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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Pinocarvon</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>Pinocarvon
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<tr>
<td>Andere Namen
</td>
<td>
<p>6,6-Dimethyl-2-methylenbicyclo[3.1.1]heptan-3-on (<a href="IUPAC-Nomenklatur" class="mw-redirect" title="IUPAC-Nomenklatur">IUPAC</a>)
</p>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>10</sub>H<sub>14</sub>O
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<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);">
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<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=30460-92-5">30460-92-5</a><span class="editoronly" style="display:none;"></span></li>
<li><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">34413-88-2</span><span class="editoronly" style="display:none;"></span> (+)−Form</li>
<li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=19890-00-7">19890-00-7</a><span class="editoronly" style="display:none;"></span> (−)-Form</li></ul>
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<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
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<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a>
</td>
<td colspan="2">250-211-9
</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/100.045.632">100.045.632</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/121719">121719</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.108603.html">108603</a>
</td></tr>
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<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/Q27104017" class="extiw external" title="d:Q27104017">Q27104017</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>150,22 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-Dict_1-0" class="reference"><a href="#cite_note-Dict-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>−1,8 °C (−)-Form<sup id="cite_ref-Dict_1-1" class="reference"><a href="#cite_note-Dict-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>
<ul><li>67–69 °C bei 4 hPa, (−)-Form<sup id="cite_ref-Dict_1-2" class="reference"><a href="#cite_note-Dict-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li>
<li>84–85 °C bei 4 hPa, (+)−Form<sup id="cite_ref-Dict_1-3" class="reference"><a href="#cite_note-Dict-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li></ul>
</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%;">
<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><br><i>keine Einstufung verfügbar</i><sup id="cite_ref-NV_2-0" class="reference"><a href="#cite_note-NV-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>Pinocarvon</b> ist ein <a href="Terpenoide" title="Terpenoide">Terpenoid</a>. Strukturell handelt es sich um ein <a href="Bicyclen" title="Bicyclen">bicyclisches</a> <a href="Ketone" title="Ketone">Keton</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Pinocarvon ist ein wichtiger Bestandteil im <a href="%C3%84therische_%C3%96le" title="Ätherische Öle">ätherischen Öl</a> von <i><a href="Blauer_Eukalyptus" title="Blauer Eukalyptus">Eucalyptus globulus</a></i>.<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> Es kommt außerdem zu einigen Prozent in ätherischen Ölen von anderen <i><a href="Eukalypten" title="Eukalypten">Eucalyptus</a></i>-Arten vor.<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> In mehreren Studien wurde es als Bestandteil von 25 % oder sogar 36 % in <a href="Ysop-%C3%96l" title="Ysop-Öl">Ysop-Öl</a> nachgewiesen.<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><p>Pinocarvon ist außerdem neben <a href="Frontalin" title="Frontalin">Frontalin</a>, <a href="Verbenon" title="Verbenon">Verbenon</a> und <a href="Myrtenol" title="Myrtenol">Myrtenol</a> in <a href="Pheromon" title="Pheromon">Pheromonen</a> des Western Pine Beetle (<i>Dendroctonus brevicomis</i>) enthalten.<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="Eigenschaften_und_Reaktionen">Eigenschaften und Reaktionen</h2></div>
<p>Unter Einfluss von Licht oder Wärme polymerisiert Pinocarvon mittels Reaktion seiner Doppelbindung zu einem Harz. Die Polymerisation kann auch gezielt durchgeführt werden, indem die Verbindung beispielsweise in <a href="Anisol" title="Anisol">Anisol</a> erhitzt wird.<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="Weblinks">Weblinks</h2></div>
<div class="sisterproject" style="margin:0.1em 0 0 0;"><div class="noresize noviewer" style="display:inline-block; line-height:10px; min-width:1.6em; text-align:center;" aria-hidden="true" role="presentation"><span class="mw-default-size" typeof="mw:File"><span title="Commons"></span></span></div><b><span class=""><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Pinocarvones?uselang=de"><span lang="en">Commons</span>: Pinocarvon</a></span></b> – Sammlung von Bildern, Videos und Audiodateien</div>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<div class="mw-references-wrap"><ol class="references">
