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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Esculetin</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>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>Esculetin
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>6,7-Dihydroxy-2<i>H</i>-chromen-2-on (<a href="IUPAC-Nomenklatur" class="mw-redirect" title="IUPAC-Nomenklatur">IUPAC</a>)</li>
<li>6,7-Dihydroxycumarin</li>
<li>6,7-Dihydroxy-2-benzopyron</li>
<li>Äsculetin</li>
<li>Aesculetin</li>
<li>Cichorigenin</li>
<li><small>ESCULETIN</small> (<a href="Internationale_Nomenklatur_f%C3%BCr_kosmetische_Inhaltsstoffe" title="Internationale Nomenklatur für kosmetische Inhaltsstoffe">INCI</a>)<sup id="cite_ref-CosIng_1-0" class="reference"><a href="#cite_note-CosIng-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><span class="editoronly" style="display:none;"></span></li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>9</sub>H<sub>6</sub>O<sub>4</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>hellgelber Feststoff<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);">
<tbody><tr>
<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=305-01-1">305-01-1</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">206-161-5
</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/100.005.602">100.005.602</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/5281416">5281416</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.4444764.html">4444764</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/Q3058018" class="extiw external" title="d:Q3058018">Q3058018</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>178,14 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
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>271–273 <a href="Grad_Celsius" title="Grad Celsius">°C</a><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>
<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><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="Verursacht Hautreizungen.">315</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="Verursacht schwere Augenreizung.">319</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 die Atemwege reizen.">335</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="Einatmen von Staub / Rauch / Gas / Nebel / Dampf / Aerosol vermeiden.">261</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 Kontakt mit den Augen: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
(Geänderter Text seit Inkraftreten der „8. Anpassung an den Technischen Fortschritt“ am 1. Februar 2018)">305+351+338</span></span></a><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><a href="Toxizit%C3%A4t" title="Toxizität">Toxikologische Daten</a>
</td>
<td>
<p>1500 mg·kg<sup>−1</sup> (<a href="Letale_Dosis" title="Letale Dosis">LD<sub>50</sub></a>, <a href="M%C3%A4use" title="Mäuse">Maus</a>, <a href="Intraperitoneal" title="Intraperitoneal">i.p.</a>)<sup id="cite_ref-Sigma_2-4" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><span class="editoronly" style="display:none;"></span>
</p>
</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>Esculetin</b> ist ein <a href="Cumarin" title="Cumarin">Cumarin</a>-Derivat. In der Natur kommt es unter anderem in <a href="Eschen_(Pflanzengattung)" title="Eschen (Pflanzengattung)">Eschenrinde</a> (<i>Cortex Fraxini</i>) vor, welche in der <a href="Traditionelle_chinesische_Medizin" title="Traditionelle chinesische Medizin">traditionellen chinesische Medizin</a> eingesetzt wird. Die <a href="Wirkung_(Pharmakologie)" title="Wirkung (Pharmakologie)">pharmakologische Wirkung</a> der Eschenrinde beruht dabei unter anderem auf dem Vorhandensein von Esculetin und seines Glycosid <a href="Aesculin" title="Aesculin">Aesculin</a>.<sup id="cite_ref-:0_3-0" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Wirkung">Wirkung</h2></div>
