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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Rubiadin</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">
<tbody><tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
</th></tr>
<tr>
<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span 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>Rubiadin
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>1,3-Dihydroxy-2-methyl-9,10-anthracendion</li>
<li>1,3-Dihydroxy-2-methylanthrachinon</li>
<li><a href="Colour_Index" title="Colour Index">C.I.</a> Natural Red 8</li>
<li>C.I. 75350</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>15</sub>H<sub>10</sub>O<sub>4</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>gelber bis oranger Feststoff<sup id="cite_ref-Sigma_1-0" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-W._Karrer_2-0" class="reference"><a href="#cite_note-W._Karrer-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);">
<tbody><tr>
<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td>
<ul><li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=117-02-2">117-02-2</a><span class="editoronly" style="display:none;"></span></li>
<li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=12640-73-2">12640-73-2</a><span class="editoronly" style="display:none;"></span> unspezifiziert Natural Red 8<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>S 1<span class="cite-bracket">]</span></a></sup></li></ul>
</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> (<a href="EG-Nummer#Listennummern" title="EG-Nummer">Listennummer</a>)
</td>
<td colspan="2">683-093-6
</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/100.208.613">100.208.613</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/124062">124062</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.110563.html">110563</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/Q15633911" class="extiw external" title="d:Q15633911">Q15633911</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>254,24 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_1-1" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>290 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-Sigma_1-2" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<p>löslich in organischen Lösungsmitteln wie <a href="DMSO" class="mw-redirect" title="DMSO">DMSO</a> und <a href="Dimethylformamid" title="Dimethylformamid">Dimethylformamid</a><sup id="cite_ref-caymanchem.com_4-0" class="reference"><a href="#cite_note-caymanchem.com-4"><span class="cite-bracket">[</span>3<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_1-3" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<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><span typeof="mw:File"><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien#Übersicht:_EU-Gefahrensymbole,_UN/GHS-Gefahrenpiktogramme,_UN/ADR-Gefahrensymbole" title="07 – Achtung"></a></span>
</td>
<td><span typeof="mw:File"><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien#Übersicht:_EU-Gefahrensymbole,_UN/GHS-Gefahrenpiktogramme,_UN/ADR-Gefahrensymbole" title="08 – Gesundheitsgefährdend"></a></span>
</td></tr></tbody></table>
<p><b>Achtung</b>
</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><a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Gesundheitsschädlich bei Verschlucken.">302</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Kann vermutlich Krebs erzeugen (Expositionsweg angeben, sofern schlüssig belegt ist, dass diese Gefahr bei keinem anderen Expositionsweg besteht).">351</span></span></a>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.">202</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Nach Gebrauch … gründlich waschen.
(Die vom Gesetzgeber offen gelassene Einfügung ist vom Inverkehrbringer zu ergänzen)">264</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Schutzhandschuhe/Schutzkleidung/Augenschutz/Gesichtsschutz/Gehörschutz/… tragen.
(Geänderter Text seit Inkraftreten der „12. Anpassung an den Technischen Fortschritt“ am 17. Oktober 2020)">280</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Bei Verschlucken: Bei Unwohlsein Giftinformationszentrum / Arzt / … anrufen.">301+312</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Bei Exposition oder falls betroffen: Ärztlichen Rat Einholen / ärztliche Hilfe hinzuziehen.">308+313</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Unter Verschluss aufbewahren.">405</span></span></a><sup id="cite_ref-Sigma_1-4" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<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>Rubiadin</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Gruppe der <a href="Anthrachinonfarbstoffe" title="Anthrachinonfarbstoffe">Anthrachinonfarbstoffe</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Geschichte">Geschichte</h2></div>