<li id="cite_note-Dict-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Dict_1-0">a</a></sup> <sup><a href="#cite_ref-Dict_1-1">b</a></sup> <sup><a href="#cite_ref-Dict_1-2">c</a></sup> <sup><a href="#cite_ref-Dict_1-3">d</a></sup></span> <span class="reference-text"><cite style="font-style:italic">Dictionary of Food Compounds with CD-ROM</cite>. CRC Press, ISBN 978-1-4200-6845-0, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>1116</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=eW20PCXIqv8C&pg=PA1116#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:Pinocarvon&rft.btitle=Dictionary+of+Food+Compounds+with+CD-ROM&rft.genre=book&rft.isbn=9781420068450&rft.pages=1116&rft.pub=CRC+Press" style="display:none"> </span></span>
</li>
<li id="cite_note-NV-2"><span class="mw-cite-backlink"><a href="#cite_ref-NV_2-0">↑</a></span> <span class="reference-text">Dieser Stoff wurde in Bezug auf seine Gefährlichkeit entweder noch nicht eingestuft oder eine verlässliche und zitierfähige Quelle hierzu wurde noch nicht gefunden.</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">Wilhelm Treibs, Harry Schmidt: <cite style="font-style:italic">Über das polymere Pinocarvon</cite>. In: <cite style="font-style:italic">Chemische Berichte</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>82</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>3</span>, Mai 1949, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>218–224</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/cber.19490820310">10.1002/cber.19490820310</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:Pinocarvon&rft.atitle=%C3%9Cber+das+polymere+Pinocarvon&rft.au=Wilhelm+Treibs%2C+Harry+Schmidt&rft.date=1949-05&rft.doi=10.1002%2Fcber.19490820310&rft.genre=journal&rft.issue=3&rft.jtitle=Chemische+Berichte&rft.pages=218-224&rft.volume=82" 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">Jorge A. Pino, Rolando Marbot, Rolando Quert, Humberto García: <cite style="font-style:italic">Study of essential oils of Eucalyptus resinifera Smith, E. tereticornis Smith and Corymbia maculata (Hook.) K. D. Hill & L. A. S. Johnson, grown in Cuba</cite>. In: <cite style="font-style:italic">Flavour and Fragrance Journal</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>17</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, Januar 2002, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>1–4</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/ffj.1026">10.1002/ffj.1026</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:Pinocarvon&rft.atitle=Study+of+essential+oils+of+Eucalyptus+resinifera+Smith%2C+E.+tereticornis+Smith+and+Corymbia+maculata+%28Hook.%29+K.+D.+Hill+%26+L.+A.+S.+Johnson%2C+grown+in+Cuba&rft.au=Jorge+A.+Pino%2C+Rolando+Marbot%2C+Rolando+Quert%2C+...&rft.date=2002-01&rft.doi=10.1002%2Fffj.1026&rft.genre=journal&rft.issue=1&rft.jtitle=Flavour+and+Fragrance+Journal&rft.pages=1-4&rft.volume=17" 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">Hakan Özer, Fikrettin Şahin, Hamdullah Kılıç, Medine Güllüce: <cite style="font-style:italic">Essential oil composition of Hyssopus officinalis L. subsp. angustifolius (Bieb.) Arcangeli from Turkey</cite>. In: <cite style="font-style:italic">Flavour and Fragrance Journal</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>20</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, Januar 2005, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>42–44</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/ffj.1421">10.1002/ffj.1421</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:Pinocarvon&rft.atitle=Essential+oil+composition+of+Hyssopus+officinalis+L.+subsp.+angustifolius+%28Bieb.%29+Arcangeli+from+Turkey&rft.au=Hakan+%C3%96zer%2C+Fikrettin+%C5%9Eahin%2C+Hamdullah+K%C4%B1l%C4%B1%C3%A7%2C+...&rft.date=2005-01&rft.doi=10.1002%2Fffj.1421&rft.genre=journal&rft.issue=1&rft.jtitle=Flavour+and+Fragrance+Journal&rft.pages=42-44&rft.volume=20" 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">L.M. Libbey, M.E. Morgan, T.B. Putnam, J.A. Rudinsky: <cite style="font-style:italic">Pheromones released during inter- and intra-sex response of the scolytid beetle Dendroctonus brevicomis</cite>. In: <cite style="font-style:italic">Journal of Insect Physiology</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>20</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>8</span>, August 1974, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>1667–1671</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/10.1016/0022-1910%2874%2990095-X">10.1016/0022-1910(74)90095-X</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:Pinocarvon&rft.atitle=Pheromones+released+during+inter-+and+intra-sex+response+of+the+scolytid+beetle+Dendroctonus+brevicomis&rft.au=L.M.+Libbey%2C+M.E.+Morgan%2C+T.B.+Putnam%2C+...&rft.date=1974-08&rft.doi=10.1016%2F0022-1910%2874%2990095-X&rft.genre=journal&rft.issue=8&rft.jtitle=Journal+of+Insect+Physiology&rft.pages=1667-1671&rft.volume=20" style="display:none"> </span></span>
</li>
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