Anthrone: Difference between revisions

| Watchedfields = changed

| verifiedrevid = 443392881

| PIN = Anthracen-9(10''H'')-one

| OtherNames = {{bulletedlist|Carbothrone| 9-Oxoanthracene}}

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = FP0FJ7K744

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChemSpiderID =6751

|Section2={{Chembox Properties

| C=14|H=10|O=1

| Density =

| MeltingPtC = 155 to 158

| MeltingPt_notes =

| BoilingPtC =

| BoilingPt_notes =

|Section3={{Chembox Hazards

| AutoignitionPt =

'''Anthrone''' is a tricyclic [[Aromaticity|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>

[[Derivative (chemistry)|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 |last=Niaz |first=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}}</ref> [[Glycoside]]s 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}}</ref>

[[File:Anthrone synthesis.svg|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>

==Tautomer==

[[image:Anthrol-AnthroneEq.svg|thumb|center|314px|Tautomeric equilibrium for anthrone.]]

Anthrone is the more stable tautomer relative to the [[anthrol]]. The tautomeric equilibrium is estimated at 100 in aqueous solution. For the two other isomeric anthrols, the tautomeric equilibrium is reversed.<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>

==References==

{{reflist}}

[[Category:Aromatic ketones]]

[[Category:Anthracenes]]