<p>Esculetin ist ein <a href="Antioxidans" title="Antioxidans">Antioxidans</a> und kann dadurch DNA vor Schädigung durch <a href="Oxidativer_Stress" title="Oxidativer Stress">oxidativen Stress</a> schützen. Diese Wirkung konnte z. B. in Versuchen mit Zellkulturen gezeigt werden. Esculetin war dabei in der Lage <a href="Reaktive_Sauerstoffspezies" title="Reaktive Sauerstoffspezies">reaktive Sauerstoffspezies</a> (ROS), welche durch <a href="UV-Licht" class="mw-redirect" title="UV-Licht">UV-Licht</a> gebildet werden können, abzufangen. Diese Beobachtung legt eine vorbeugende Wirkung von Esculetin gegen <a href="Hautkrebs" title="Hautkrebs">Hautkrebs</a> nahe.<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> Esculetin-haltige Naturheilmittel werden außerdem in der <a href="Volksmedizin" title="Volksmedizin">Volksmedizin</a> gegen Leberschäden eingesetzt. Eine vorbeugende Wirkung von Esculetin gegen Leberschäden durch <a href="Paracetamol" title="Paracetamol">Paracetamol</a> konnte in Experimenten mit Mäusen tatsächlich nachgewiesen werden.<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> Die leberschützende Wirkung beruht vermutlich auf der Reaktion von Esculetin mit den, durch das Leberenzym <a href="Cytochrom_P450" title="Cytochrom P450">Cytochrom P450</a> gebildeten, <a href="Radikale_(Chemie)" class="mw-redirect" title="Radikale (Chemie)">freien Radikalen</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> Weitere mögliche Wirkungen gegen u. a. <a href="Diabetes_mellitus" title="Diabetes mellitus">Diabetes</a>, <a href="Adipositas" title="Adipositas">Adipositas</a> oder <a href="Leuk%C3%A4mie" title="Leukämie">Leukämie</a> konnten in Tier- und Zellkultur-Experimente festgestellt werden.<sup id="cite_ref-:0_3-1" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Synthese">Synthese</h2></div>
<p>Synthetisch kann Esculetin ausgehend von <a href="1%2C4-Benzochinon" title="1,4-Benzochinon"><i>p</i>-Benzochinon</a> hergestellt werden. Dieses wird zunächst in einer 1,4-Addition mit <a href="Essigs%C3%A4ureanhydrid" title="Essigsäureanhydrid">Essigsäureanhydrid</a> zu <a href="Hydroxyhydrochinon" class="mw-redirect" title="Hydroxyhydrochinon">Hydroxyhydrochinontriacetat</a> umgesetzt. Letzteres reagiert mit <a href="%C3%84pfels%C3%A4ure" title="Äpfelsäure">Äpfelsäure</a> zu Esculetin.<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> Beide genannten Teilreaktionen benötigen <a href="Schwefels%C3%A4ure" title="Schwefelsäure">Schwefelsäure</a> als <a href="Katalysator" title="Katalysator">Katalysator</a>.
</p><p>Eine weitere Synthesemöglichkeit besteht in der Umsetzung von Hydroxyhydrochinon mit <a href="Propiols%C3%A4ure" title="Propiolsäure">Propiolsäureethylester</a>. Bei dieser Reaktion fungiert <a href="Zinkchlorid" title="Zinkchlorid">Zinkchlorid</a> als Katalysator.<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>
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-CosIng-1"><span class="mw-cite-backlink"><a href="#cite_ref-CosIng_1-0">↑</a></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://ec.europa.eu/growth/tools-databases/cosing/details/85430"><i><small>ESCULETIN</small></i></a> in der <a href="CosIng-Datenbank" title="CosIng-Datenbank">CosIng-Datenbank</a> der EU-Kommission, abgerufen am 22. Oktober 2021.</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> <sup><a href="#cite_ref-Sigma_2-4">e</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/246573">6,7-Dihydroxycoumarin, 98%</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 20. Januar 2017 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/246573?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-:0-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-:0_3-0">a</a></sup> <sup><a href="#cite_ref-:0_3-1">b</a></sup></span> <span class="reference-text">Mao, G., Zhang, S., Song, H., Ding, S., Zhu, P., Wang, X., Liang, C.: <cite style="font-style:italic">Synthesis, biological activities and therapeutic properties of esculetin and its derivatives</cite>. In: <cite style="font-style:italic">JOCPR</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>7</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>4</span>, 2015, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>122–130</span> (<a rel="nofollow" class="external text" href="http://www.jocpr.com/articles/synthesis-biological-activities-and-therapeutic-properties-of-esculetin-and-its-derivatives.pdf">PDF</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:Esculetin&rft.atitle=Synthesis%2C+biological+activities+and+therapeutic+properties+of+esculetin+and+its+derivatives&rft.au=Mao%2C+G.%2C+Zhang%2C+...&rft.date=2015&rft.genre=journal&rft.issue=4&rft.jtitle=JOCPR&rft.pages=122-130&rft.volume=7" style="display:none"> </span></span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">Kaneko, T., Tahara, S., Takaba, F.: <cite style="font-style:italic">Suppression of Lipid Hydroperoxide-Induced Oxidative Damage to Cellular DNA by Esculetin</cite>. In: <cite style="font-style:italic"><a href="Biological_and_Pharmaceutical_Bulletin" title="Biological and Pharmaceutical Bulletin">Biol Pharm Bull.