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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Acridon</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
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<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span class="mw-default-size" typeof="mw:File"></span>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
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<td style="width:33%;">Name
</td>
<td>Acridon
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>9(10<i>H</i>)-Acridon</li>
<li>9,10-Dihydro-9-oxoacridin</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>13</sub>H<sub>9</sub>NO
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>gelber Feststoff<sup id="cite_ref-Thermofisher_1-0" class="reference"><a href="#cite_note-Thermofisher-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sigma_2-0" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
</th></tr>
<tr>
<td colspan="2" style="padding:0;">
<table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);">
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<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=578-95-0">578-95-0</a><span class="editoronly" style="display:none;"></span>
</td>
<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
<tr>
<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a>
</td>
<td colspan="2">209-434-7
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.008.578">100.008.578</a>
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/2015">2015</a>
</td></tr>
<tr>
<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.10188539.html">10188539</a>
</td></tr>
<tr>
<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q342721" class="extiw external" title="d:Q342721">Q342721</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>195,22 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>fest<sup id="cite_ref-Sigma_2-1" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>360–362 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-Thermofisher_1-1" class="reference"><a href="#cite_note-Thermofisher-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
<tbody><tr>
<td colspan="2" style="text-align:center"><b><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-Sigma_2-2" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table>
<p>
</p>
</td></tr>
<tr>
<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>
</td>
<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i><sup id="cite_ref-Sigma_2-3" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td></tr>
</tbody></table>
</td></tr>
<tr>
<td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Acridon</b> (9(10<i>H</i>)-Acridon) ist strukturell mit seinem Stammkörper <a href="Acridin" title="Acridin">Acridin</a> und dem <a href="Polycyclische_aromatische_Kohlenwasserstoffe" title="Polycyclische aromatische Kohlenwasserstoffe">polycyclischen aromatischen Kohlenwasserstoff</a> <a href="Anthracen" title="Anthracen">Anthracen</a> verwandt, besitzt jedoch im Unterschied zu diesem als zentralen Sechsring ein <a href="Heteroaromaten" title="Heteroaromaten">heteroaromatisches</a> <a href="4-Pyridon" title="4-Pyridon">4-Pyridon</a>. Die Acridonstruktur kann auch aus der <a href="Chinacridon" title="Chinacridon">Chinacridon</a>-Struktur abgeleitet werden, indem aus dieser ein 4-Pyridon-Ring zusammen mit einem anschließenden peripheren Ring entfernt wird.
</p>
<div class="mw-heading mw-heading2"><h2 id="Geschichte">Geschichte</h2></div>
<p>Nach einer Publikation von Karl Drechsler, einem Studenten von <a href="Guido_Goldschmiedt" title="Guido Goldschmiedt">Guido Goldschmiedt</a> an der k.u.k. <a href="Universit%C3%A4t_Wien" title="Universität Wien">Universität Wien</a>, entdeckte Moriz Freund den Stoff 1896 bei Versuchen an der <a href="Universit%C3%A4t_Prag" class="mw-redirect" title="Universität Prag">Universität Prag</a>.<sup id="cite_ref-DOI10.1007/BF01519382_3-0" class="reference"><a href="#cite_note-DOI10.1007/BF01519382-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Drechsler konnte den Stoff dann in größeren Mengen herstellen und in der Folge auch näher untersuchen.
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>Acridon<a href="Derivat_(Chemie)" title="Derivat (Chemie)">derivate</a> lassen sich als <a href="Fluoreszenz" title="Fluoreszenz">Fluoreszenz</a>-Sonde<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> in der <a href="Molekularbiologie" title="Molekularbiologie">Molekularbiologie</a> oder zur Messung der Lewis-Acidität von <a href="Metallion#Metallionen" class="mw-redirect" title="Metallion">Metallionen</a>-Salzen<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> einsetzen. In der <a href="Medizin" title="Medizin">Medizin</a> sind <a href="Acridon-Alkaloide" title="Acridon-Alkaloide">Acridon-Alkaloide</a> als <a href="Wirkstoff" title="Wirkstoff">Wirkstoff</a> gegen <a href="Krebs_(Medizin)" title="Krebs (Medizin)">Krebs</a><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> und <a href="Malaria" title="Malaria">Malaria</a><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> geeignet.