<p>Obwohl Rubiadin erstmals 1853 von <a href="Edward_Schunck" title="Edward Schunck">Edward Schunck</a> aus der <a href="Krappwurzel" class="mw-redirect" title="Krappwurzel">Krappwurzel</a> <i>Rubia tinctoria</i> isoliert wurde, gelang es Schunck und <a href="Leon_Marchlewski" class="mw-redirect" title="Leon Marchlewski">Leon Marchlewski</a> erst 1893, Rubiadin-<a href="Glucoside" title="Glucoside">Glucosid</a> aus der niederländischen Krappwurzel zu isolieren. Die erste Synthese der Verbindung gelang 1927.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Rubiadin kommt in Pflanzen der Gattung <i><a href="F%C3%A4rberr%C3%B6ten" title="Färberröten">Rubia</a></i> und anderen vor.<sup id="cite_ref-caymanchem.com_4-1" class="reference"><a href="#cite_note-caymanchem.com-4"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Herbert_Baxter,_J.B._Harborne,_Gerald_P._Moss_6-0" class="reference"><a href="#cite_note-Herbert_Baxter,_J.B._Harborne,_Gerald_P._Moss-6"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Es ist eines der Pigmente des <a href="F%C3%A4rberkrapp" title="Färberkrapp">Färberkrapps</a>, in der es als <a href="Glucosid" class="mw-redirect" title="Glucosid">Glucosid</a> vorkommt. Sein Monomethylether wurde aus <i>Morinda longiflora</i> und <i><a href="Morinda_citrifolia" class="mw-redirect" title="Morinda citrifolia">Morinda citrifolia</a></i> isoliert.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Gewinnung_und_Darstellung">Gewinnung und Darstellung</h2></div>
<p>Es wurden mehrere Synthesemethoden für Rubiadin beschrieben. Eine davon ist die Synthese von Rubiadin aus <a href="Phthals%C3%A4ureanhydrid" title="Phthalsäureanhydrid">Phthalsäureanhydrid</a> und <a href="2%2C6-Dihydroxytoluol" class="mw-redirect" title="2,6-Dihydroxytoluol">2,6-Dihydroxytoluol</a> in zwei Reaktionsschritten. Die Ausbeuten beider Reaktionsschritte waren jedoch gering (33 % bzw. 54 %). Darüber hinaus war die Reproduzierbarkeit dieser Methode sehr schlecht. Eine weitere Synthesemethode für Rubiadin erfolgt über 2-Methylpurpurin (1,3,4-Trihydroxy-2-methylanthrachinon). Diese Methode erfordert jedoch fünf Schritte, und die Ausbeute jedes Reaktionsschritts ist gering. Eine weitere beschriebene Synthese von Rubiadinderivaten erfolgt unter Verwendung von <a href="Diels-Alder-Reaktion" title="Diels-Alder-Reaktion">Diels-Alder-Reaktionen</a> mit halogenierten Naphthochinonen und <a href="Diene" title="Diene">Dienen</a>. Daneben kann Rubiadin durch die Kondensation von 3-Brom-2,6-dimethoxytoluol mit einem <a href="Phthalid" title="Phthalid">Phthalid</a> gewonnen werden.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Rubiadin ist ein gelber bis oranger Feststoff,<sup id="cite_ref-Sigma_1-5" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-W._Karrer_2-1" class="reference"><a href="#cite_note-W._Karrer-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> der löslich in organischen <a href="L%C3%B6sungsmittel" title="Lösungsmittel">Lösungsmitteln</a> ist.<sup id="cite_ref-caymanchem.com_4-2" class="reference"><a href="#cite_note-caymanchem.com-4"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>Rubiadin ist Bestandteil von natürlichen Farbstoffen.<sup id="cite_ref-K._Lacasse,_Werner_Baumann_11-0" class="reference"><a href="#cite_note-K._Lacasse,_Werner_Baumann-11"><span class="cite-bracket">[</span>10<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-Sigma-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_1-0">a</a></sup> <sup><a href="#cite_ref-Sigma_1-1">b</a></sup> <sup><a href="#cite_ref-Sigma_1-2">c</a></sup> <sup><a href="#cite_ref-Sigma_1-3">d</a></sup> <sup><a href="#cite_ref-Sigma_1-4">e</a></sup> <sup><a href="#cite_ref-Sigma_1-5">f</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/SUPELCO/74553">Rubiadin, analytical standard</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 21. November 2025 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SUPELCO/74553?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-W._Karrer-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-W._Karrer_2-0">a</a></sup> <sup><a href="#cite_ref-W._Karrer_2-1">b</a></sup></span> <span class="reference-text">W. Karrer: <cite style="font-style:italic">Konstitution und Vorkommen der organischen Pflanzenstoffe (exclusive Alkaloide)</cite>. Springer-Verlag, 2013, ISBN 978-3-0348-5142-8, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>502</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=yQycBgAAQBAJ&pg=PA502#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:Rubiadin&rft.au=W.+Karrer&rft.btitle=Konstitution+und+Vorkommen+der+organischen+Pflanzenstoffe+%28exclusive+Alkaloide%29&rft.date=2013&rft.genre=book&rft.isbn=9783034851428&rft.pages=502&rft.pub=Springer-Verlag" style="display:none"> </span></span>
