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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">2-Pinanol</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>
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<tr>
<td colspan="2" style="text-align:center; font-size:80%;">Strukturformel ohne <a href="Stereochemie" title="Stereochemie">Stereochemie</a>
</td></tr>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>2-Pinanol
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>Pinan-2-ol</li>
<li>2,6,6-Trimethylbicyclo[3.1.1]heptan-2-ol</li>
<li><small>PINANAL</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>10</sub>H<sub>18</sub>O
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>farbloser Feststoff<sup id="cite_ref-Ullmann_2-0" class="reference"><a href="#cite_note-Ullmann-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>
<ul><li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=473-54-1">473-54-1</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">35408-04-9</span><span class="editoronly" style="display:none;"></span> [(1<i>R</i>,2<i>R</i>)-Form]</li>
<li><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">35519-42-7</span><span class="editoronly" style="display:none;"></span> [(1<i>R</i>,2<i>S</i>)-Form]</li></ul>
</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">207-466-6
</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/100.006.789">100.006.789</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/10128">10128</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.9723.html">9723</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/Q61472915" class="extiw external" title="d:Q61472915">Q61472915</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>154,28 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>
<ul><li>78–79,2 <a href="Grad_Celsius" title="Grad Celsius">°C</a> (<i>cis</i>-Isomer)<sup id="cite_ref-Ullmann_2-1" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li>
<li>58–59 °C (<i>trans</i>-Isomer)<sup id="cite_ref-Ullmann_2-2" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<td><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>
<ul><li>90–91 °C (<i>cis</i>-Isomer bei 1,5 kPa)<sup id="cite_ref-Ullmann_2-3" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li>
<li>88–89 °C (<i>trans</i>-Isomer bei 0,12 kPa)<sup id="cite_ref-Ullmann_2-4" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
</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><br><i>keine Einstufung verfügbar</i><sup id="cite_ref-NV_3-0" class="reference"><a href="#cite_note-NV-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>2-Pinanol</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Gruppe der <a href="Monoterpene" class="mw-redirect" title="Monoterpene">Monoterpene</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Gewinnung_und_Darstellung">Gewinnung und Darstellung</h2></div>
<p>2-Pinanol kann durch <a href="Hydratisierung" title="Hydratisierung">Hydratisierung</a> (Addition von Wasser) von α-<a href="Pinen" class="mw-redirect" title="Pinen">Pinen</a>, β-Pinen oder einem Isomerengemisch gewonnen werden.<sup id="cite_ref-HSDB_4-0" class="reference"><a href="#cite_note-HSDB-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Sie kann auch durch Oxidation von <a href="Pinan_(chemische_Verbindung)" title="Pinan (chemische Verbindung)">Pinan</a> in Gegenwart von Base, wie <a href="Natriumhydroxid" title="Natriumhydroxid">Natriumhydroxid</a>, und einem Radikalinitiator, wie <a href="Azobisisobutyronitril" class="mw-redirect" title="Azobisisobutyronitril">AIBN</a>, erhalten.<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>
<i>cis</i>-2-Pinanol wird industriell durch die katalytische <a href="Hydrierung" title="Hydrierung">Hydrierung</a> von 2-Pinanhydroperoxid hergestellt. Alternativ kann 2-Pinanhydroperoxid mit <a href="Natriumsulfid" title="Natriumsulfid">Natriumsulfid</a> in wässrigem Natriumhydroxid oder mit <a href="Natriummethoxid" class="mw-redirect" title="Natriummethoxid">Natriummethoxid</a> behandelt werden. <i>cis</i>-2-Pinanol kann auch direkt aus Pinan durch Luftoxidation in Gegenwart von Alkalien, wie beispielsweise Natriumhydroxid, bei 80 bis 100 °C gewonnen werden.<sup id="cite_ref-Ullmann_2-5" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>2-Pinanol ist ein farbloser Feststoff, wobei das <i>cis</i>-Isomer einen dem <a href="Campher" title="Campher">Campher</a> ähnlichen Geruch hat.<sup id="cite_ref-Ullmann_2-6" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<table class="wikitable" style="text-align:center; font-size:90%;">
<tbody><tr>
<td class="hintergrundfarbe6" colspan="3"><b>Stereoisomere von 2-Pinanol</b>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left">Name
</td>
<td><i>cis</i>-2-Pinanol</td>
<td><i>trans</i>-2-Pinanol
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left">Andere Namen
</td>
<td>(1<i>R</i>,2<i>S</i>,5<i>S</i>)-2,6,6-Trimethylbicyclo[3.1.1]heptan-2-ol</td>
<td>(1<i>R</i>,2<i>R</i>,5<i>S</i>)-2,6,6-Trimethylbicyclo[3.1.1]heptan-2-ol
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Strukturformel" title="Strukturformel">Strukturformel</a>
</td>
<td><span typeof="mw:File"></span></td>
<td><span typeof="mw:File"></span>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left" rowspan="2"><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=4948-28-1">4948-28-1</a><span class="editoronly" style="display:none;"></span></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=4948-29-2">4948-29-2</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td colspan="2"><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=473-54-1">473-54-1</a><span class="editoronly" style="display:none;"></span> (unspez.)