</p>
<div class="mw-heading mw-heading2"><h2 id="Synthese">Synthese</h2></div>
<p>Eine mögliche Laborsynthese von Acridon erfolgt durch <a href="Jourdan-Ullmann-Reaktion" title="Jourdan-Ullmann-Reaktion">Jourdan-Ullmann-Kupplung</a> von <i>ortho</i>-<a href="Chlorbenzoes%C3%A4uren" title="Chlorbenzoesäuren">Chlorbenzoesäure</a> mit <a href="Anilin" title="Anilin">Anilin</a> zu <a href="N-Phenylanthranils%C3%A4ure" title="N-Phenylanthranilsäure"><i>N</i>-Phenylanthranilsäure</a>, gefolgt von einer <a href="Schwefels%C3%A4ure" title="Schwefelsäure">schwefelsäurevermittelten</a> <a href="Cyclisierung" title="Cyclisierung">Zyklisierung</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Thermofisher-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Thermofisher_1-0">a</a></sup> <sup><a href="#cite_ref-Thermofisher_1-1">b</a></sup></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.thermofisher.com/order/catalog/product/400250250?SID=srch-srp-400250250">9(10H)-Acridone</a></span> bei <i><a href="Thermo_Fisher_Scientific" title="Thermo Fisher Scientific">Thermo Fisher Scientific</a></i>, abgerufen am 13. Oktober 2023.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Sigma-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_2-0">a</a></sup> <sup><a href="#cite_ref-Sigma_2-1">b</a></sup> <sup><a href="#cite_ref-Sigma_2-2">c</a></sup> <sup><a href="#cite_ref-Sigma_2-3">d</a></sup></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/ALDRICH/150215">9(10H)-Acridanone</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 19. März 2025 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/150215?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-DOI10.1007/BF01519382-3"><span class="mw-cite-backlink"><a href="#cite_ref-DOI10.1007/BF01519382_3-0">↑</a></span> <span class="reference-text">Karl Drechsler: <a rel="nofollow" class="external text" href="https://anno.onb.ac.at/cgi-content/anno-plus?aid=mch&datum=1914&size=45&page=667"><i>Über eine bei der Einwirkung von Aluminiumchlorid auf o-Nitrobenzylchlorid und Benzol entstehende Base C<sub>13</sub>H<sub>9</sub>NO.</i></a> In: <i>Monatshefte für Chemie.</i> 35, 1914, S. 533, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1007/BF01519382">10.1007/BF01519382</a></span>.</span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">J. A. Smith, R. M. West, M. Allen: <i>Acridones and Quinacridones: Novel Fluorophores for Fluorescence Lifetime Studies.</i> In: <i><a href="Journal_of_Fluorescence" title="Journal of Fluorescence">Journal of Fluorescence</a></i> 14, 2004, S. 151–171; <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1023/B%3AJOFL.0000016287.56322.eb">10.1023/B:JOFL.0000016287.56322.eb</a></span>.</span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">S. H. Mihindukulasuriya, T. K. Morcone, L. B. McGown: <i>Characterization of acridone dyes for use in four-decay detection in DNA sequencing.</i> In: <i><a href="Electrophoresis" title="Electrophoresis">Electrophoresis</a></i> 24, 2003, S. 20–25; <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/elps.200390017">10.1002/elps.200390017</a></span>.</span>
</li>
<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">S. Fukuzumi, K. Ohkubo: <i>Fluorescence Maxima of 10-Methylacridone-Metal Ion Salt Complexes: A Convenient and Quantitative Measure of Lewis Acidity of Metal Ion Salts.</i> In: <i><a href="Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">J. Am. Chem. Soc.</a></i> 124, 2002, S. 10270–10271; <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1021/ja026613o">10.1021/ja026613o</a></span>.</span>
</li>
<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">N. Guilbaud, S. Leonce, F. Tillequin, M. Koch, J. A. Hickman, A. Pierre: <i>Acronycine derivatives as promising antitumor agents.</i> In: <i><a href="Anti-Cancer_Drugs" title="Anti-Cancer Drugs">Anti-Cancer Drugs</a></i> 13, 2002, S. 445–449.</span>
</li>
<li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">L. K. Basco, S. Mitaku, A. L. Skaltsounis, N. Ravelomanantsoa, F. Tillequin, M. Koch, J. Le Bras: <i>In Vitro Activities of Furoquinoline and Acridone Alkaloids against Plasmodium falciparum.</i> In: <i><a href="Antimicrobial_Agents_and_Chemotherapy" title="Antimicrobial Agents and Chemotherapy">Antimicrob. Agents Chemother.</a></i> 38, 1994, S. 1169–1171; <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC188171/">PMC 188171</a> (freier Volltext).</span>
</li>
<li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text"><cite style="font-style:italic">ACRIDONE</cite>. In: <cite style="font-style:italic">Organic Syntheses</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>19</span>, 1939, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>6</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.15227/orgsyn.019.0006">10.15227/orgsyn.019.0006</a></span> (<a rel="nofollow" class="external text" href="http://orgsyn.org/demo.aspx?prep=CV2P0015">orgsyn.org</a> [abgerufen am 19. März 2025]).<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:Acridon&rft.atitle=ACRIDONE&rft.btitle=Organic+Syntheses&rft.date=1939&rft.doi=10.15227%2Forgsyn.019.0006&rft.genre=book&rft.pages=6&rft.volume=19" style="display:none"> </span></span>
</li>
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