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<h1 id="firstHeading" class="firstHeading mw-first-heading"><i>trans</i>-2-Octenal</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><i>trans</i>-2-Octenal
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>(<i>E</i>)-Oct-2-enal</li>
<li>2-(<i>E</i>)-Octenal</li>
<li>2-Octen-1-al</li>
<li><small>TRANS-2-OCTENAL</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>8</sub>H<sub>14</sub>O
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>farblose Flüssigkeit<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=2548-87-0">2548-87-0</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">219-833-8
</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/100.018.031">100.018.031</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/5283324">5283324</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/Q2448755" class="extiw external" title="d:Q2448755">Q2448755</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>126,20 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>flüssig<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="Dichte" title="Dichte">Dichte</a>
</td>
<td>
<p>0,846 g·cm<sup>−3</sup> (25 °C)<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>
</p>
</td></tr>
<tr>
<td><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>
<p>84–86 °C (25 hPa)<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>
</p>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<ul><li>nahezu unlöslich in Wasser<sup id="cite_ref-FiSci_3-0" class="reference"><a href="#cite_note-FiSci-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li>
<li>löslich in <a href="Ethanol" title="Ethanol">Ethanol</a> und Ölen<sup id="cite_ref-FiSci_3-1" class="reference"><a href="#cite_note-FiSci-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<td><a href="Brechungsindex" title="Brechungsindex">Brechungsindex</a>
</td>
<td>
<p>1,45 (20 °C)<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>
</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_2-5" 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_2-6" 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). Brechungsindex: <a href="Natrium-D-Linie" title="Natrium-D-Linie">Na-D-Linie</a>, 20 °C
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b><i>trans</i>-2-Octenal</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Gruppe der <a href="Alkenale" title="Alkenale">Alkenale</a>, also einem <a href="Aldehyd" class="mw-redirect" title="Aldehyd">Aldehyd</a> mit einer zusätzlichen C-C-<a href="Doppelbindung" title="Doppelbindung">Doppelbindung</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p><i>trans</i>-2-Octenal kommt natürlich als wichtiger Aromastoff unter anderem in <a href="Pilze" title="Pilze">Pilzen</a><sup id="cite_ref-Heath_S269_4-0" class="reference"><a href="#cite_note-Heath_S269-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> und Lammfleisch<sup id="cite_ref-Ternes_S468_5-0" class="reference"><a href="#cite_note-Ternes_S468-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>, sowie in verschiedenen Früchten wie Melonen<sup id="cite_ref-FiSci_3-2" class="reference"><a href="#cite_note-FiSci-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> vor.
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p><i>trans</i>-2-Octenal ist eine farblose Flüssigkeit mit grünem zitrusähnlichem Geruch.<sup id="cite_ref-Sigma_2-7" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rowe_6-0" class="reference"><a href="#cite_note-Rowe-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p><i>trans</i>-2-Octenal wird zur Synthese anderer chemischer Verbindungen verwendet.<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>
</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/40527"><i><small>TRANS-2-OCTENAL</small></i></a> in der <a href="CosIng-Datenbank" title="CosIng-Datenbank">CosIng-Datenbank</a> der EU-Kommission, abgerufen am 26. März 2022.</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> <sup><a href="#cite_ref-Sigma_2-5">f</a></sup> <sup><a href="#cite_ref-Sigma_2-6">g</a></sup> <sup><a href="#cite_ref-Sigma_2-7">h</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/W321508">trans-2-Octenal, ≥94%</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 9. Mai 2012 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/W321508?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-FiSci-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-FiSci_3-0">a</a></sup> <sup><a href="#cite_ref-FiSci_3-1">b</a></sup> <sup><a href="#cite_ref-FiSci_3-2">c</a></sup></span> <span class="reference-text"><span class="cite"><a rel="nofollow" class="external text" href="https://www.fishersci.de/shop/products/trans-2-octenal-95-thermo-scientific/11413108"><i>trans-2-Octenal, 95 %, Thermo Scientific Chemicals – Fisher Scientific.</i></a> In: <i>fishersci.de.</i><span class="Abrufdatum"> Abgerufen am 27. September 2024</span>.</span><span style="display: none;" class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rfr_id=info%3Asid%2Fde.wikipedia.org%3ATrans-2-Octenal&rft.title=trans-2-Octenal%2C+95+%25%2C+Thermo+Scientific+Chemicals+%E2%80%93+Fisher+Scientific&rft.description=trans-2-Octenal%2C+95+%25%2C+Thermo+Scientific+Chemicals+%E2%80%93+Fisher+Scientific&rft.identifier="> </span></span>
</li>
<li id="cite_note-Heath_S269-4"><span class="mw-cite-backlink"><a href="#cite_ref-Heath_S269_4-0">↑</a></span> <span class="reference-text">Henry B. Heath: <cite style="font-style:italic">Source Book of Flavors</cite>. Springer, 1981, ISBN 978-0-87055-370-7, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>269</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:Trans-2-Octenal&rft.au=Henry+B.+Heath&rft.btitle=Source+Book+of+Flavors&rft.date=1981&rft.genre=book&rft.isbn=9780870553707&rft.pages=269&rft.pub=Springer" style="display:none"> </span></span>
</li>
<li id="cite_note-Ternes_S468-5"><span class="mw-cite-backlink"><a href="#cite_ref-Ternes_S468_5-0">↑</a></span> <span class="reference-text">Waldemar Ternes: <cite style="font-style:italic">Naturwissenschaftliche Grundlagen der Lebensmittelzubereitung</cite>. Behr’s, 2008, ISBN 978-3-89947-422-0, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>468</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:Trans-2-Octenal&rft.au=Waldemar+Ternes&rft.btitle=Naturwissenschaftliche+Grundlagen+der+Lebensmittelzubereitung&rft.date=2008&rft.genre=book&rft.isbn=9783899474220&rft.pages=468&rft.pub=Behr%E2%80%99s" style="display:none"> </span></span>
</li>
<li id="cite_note-Rowe-6"><span class="mw-cite-backlink"><a href="#cite_ref-Rowe_6-0">↑</a></span> <span class="reference-text">David Rowe: <cite style="font-style:italic">Chemistry and Technology of Flavours and Fragrances</cite>. John Wiley & Sons, 2009, ISBN 978-1-4051-4807-8, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>71</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=HC11GU5KDtgC&pg=PA71#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:Trans-2-Octenal&rft.au=David+Rowe&rft.btitle=Chemistry+and+Technology+of+Flavours+and+Fragrances&rft.date=2009&rft.genre=book&rft.isbn=9781405148078&rft.pages=71&rft.pub=John+Wiley+%26+Sons" 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">Sentaro Okamoto, Kandasamy Subburaj, Fumie Sato: <cite style="font-style:italic">Highly Stereocontrolled Synthesis of Carbacyclin from Acyclic Starting Materials via Ti(II)-Mediated Tandem Cyclization</cite>. In: <cite style="font-style:italic"><a href="Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>122</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>45</span>, 2000, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>11244–11245</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/ja002974x">10.1021/ja002974x</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:Trans-2-Octenal&rft.atitle=Highly+Stereocontrolled+Synthesis+of+Carbacyclin+from+Acyclic+Starting+Materials+via+Ti%28II%29-Mediated+Tandem+Cyclization&rft.au=Sentaro+Okamoto%2C+Kandasamy+Subburaj%2C+Fumie+Sato&rft.date=2000&rft.doi=10.1021%2Fja002974x&rft.genre=journal&rft.issue=45&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.pages=11244-11245&rft.volume=122" style="display:none"> </span></span>
</li>
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