# Anthrone
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Anthrone
> Markdown URL: https://mediated.wiki/source/Anthrone.md
> Source: https://en.wikipedia.org/wiki/Anthrone
> Source revision: 1312262904
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{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](/source/Aromaticity) [ketone](/source/ketone). It is used for a common [cellulose](/source/cellulose) [assay](/source/assay) and in the colorimetric determination of carbohydrates.[{{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 }}]
[Derivatives](/source/Derivative_(chemistry)) 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](/source/Rhamnus_frangula)'', ''[Aloe ferox](/source/Aloe_ferox)'', ''[Rheum officinale](/source/Rheum_officinale)'', and ''[Cassia senna](/source/Cassia_senna)''.[{{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 }}] [Glycoside](/source/Glycoside)s of anthrone are also found in high amounts in [rhubarb](/source/rhubarb) leaves, and alongside concentrated amounts of [oxalic acid](/source/oxalic_acid) are the reason for the leaves being inedible.
==Synthesis and reactions==
Anthrone can be prepared from [anthraquinone](/source/anthraquinone) by reduction with [tin](/source/tin) or [copper](/source/copper).[{{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}}]
An alternative synthesis involves [cyclization](/source/cyclization) of ''o''-benzylbenzoic acid induced with [hydrogen fluoride](/source/hydrogen_fluoride).[{{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 }}]
thumb|center|400px|Anthrone syntheses
Anthrone condenses with [glyoxal](/source/glyoxal) to give, following dehydrogenation, [acedianthrone](/source/acedianthrone), a useful octacyclic pigment.[{{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}}]
thumb|center|314px|Tautomeric equilibrium for anthrone.
Anthrone is the more stable tautomer relative to the [anthrol](/source/anthrol) as has been established also by [X-ray crystallography](/source/X-ray_crystallography).[{{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 }}] The tautomeric equilibrium is estimated at 100 in aqueous solution. For the two other isomeric [anthrol](/source/anthrol)s, the tautomeric equilibrium is reversed: they are phenolic.[{{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.}}]
Anthrone undergoes nitration using conventional conditions for aromatic [nitration](/source/nitration), implying that it is the hydroxy tautomer that is the reactant.[{{cite journal |title=Nitroanthrone |journal=Organic Syntheses |date=1928 |volume=8 |page=78 |doi=10.15227/orgsyn.008.0078|author=Kurt H. Meyer}}]
==References==
{{reflist}}
Category:Aromatic ketones
Category:Anthracenes
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Adapted from the Wikipedia article [Anthrone](https://en.wikipedia.org/wiki/Anthrone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Anthrone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.