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left" rowspan="2"><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6428289">6428289</a></td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/10128">10128</a>
</td></tr>
<tr>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/10128">10128</a> (unspez.)
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left" rowspan="2"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td><a href="https://www.wikidata.org/wiki/Q27254811" class="extiw external" title="d:Q27254811">Q27254811</a></td>
<td><a href="https://www.wikidata.org/wiki/Q98000292" class="extiw external" title="d:Q98000292">Q98000292</a>
</td></tr>
<tr>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q61472915" class="extiw external" title="d:Q61472915">Q61472915</a> (unspez.)
</td></tr>
</tbody></table>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>2-Pinanol wird als <a href="Aromastoff" class="mw-redirect" title="Aromastoff">Aromastoff</a> verwendet.<sup id="cite_ref-HSDB_4-1" class="reference"><a href="#cite_note-HSDB-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Es wird auch als Zwischenprodukt zur Herstellung von Terpenalkoholen,<sup id="cite_ref-Connolly/Hill_6-0" class="reference"><a href="#cite_note-Connolly/Hill-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> wie zum Beispiel <a href="Fenchole" title="Fenchole">α-Fenchol</a><sup id="cite_ref-DOI10.1080/10412905.1996.9700679_7-0" class="reference"><a href="#cite_note-DOI10.1080/10412905.1996.9700679-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> und <a href="Linalool" title="Linalool">Linalool</a><sup id="cite_ref-Eberhard_Breitmaier_8-0" class="reference"><a href="#cite_note-Eberhard_Breitmaier-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DOI10.3390/molecules18078358_9-0" class="reference"><a href="#cite_note-DOI10.3390/molecules18078358-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> verwendet. So liefert die <a href="Pyrolyse" title="Pyrolyse">Pyrolyse</a> von 2-Pinanol bei 500 °C Linalool. (–)-Linalool wird gebildet aus (+)-<i>cis</i>- und (–)-<i>trans</i>-2-Pinanol, und (+)-Linalool aus (–)-<i>cis</i>- und (+)-<i>trans</i>-2-Pinanol.
</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/41018"><i><small>PINANAL</small></i></a> in der <a href="CosIng-Datenbank" title="CosIng-Datenbank">CosIng-Datenbank</a> der EU-Kommission, abgerufen am 14. Oktober 2021.</span>
</li>
<li id="cite_note-Ullmann-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Ullmann_2-0">a</a></sup> <sup><a href="#cite_ref-Ullmann_2-1">b</a></sup> <sup><a href="#cite_ref-Ullmann_2-2">c</a></sup> <sup><a href="#cite_ref-Ullmann_2-3">d</a></sup> <sup><a href="#cite_ref-Ullmann_2-4">e</a></sup> <sup><a href="#cite_ref-Ullmann_2-5">f</a></sup> <sup><a href="#cite_ref-Ullmann_2-6">g</a></sup></span> <span class="reference-text"><cite style="font-style:italic">Ullmann’s Encyclopedia of Industrial Chemistry</cite>. John Wiley & Sons, 2003, ISBN 3-527-30385-5, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>661</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=lYtUAAAAMAAJ&pg=PA661#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:2-Pinanol&rft.btitle=Ullmann%E2%80%99s+Encyclopedia+of+Industrial+Chemistry&rft.date=2003&rft.genre=book&rft.isbn=3527303855&rft.pages=661&rft.pub=John+Wiley+%26amp%3B+Sons" style="display:none"> </span></span>
</li>
<li id="cite_note-NV-3"><span class="mw-cite-backlink"><a href="#cite_ref-NV_3-0">↑</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-HSDB-4"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-HSDB_4-0">a</a></sup> <sup><a href="#cite_ref-HSDB_4-1">b</a></sup></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/source/hsdb/5663"><i>2-Pinanol</i></a> in der <a href="TOXicology_Data_NETwork" title="TOXicology Data NETwork">Hazardous Substances Data Bank</a> (via <a href="PubChem" title="PubChem">PubChem</a>), abgerufen am 4. Februar 2019.<span class="editoronly" 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"><span class="cite">Patent <a rel="nofollow" class="external text" href="https://www.google.com/patents/US3723542A">US3723542A</a>: <i>Process for producing 2-pinanol.</i> Angemeldet am <span style="white-space:nowrap;">23. Januar 1970</span>, veröffentlicht am <span style="white-space:nowrap;">27. Februar 1973</span>, Erfinder: R. Risco, S. Lemberg.</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft_id=US3723542A&rft.applcc=US&rft.title=Process+for+producing+2-pinanol&rft.inventor=R.+Risco%2C+S.+Lemberg&rft.appldate=1970-01-23&rft.pubdate=1973-02-27"></span> abgerufen am 4. Februar 2019.</span>