</li>
<li id="cite_note-caymanchem.com-4"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-caymanchem.com_4-0">a</a></sup> <sup><a href="#cite_ref-caymanchem.com_4-1">b</a></sup> <sup><a href="#cite_ref-caymanchem.com_4-2">c</a></sup></span> <span class="reference-text">Cayman Chemical: <a rel="nofollow" class="external text" href="https://www.caymanchem.com/product/11753/rubiadin">Rubiadin (C.I. 75350, CAS Number: 117-02-2) | Cayman Chemical</a>, abgerufen am 21. November 2025.</span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">Elfed Thomas Jones, Alexander Robertson: <cite style="font-style:italic">CCXXIII.—Syntheses of glucosides. Part V. Two new syntheses of rubiadin and syntheses of 1-O-methylrubiadin and of rubiadin glucoside</cite>. In: <cite style="font-style:italic">Journal of the Chemical Society (Resumed)</cite>. <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>0</span>, 1930, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>1699–1709</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/10.1039/JR9300001699">10.1039/JR9300001699</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Rubiadin&rft.atitle=CCXXIII.%E2%80%94Syntheses+of+glucosides.+Part+V.+Two+new+syntheses+of+rubiadin+and+syntheses+of+1-O-methylrubiadin+and+of+rubiadin+glucoside&rft.au=Elfed+Thomas+Jones%2C+Alexander+Robertson&rft.date=1930&rft.doi=10.1039%2FJR9300001699&rft.genre=journal&rft.issue=0&rft.jtitle=Journal+of+the+Chemical+Society+%28Resumed%29&rft.pages=1699-1709" style="display:none"> </span></span>
</li>
<li id="cite_note-Herbert_Baxter,_J.B._Harborne,_Gerald_P._Moss-6"><span class="mw-cite-backlink"><a href="#cite_ref-Herbert_Baxter,_J.B._Harborne,_Gerald_P._Moss_6-0">↑</a></span> <span class="reference-text">Herbert Baxter, J.B. Harborne, Gerald P. Moss: <cite style="font-style:italic">Phytochemical Dictionary A Handbook of Bioactive Compounds from Plants, Second Edition</cite>. CRC Press, 1998, ISBN 0-203-48375-8, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>557</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=oT9ZDwAAQBAJ&pg=PA557#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:Rubiadin&rft.au=Herbert+Baxter%2C+J.B.+Harborne%2C+Gerald+P.+Moss&rft.btitle=Phytochemical+Dictionary+A+Handbook+of+Bioactive+Compounds+from+Plants%2C+Second+Edition&rft.date=1998&rft.genre=book&rft.isbn=0203483758&rft.pages=557&rft.pub=CRC+Press" style="display:none"> </span></span>
</li>
<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">Rainer W. Bussmann, Lothar Hennig, Athanassios Giannis, Jutta Ortwein, Toni M. Kutchan, Xi Feng: <cite style="font-style:italic">Anthraquinone Content in Noni (Morinda citrifolia L.)</cite>. In: <cite style="font-style:italic">Evidence-Based Complementary and Alternative Medicine</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>2013</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, 2013, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>208378</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/10.1155/2013%2F208378">10.1155/2013/208378</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/24062780?dopt=Abstract">PMID 24062780</a>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Rubiadin&rft.atitle=Anthraquinone+Content+in+Noni+%28Morinda+citrifolia+L.%29&rft.au=Rainer+W.+Bussmann%2C+Lothar+Hennig%2C+Athanassios+Giannis%2C+...&rft.date=2013&rft.doi=10.1155%2F2013%2F208378&rft.genre=journal&rft.issue=1&rft.jtitle=Evidence-Based+Complementary+and+Alternative+Medicine&rft.pages=208378&rft.pmid=24062780&rft.volume=2013" style="display:none"> </span></span>
