 | SMILES = O=C2c1c(cccc1)Cc3c2cccc3 | InChI = 1/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8H,9H2 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID =6751 }} |Section2={{Chembox Properties | C=14|H=10|O=1 | Appearance = White to light yellow needles | Density = | MeltingPtC = 155 to 158 | MeltingPt_notes = | BoilingPtC = | BoilingPt_notes = | Solubility = Insoluble }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Anthrone''' is a tricyclic aromatic ketone. It is used for a common cellulose assay and in the colorimetric determination of carbohydrates.<ref>{{cite journal | title = Determination of Yeast Carbohydrates with the Anthrone Reagent | journal = Nature | volume = 170 | pages = 626–627 | year = 1952 | doi = 10.1038/170626a0 | author = Trevelyan, W. E. | pmid = 13002392 | last2 = Forrest | first2 = RS | last3 = Harrison | first3 = JS | issue = 4328| bibcode = 1952Natur.170..626T| s2cid = 4184596 }}</ref>
Derivatives of anthrone are used in pharmacy as laxative. They stimulate the motion of the colon and reduce water reabsorption. Some anthrone derivatives can be extracted from a variety of plants, including ''Rhamnus frangula'', ''Aloe ferox'', ''Rheum officinale'', and ''Cassia senna''.<ref>{{Citation |last1=Niaz |first1=Kamal |title=Chapter 3 - Analysis of polyphenolics |date=2020-01-01 |work=Recent Advances in Natural Products Analysis |pages=39–197 |editor-last=Sanches Silva |editor-first=Ana |url=https://www.sciencedirect.com/science/article/pii/B9780128164556000032 |access-date=2024-06-01 |publisher=Elsevier |doi=10.1016/b978-0-12-816455-6.00003-2 |isbn=978-0-12-816455-6 |last2=Khan |first2=Fazlullah |editor2-last=Nabavi |editor2-first=Seyed Fazel |editor3-last=Saeedi |editor3-first=Mina |editor4-last=Nabavi |editor4-first=Seyed Mohammad|url-access=subscription }}</ref> Glycosides of anthrone are also found in high amounts in rhubarb leaves, and alongside concentrated amounts of oxalic acid are the reason for the leaves being inedible.
==Synthesis and reactions== Anthrone can be prepared from anthraquinone by reduction with tin or copper.<ref>{{cite journal |doi=10.15227/orgsyn.014.0004|title=Benzanthrone|journal=Organic Syntheses|year=1934|volume=14|page=4|first1=L. C.|last1=Macleod|first2=C. F. H.|last2=Allen}}</ref>
An alternative synthesis involves cyclization of ''o''-benzylbenzoic acid induced with hydrogen fluoride.<ref>{{cite journal|last1=Fieser|first1=Louis F.|last2=Hershberg|first2=E. B.|title=Inter- and Intramolecular Acylations with Hydrogen Fluoride|journal=Journal of the American Chemical Society|date=May 1939|volume=61|issue=5|pages=1272–1281|doi=10.1021/ja01874a079 |bibcode=1939JAChS..61.1272F }}</ref>
thumb|center|400px|Anthrone syntheses
Anthrone condenses with glyoxal to give, following dehydrogenation, acedianthrone, a useful octacyclic pigment.<ref name=UllmannDye>{{Ullmann | last1= Bien|first1=H.-S.| last2=Stawitz |first2=J.| last3= Wunderlich|first3=K. | title = Anthraquinone Dyes and Intermediates | doi = 10.1002/14356007.a02_355|year=2005}}</ref>
thumb|center|314px|Tautomeric equilibrium for anthrone. Anthrone is the more stable tautomer relative to the anthrol as has been established also by X-ray crystallography.<ref>{{cite journal |last1=Lian |first1=Jian-Jou |last2=Lin |first2=Chung-Chang |last3=Chang |first3=Hsu-Kai |last4=Chen |first4=Po-Chiang |last5=Liu |first5=Rai-Shung |title=Thermal and Metal-Catalyzed Cyclization of 1-Substituted 3,5-Dien-1-ynes via a [1,7]-Hydrogen Shift: Development of a Tandem Aldol Condensation−Dehydration and Aromatization Catalysis between 3-En-1-yn-5-al Units and Cyclic Ketones |journal=Journal of the American Chemical Society |date=2006 |volume=128 |issue=30 |pages=9661–9667 |doi=10.1021/ja061203b |pmid=16866518 |bibcode=2006JAChS.128.9661L }}</ref> The tautomeric equilibrium is estimated at 100 in aqueous solution. For the two other isomeric anthrols, the tautomeric equilibrium is reversed: they are phenolic.<ref>{{cite journal|doi=10.1021/jo052615q|pmid=16674042|title=Tautomeric Equilibria and Pi Electron Delocalization for Some Monohydroxyarenes ''Quantum'' Chemical Studies|journal=The Journal of Organic Chemistry|volume=71|issue=10|pages=3727–3736|year=2006|last1=Ośmiałowski|first1=Borys|last2=Raczyńska|first2=Ewa D.|last3=Krygowski|first3=Tadeusz M.}}</ref>
Anthrone undergoes nitration using conventional conditions for aromatic nitration, implying that it is the hydroxy tautomer that is the reactant.<ref>{{cite journal |title=Nitroanthrone |journal=Organic Syntheses |date=1928 |volume=8 |page=78 |doi=10.15227/orgsyn.008.0078|author=Kurt H. Meyer}}</ref>
==References== {{reflist}}
Category:Aromatic ketones Category:Anthracenes