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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Formononetin</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>Formononetin
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>7-Hydroxy-3-(4-methoxyphenyl)-4<i>H</i>-chromen-4-on <small>(<a href="IUPAC-Nomenklatur" class="mw-redirect" title="IUPAC-Nomenklatur">IUPAC</a>)</small></li>
<li>Biochanin B</li>
<li><small>FORMONONETIN</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>
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<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>16</sub>H<sub>12</sub>O<sub>4</sub>
</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=485-72-3">485-72-3</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">207-623-9
</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/100.006.931">100.006.931</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/5280378">5280378</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.4444070.html">4444070</a>
</td></tr>
<tr>
<td><a href="DrugBank" title="DrugBank">DrugBank</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB15335">DB15335</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/Q408859" class="extiw external" title="d:Q408859">Q408859</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>268,26 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>257–261 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-sigma-aldrich_2-0" class="reference"><a href="#cite_note-sigma-aldrich-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
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<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-aldrich_2-1" class="reference"><a href="#cite_note-sigma-aldrich-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-aldrich_2-2" class="reference"><a href="#cite_note-sigma-aldrich-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>Formononetin</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Klasse der <a href="Isoflavone" title="Isoflavone">Isoflavone</a>. Es wird den <a href="Phyto%C3%B6strogene" title="Phytoöstrogene">Phytoöstrogenen</a> zugerechnet, da es sich um eine pflanzliche Verbindung mit <a href="%C3%96strogen" class="mw-redirect" title="Östrogen">östrogenartiger</a> biologischer Aktivität handelt. Die Substanz besitzt keine <a href="Steroide" title="Steroide">steroidale</a> Struktur, ihre Wirkung ist schwach ausgeprägt.
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Formononetin kommt insbesondere in den oberen Pflanzenteilen des <a href="Wiesenklee" title="Wiesenklee">Wiesenklee</a> (Rotklee) vor,<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> ferner auch in bestimmten <a href="H%C3%BClsenfr%C3%BCchtler" title="Hülsenfrüchtler">Hülsenfrüchtler</a>-Arten.
</p>
<p>Es liegt in der Regel <a href="Glycoside" title="Glycoside">glycosidisch</a> gebunden vor; das 7-O-β-D-<a href="Glucopyranose" class="mw-redirect" title="Glucopyranose">Glucopyranosid</a> des Formononetins ist das Ononin.
</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/86785"><i><small>FORMONONETIN</small></i></a> in der <a href="CosIng-Datenbank" title="CosIng-Datenbank">CosIng-Datenbank</a> der EU-Kommission, abgerufen am 1. Oktober 2021.</span>
</li>
<li id="cite_note-sigma-aldrich-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-sigma-aldrich_2-0">a</a></sup> <sup><a href="#cite_ref-sigma-aldrich_2-1">b</a></sup> <sup><a href="#cite_ref-sigma-aldrich_2-2">c</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/SIGMA/47752">Formononetin</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 8. Juni 2011 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIGMA/47752?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">Booth, Nancy L. et al.: <cite style="font-style:italic">Seasonal variation of red clover (Trifolium pratense L., Fabaceae) isoflavones and estrogenic activity</cite>. In: <cite style="font-style:italic">J. Agric. Food Chem.</cite> 54. Jahrgang, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>4</span>, 2006, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>1277–1282</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/jf052927u">10.1021/jf052927u</a></span>, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1903374/">PMC 1903374</a> (freier Volltext).<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:Formononetin&rft.atitle=Seasonal+variation+of+red+clover+%28Trifolium+pratense+L.%2C+Fabaceae%29+isoflavones+and+estrogenic+activity&rft.au=Booth%2C+Nancy+L.+et+al.&rft.date=2006&rft.doi=10.1021%2Fjf052927u&rft.genre=journal&rft.issue=4&rft.jtitle=J.+Agric.+Food+Chem.&rft.pages=1277-1282&rft.pmc=1903374&rft.volume=54.+Jahrgang" style="display:none"> </span></span>
</li>
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