</a></cite> <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>26</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>6</span>, 2003, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>840–844</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.26.840">10.1248/bpb.26.840</a></span> (<a rel="nofollow" class="external text" href="https://www.jstage.jst.go.jp/article/bpb/26/6/26_6_840/_pdf">PDF</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:Esculetin&rft.atitle=Suppression+of+Lipid+Hydroperoxide-Induced+Oxidative+Damage+to+Cellular+DNA+by+Esculetin&rft.au=Kaneko%2C+T.%2C+Tahara%2C+...&rft.date=2003&rft.doi=10.1248%2Fbpb.26.840&rft.genre=journal&rft.issue=6&rft.jtitle=Biol+Pharm+Bull.&rft.pages=840-844&rft.volume=26" 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">Gilani, A. H., Janbaz, K. H., Shah, B. H.: <cite style="font-style:italic">Esculetin prevents liver damage induced by paracetmaol and CCl<sub>4</sub></cite>. In: <cite style="font-style:italic">Pharmacol Res.</cite> <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>37</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, 1998, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>31–35</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/10.1006/phrs.1997.0262">10.1006/phrs.1997.0262</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:Esculetin&rft.atitle=Esculetin+prevents+liver+damage+induced+by+paracetmaol+and+CCl4&rft.au=Gilani%2C+A.+H.%2C+Janbaz%2C+...&rft.date=1998&rft.doi=10.1006%2Fphrs.1997.0262&rft.genre=journal&rft.issue=1&rft.jtitle=Pharmacol+Res.&rft.pages=31-35&rft.volume=37" 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">Lin, W.-L., Wang, C.-J., Yu-Ying, T., Liu, C.-L., Hwang, J.-M., Tseng, T.-H.: <cite style="font-style:italic">Inhibitory effect of esculetin on oxidative damage inducedby t-butyl hydroperoxide in rat liver</cite>. In: <cite style="font-style:italic"><a href="Arch._Toxicol." class="mw-redirect" title="Arch. Toxicol.">Arch. Toxicol.</a></cite> <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>74</span>, 2000, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>467–472</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/s002040000148">10.1007/s002040000148</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:Esculetin&rft.atitle=Inhibitory+effect+of+esculetin+on+oxidative+damage+inducedby+t-butyl+hydroperoxide+in+rat+liver&rft.au=Lin%2C+W.-L.%2C+Wang%2C+...&rft.btitle=Arch.+Toxicol.&rft.date=2000&rft.doi=10.1007%2Fs002040000148&rft.genre=book&rft.pages=467-472&rft.volume=74" 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">Cao, W. Q.; Xue, J. F.; Shi, C. M.; Ding, C. F.; Zhu, X. G.; Liu, F.; Zhou, X. J.: <cite class="lang" lang="zh" dir="auto" style="font-style:italic">6,7-Dihydroxycoumarine</cite>. In: <cite class="lang" lang="zh" dir="auto" style="font-style:italic">Fine Chem. Intermed.</cite> <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>43</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>3</span>, 2013, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>39–41</span> (chinesisch).<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:Esculetin&rft.atitle=6%2C7-Dihydroxycoumarine&rft.au=Cao%2C+W.+Q.%3B+Xue%2C+J.+F.%3B+Shi%2C+...&rft.date=2013&rft.genre=journal&rft.issue=3&rft.jtitle=Fine+Chem.+Intermed.&rft.pages=39-41&rft.volume=43" style="display:none"> </span></span>
</li>
<li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">Yang, X. J.; Gao, H. H.: <cite class="lang" lang="zh" dir="auto" style="font-style:italic">Study on the synthesis of esculetin under microwave irradiation</cite>. In: <cite class="lang" lang="zh" dir="auto" style="font-style:italic">Appl. Chem. Ind.</cite> <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>40</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>4</span>, 2011, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>627–629</span> (chinesisch, <a rel="nofollow" class="external text" href="http://en.cnki.com.cn/Article_en/CJFDTOTAL-SXHG201104021.htm">englisches Abstract</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:Esculetin&rft.atitle=Study+on+the+synthesis+of+esculetin+under+microwave+irradiation&rft.au=Yang%2C+X.+J.%3B+Gao%2C+H.+H.&rft.date=2011&rft.genre=journal&rft.issue=4&rft.jtitle=Appl.+Chem.+Ind.&rft.pages=627-629&rft.volume=40" style="display:none"> </span></span>
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