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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Morindin</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 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>Morindin
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>26</sub>H<sub>28</sub>O<sub>14</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>gelbe bis gelborange-farbene, glänzende Kristallnadeln<sup id="cite_ref-:0_1-0" class="reference"><a href="#cite_note-:0-1"><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;">Externe Identifikatoren/Datenbanken
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<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><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">60450-21-7</span><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="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/151621">151621</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.133633.html">133633</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/Q27276109" class="extiw external" title="d:Q27276109">Q27276109</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>564,50 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-:0_1-1" class="reference"><a href="#cite_note-:0-1"><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>245 °C<sup id="cite_ref-:0_1-2" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Teilweise Zersetzung ab 155 °C<sup id="cite_ref-:1_2-0" class="reference"><a href="#cite_note-:1-2"><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;">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_3-0" class="reference"><a href="#cite_note-Sigma-3"><span class="cite-bracket">[</span>3<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></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>
</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="Bei Verschlucken: Bei Unwohlsein Giftinformationszentrum, Arzt oder … anrufen. Mund ausspülen.">301+312+330</span></span></a><sup id="cite_ref-Sigma_3-1" class="reference"><a href="#cite_note-Sigma-3"><span class="cite-bracket">[</span>3<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>Morindin</b> ist ein <a href="Glycoside" title="Glycoside">Glycosid</a> der <a href="Primverose" title="Primverose">β-Primverose</a> mit dem <a href="Aglycon" title="Aglycon">Aglycon</a> <a href="Morindon" title="Morindon">Morindon</a>. Es ist eng verwandt mit der <a href="Ruberythrins%C3%A4ure" title="Ruberythrinsäure">Ruberythrinsäure</a> und zeitweise wurde angenommen, dass beide Verbindungen identisch sind.<sup id="cite_ref-:0_1-3" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_2-1" class="reference"><a href="#cite_note-:1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Morindin kommt in der Wurzelrinde verschiedener <i><a href="Morinda" title="Morinda">Morinda</a></i>-Arten vor, darunter dem <a href="Nonibaum" class="mw-redirect" title="Nonibaum">Nonibaum</a> (<i>Morinda citrifolia</i>), <i>Morinda tinctoria</i>, <i>Morinda lucida</i> und <i>Morinda persicaefolia</i>.<sup id="cite_ref-:0_1-4" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:2_4-0" class="reference"><a href="#cite_note-:2-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Daneben kommt es auch in <i>Neonauclea calcyna</i> vor, ebenfalls aus der Familie der <a href="R%C3%B6tegew%C3%A4chse" title="Rötegewächse">Rötegewächse</a>.<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>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Morindin hat eine auffällige gelbe bis gelb-orangefarbene Färbung.<sup id="cite_ref-:0_1-5" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Es ist ein <a href="Antioxidans" title="Antioxidans">Antioxidationsmittel</a> und möglicherweise ein Inhibitor der <a href="Xanthinoxidase" class="mw-redirect" title="Xanthinoxidase">Xanthin-Oxidase</a>.<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>
</p>
<div class="mw-heading mw-heading2"><h2 id="Reaktionen">Reaktionen</h2></div>
<p>Morindin geht verschiedene Farbreaktionen ein und bildet mehrere <a href="Hydrate" title="Hydrate">Hydrate</a>.<sup id="cite_ref-:1_2-2" class="reference"><a href="#cite_note-:1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Es kann durch <a href="Salzs%C3%A4ure" title="Salzsäure">Salzsäure</a> in <a href="Ethanol" title="Ethanol">Ethanol</a> am Rückfluss hydrolysiert werden, wobei Morindon entsteht.<sup id="cite_ref-:0_1-6" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_2-3" class="reference"><a href="#cite_note-:1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Synthese">Synthese</h2></div>
<p>Ausgehend von Opiansäure und 4-Brom-2-methylphenol kann Morindon synthetisiert werden, das dann zu Morindin glycosyliert werden kann.<sup id="cite_ref-:2_4-1" class="reference"><a href="#cite_note-:2-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>Morindin ist für die Färbewirkung natürlicher Morinda-Extrakte verantwortlich, die traditionell als <a href="Farbstoffe" title="Farbstoffe">Farbstoff</a> für rote, violette oder bräunliche Färbungen verwendet werden, z. B. in <a href="Indien" title="Indien">Indien</a> und <a href="Bangladesch" title="Bangladesch">Bangladesch</a>.<sup id="cite_ref-:0_1-7" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_2-4" class="reference"><a href="#cite_note-:1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<div class="mw-references-wrap"><ol class="references">