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<li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">Florence D. Stouder, Roger Adams: <cite style="font-style:italic">Polyhydroxy-methylanthraquinones. ix. Contribution to the Structure of Rubiadin</cite>. In: <cite style="font-style:italic">Journal of the American Chemical Society</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>49</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>8</span>, 1927, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>2043–2045</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/10.1021/ja01407a030">10.1021/ja01407a030</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Rubiadin&rft.atitle=Polyhydroxy-methylanthraquinones.+ix.+Contribution+to+the+Structure+of+Rubiadin&rft.au=Florence+D.+Stouder%2C+Roger+Adams&rft.date=1927&rft.doi=10.1021%2Fja01407a030&rft.genre=journal&rft.issue=8&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.pages=2043-2045&rft.volume=49" style="display:none"> </span></span>
</li>
<li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text">Toshiyuki Takano, Tomomi Kondo, Fumiaki Nakatsubo: <cite style="font-style:italic">Facile synthesis of rubiadin by microwave heating</cite>. In: <cite style="font-style:italic">Journal of Wood Science</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>52</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, 2006, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>90–92</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/10.1007/s10086-005-0727-6">10.1007/s10086-005-0727-6</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Rubiadin&rft.atitle=Facile+synthesis+of+rubiadin+by+microwave+heating&rft.au=Toshiyuki+Takano%2C+Tomomi+Kondo%2C+Fumiaki+Nakatsubo&rft.date=2006&rft.doi=10.1007%2Fs10086-005-0727-6&rft.genre=journal&rft.issue=1&rft.jtitle=Journal+of+Wood+Science&rft.pages=90-92&rft.volume=52" style="display:none"> </span></span>
</li>
<li id="cite_note-10"><span class="mw-cite-backlink"><a href="#cite_ref-10">↑</a></span> <span class="reference-text">Mohd Nasarudin Watroly, Mahendran Sekar, Shivkanya Fuloria, Siew Hua Gan, Srikanth Jeyabalan, Yuan Seng Wu, Vetriselvan Subramaniyan, Kathiresan V. Sathasivam, Subban Ravi, Nur Najihah Izzati Mat Rani, Pei Teng Lum, Jaishree Vaijanathappa, Dhanalekshmi Unnikrishnan Meenakshi, Shankar Mani, Neeraj Kumar Fuloria: <cite style="font-style:italic">Chemistry, Biosynthesis, Physicochemical and Biological Properties of Rubiadin: A Promising Natural Anthraquinone for New Drug Discovery and Development</cite>. In: <cite style="font-style:italic">Drug Design, Development and Therapy</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>15</span>, 2021, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>4527–4549</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/10.2147/DDDT.S338548">10.2147/DDDT.S338548</a></span>.<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:Rubiadin&rft.atitle=Chemistry%2C+Biosynthesis%2C+Physicochemical+and+Biological+Properties+of+Rubiadin%3A+A+Promising+Natural+Anthraquinone+for+New+Drug+Discovery+and+Development&rft.au=Mohd+Nasarudin+Watroly%2C+Mahendran+Sekar%2C+Shivkanya+Fuloria%2C+...&rft.btitle=Drug+Design%2C+Development+and+Therapy&rft.date=2021&rft.doi=10.2147%2FDDDT.S338548&rft.genre=book&rft.pages=4527-4549&rft.volume=15" style="display:none"> </span></span>
</li>
<li id="cite_note-K._Lacasse,_Werner_Baumann-11"><span class="mw-cite-backlink"><a href="#cite_ref-K._Lacasse,_Werner_Baumann_11-0">↑</a></span> <span class="reference-text">K. Lacasse, Werner Baumann: <cite style="font-style:italic">Textile Chemicals Environmental Data and Facts</cite>. Springer Science & Business Media, 2012, ISBN 978-3-642-18898-5, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>940</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=7RH2CAAAQBAJ&pg=PA940#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:Rubiadin&rft.au=K.+Lacasse%2C+Werner+Baumann&rft.btitle=Textile+Chemicals+Environmental+Data+and+Facts&rft.date=2012&rft.genre=book&rft.isbn=9783642188985&rft.pages=940&rft.pub=Springer+Science+%26+Business+Media" style="display:none"> </span></span>
</li>
</ol>
<div class="mw-heading mw-heading2"><h2 id="Externe_Links_zu_erwähnten_Verbindungen"><span id="Externe_Links_zu_erw.C3.A4hnten_Verbindungen"></span>Externe Links zu erwähnten Verbindungen</h2></div>
<ol class="references" data-mw-group="S">
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">Externe Identifikatoren von bzw. Datenbank-Links zu <span style="font-style:italic">Natural Red 8 (unspezifiziert)</span>: <a href="CAS-Nummer" title="CAS-Nummer">CAS-Nr.</a>: <span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=12640-73-2">12640-73-2</a><span class="editoronly" style="display:none;"></span>, <a href="Wikidata" title="Wikidata">Wikidata</a>: <a href="https://www.wikidata.org/wiki/Q136958693" class="extiw external" title="d:Q136958693">Q136958693</a>.<span class="editoronly" style="display:none;"></span></span>
</li>
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