</li>
<li id="cite_note-Connolly/Hill-6"><span class="mw-cite-backlink"><a href="#cite_ref-Connolly/Hill_6-0">↑</a></span> <span class="reference-text">Connolly/Hill: <cite style="font-style:italic">Dictionary of Terpenoids</cite>. CRC Press, 1991, ISBN 0-412-25770-X, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>140</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=FjnKUcD7-B0C&pg=PA140#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:2-Pinanol&rft.au=Connolly%2FHill&rft.btitle=Dictionary+of+Terpenoids&rft.date=1991&rft.genre=book&rft.isbn=041225770X&rft.pages=140&rft.pub=CRC+Press" style="display:none"> </span></span>
</li>
<li id="cite_note-DOI10.1080/10412905.1996.9700679-7"><span class="mw-cite-backlink"><a href="#cite_ref-DOI10.1080/10412905.1996.9700679_7-0">↑</a></span> <span class="reference-text">Yoshifumi Yuasa, Akira Nagakura, Haruki Tsuruta: <cite style="font-style:italic">A Convenient Synthesis of α-Fenchol from trans-2-Pinanol Using a Solid Acid Catalyst</cite>. In: <cite style="font-style:italic"><a href="Journal_of_Essential_Oil_Research" title="Journal of Essential Oil Research">Journal of Essential Oil Research</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>8</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>5</span>, 1996, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>517–520</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/10.1080/10412905.1996.9700679">10.1080/10412905.1996.9700679</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:2-Pinanol&rft.atitle=A+Convenient+Synthesis+of+%CE%B1-Fenchol+from+trans-2-Pinanol+Using+a+Solid+Acid+Catalyst&rft.au=Yoshifumi+Yuasa%2C+Akira+Nagakura%2C+Haruki+Tsuruta&rft.date=1996&rft.doi=10.1080%2F10412905.1996.9700679&rft.genre=journal&rft.issue=5&rft.jtitle=Journal+of+Essential+Oil+Research&rft.pages=517-520&rft.volume=8" style="display:none"> </span></span>
</li>
<li id="cite_note-Eberhard_Breitmaier-8"><span class="mw-cite-backlink"><a href="#cite_ref-Eberhard_Breitmaier_8-0">↑</a></span> <span class="reference-text"><a href="Eberhard_Breitmaier" title="Eberhard Breitmaier">Eberhard Breitmaier</a>: <cite style="font-style:italic">Terpene Aromen, Düfte, Pharmaka, Pheromone</cite>. John Wiley & Sons, 2012, ISBN 978-3-527-66048-3 (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=9TqDdB8LyNUC">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:2-Pinanol&rft.au=Eberhard+Breitmaier&rft.btitle=Terpene+Aromen%2C+D%C3%BCfte%2C+Pharmaka%2C+Pheromone&rft.date=2012&rft.genre=book&rft.isbn=9783527660483&rft.pub=John+Wiley+%26+Sons" style="display:none"> </span></span>
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<li id="cite_note-DOI10.3390/molecules18078358-9"><span class="mw-cite-backlink"><a href="#cite_ref-DOI10.3390/molecules18078358_9-0">↑</a></span> <span class="reference-text">Janne Leiner <i>et al.</i>: <cite style="font-style:italic">Thermal Behavior of Pinan-2-ol and Linalool</cite>. In: <cite style="font-style:italic"><a href="Molecules" title="Molecules">Molecules</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>18</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>7</span>, Juli 2013, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>8358–8375</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/10.3390/molecules18078358">10.3390/molecules18078358</a></span>, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269951/">PMC 6269951</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:2-Pinanol&rft.atitle=Thermal+Behavior+of+Pinan-2-ol+and+Linalool&rft.au=Janne+Leiner+et+al.&rft.date=2013-07&rft.doi=10.3390%2Fmolecules18078358&rft.genre=journal&rft.issue=7&rft.jtitle=Molecules&rft.pages=8358-8375&rft.pmc=6269951&rft.volume=18" style="display:none"> </span></span>
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