<li id="cite_note-:0-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-:0_1-0">a</a></sup> <sup><a href="#cite_ref-:0_1-1">b</a></sup> <sup><a href="#cite_ref-:0_1-2">c</a></sup> <sup><a href="#cite_ref-:0_1-3">d</a></sup> <sup><a href="#cite_ref-:0_1-4">e</a></sup> <sup><a href="#cite_ref-:0_1-5">f</a></sup> <sup><a href="#cite_ref-:0_1-6">g</a></sup> <sup><a href="#cite_ref-:0_1-7">h</a></sup></span> <span class="reference-text"><a href="T._E._Thorpe" class="mw-redirect" title="T. E. Thorpe">T. E. Thorpe</a>, T. H. Greenall: <cite style="font-style:italic">VI.—On morindin and morindon</cite>. In: <cite style="font-style:italic"><a href="J._Chem._Soc.%2C_Trans." class="mw-redirect" title="J. Chem. Soc., Trans.">J. Chem. Soc., Trans.</a></cite> <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>51</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>0</span>, 1887, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>52–58</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/CT8875100052">10.1039/CT8875100052</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:Morindin&rft.atitle=VI.%E2%80%94On+morindin+and+morindon&rft.au=T.+E.+Thorpe%2C+T.+H.+Greenall&rft.date=1887&rft.doi=10.1039%2FCT8875100052&rft.genre=journal&rft.issue=0&rft.jtitle=J.+Chem.+Soc.%2C+Trans.&rft.pages=52-58&rft.volume=51" style="display:none"> </span></span>
</li>
<li id="cite_note-:1-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-:1_2-0">a</a></sup> <sup><a href="#cite_ref-:1_2-1">b</a></sup> <sup><a href="#cite_ref-:1_2-2">c</a></sup> <sup><a href="#cite_ref-:1_2-3">d</a></sup> <sup><a href="#cite_ref-:1_2-4">e</a></sup></span> <span class="reference-text">W. Stein: <cite style="font-style:italic">Ueber Morindin und Morindon; ein Beitrag zur näheren Kenntniss derselben</cite>. In: <cite style="font-style:italic"><a href="Journal_f%C3%BCr_Praktische_Chemie" class="mw-redirect" title="Journal für Praktische Chemie">Journal für Praktische Chemie</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>97</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, 1866, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>234–242</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/10.1002/prac.18660970131">10.1002/prac.18660970131</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:Morindin&rft.atitle=Ueber+Morindin+und+Morindon%3B+ein+Beitrag+zur+n%C3%A4heren+Kenntniss+derselben&rft.au=W.+Stein&rft.date=1866&rft.doi=10.1002%2Fprac.18660970131&rft.genre=journal&rft.issue=1&rft.jtitle=Journal+f%C3%BCr+Praktische+Chemie&rft.pages=234-242&rft.volume=97" style="display:none"> </span></span>
</li>
<li id="cite_note-Sigma-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_3-0">a</a></sup> <sup><a href="#cite_ref-Sigma_3-1">b</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/PHL83245">Morindin</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 12. Juli 2023 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SUPELCO/PHL83245?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span><span style="display:none;">Vorlage:Sigma-Aldrich/Name nicht angegeben</span></span>
</li>
<li id="cite_note-:2-4"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-:2_4-0">a</a></sup> <sup><a href="#cite_ref-:2_4-1">b</a></sup></span> <span class="reference-text">Barbara Vermes, Lorand Farkas, Hildebert Wagner: <cite style="font-style:italic">Synthesis and structure proof of morindone 6-O-primeveroside and 6-O-rutinoside</cite>. In: <cite style="font-style:italic"><a href="Phytochemistry" title="Phytochemistry">Phytochemistry</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>19</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, Januar 1980, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>119–121</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/10.1016/0031-9422%2880%2985026-6">10.1016/0031-9422(80)85026-6</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:Morindin&rft.atitle=Synthesis+and+structure+proof+of+morindone+6-O-primeveroside+and+6-O-rutinoside&rft.au=Barbara+Vermes%2C+Lorand+Farkas%2C+Hildebert+Wagner&rft.date=1980-01&rft.doi=10.1016%2F0031-9422%2880%2985026-6&rft.genre=journal&rft.issue=1&rft.jtitle=Phytochemistry&rft.pages=119-121&rft.volume=19" style="display:none"> </span></span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">Hideki Tosa, Munekazu Iinuma, Fujio Asai et al.: <cite style="font-style:italic">Anthraquinones from Neonauclea calycina and Their Inhibitory Activity against DNA Topoisomerase II.</cite> In: <cite style="font-style:italic"><a href="Biological_and_Pharmaceutical_Bulletin" title="Biological and Pharmaceutical Bulletin">Biological and Pharmaceutical Bulletin</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>21</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>6</span>, 1998, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>641–642</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/10.1248/bpb.21.641">10.1248/bpb.21.641</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:Morindin&rft.atitle=Anthraquinones+from+Neonauclea+calycina+and+Their+Inhibitory+Activity+against+DNA+Topoisomerase+II.&rft.au=Hideki+Tosa%2C+Munekazu+Iinuma%2C+Fujio+Asai+et+al.&rft.date=1998&rft.doi=10.1248%2Fbpb.21.641&rft.genre=journal&rft.issue=6&rft.jtitle=Biological+and+Pharmaceutical+Bulletin&rft.pages=641-642&rft.volume=21" style="display:none"> </span></span>
</li>
<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">Lailatul Fitria, Muhammad Hermawan Widyananda, Sefihara Paramitha Sakti: <cite style="font-style:italic">Analysis of Allopurinol, Cucurbitacin B, Morindine, and Piperine as Xanthine Oxidase Inhibitor by Molecular Docking</cite>. In: <cite style="font-style:italic">JSMARTech</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>1</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, 26. Oktober 2019, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>6–11</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/10.21776/ub.jsmartech.2019.001.01.2">10.21776/ub.jsmartech.2019.001.01.2</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:Morindin&rft.atitle=Analysis+of+Allopurinol%2C+Cucurbitacin+B%2C+Morindine%2C+and+Piperine+as+Xanthine+Oxidase+Inhibitor+by+Molecular+Docking&rft.au=Lailatul+Fitria%2C+Muhammad+Hermawan+Widyananda%2C+Sefihara+Paramitha+Sakti&rft.date=2019-10-26&rft.doi=10.21776%2Fub.jsmartech.2019.001.01.2&rft.genre=journal&rft.issue=1&rft.jtitle=JSMARTech&rft.pages=6-11&rft.volume=1" style="display:none"> </span></span>
</li>
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