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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Prenole</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"><p><b>Prenole</b> sind <a href="Isoprenoide" title="Isoprenoide">isoprenoide</a> <a href="Alkohole" title="Alkohole">Alkohole</a> mit der allgemeinen Struktur H–[CH<sub>2</sub>–C(CH<sub>3</sub>)=CH–CH<sub>2</sub>]<sub><i>n</i></sub>–OH.<sup id="cite_ref-Gold_Book1_1-0" class="reference"><a href="#cite_note-Gold_Book1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Dabei gibt <i>n</i> die Zahl der <a href="Isopren" title="Isopren">Isopreneinheiten</a> an, die zum Aufbau der Struktur erforderlich sind. Stammverbindung der Prenole ist <a href="Prenol" title="Prenol">Prenol</a> mit <i>n</i> = 1. Liegt <i>n</i> über 4, werden die Verbindungen als <b>Polyprenole</b> bezeichnet.<sup id="cite_ref-Gold_Book2_2-0" class="reference"><a href="#cite_note-Gold_Book2-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Nach der Nomenklatur der <a href="IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> hat ein Prenyl- bzw. ein Polyprenyl-Rest die allgemeine Struktur H–[CH<sub>2</sub>–C(CH<sub>3</sub>)=CH–CH<sub>2</sub>]<sub><i>n</i></sub>–.<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> In der Literatur ist jedoch mit einem Prenyl-Rest oft nur eine Isopreneinheit (3-Methylbut-2-en-1-yl) gemeint.
</p><p><a href="Dolichole" title="Dolichole">Dolichole</a> sind strukturell ähnlich den Polyprenolen, haben jedoch eine gesättigte α-Isopren-Einheit (2,3-Dihydropolyprenole) und bilden eine eigene Stoffgruppe.
</p><p>Beispiele für Prenole sind <a href="Farnesol" title="Farnesol">Farnesol</a> und <a href="Geranylgeraniol" title="Geranylgeraniol">Geranylgeraniol</a>, die in verschiedenen Pflanzen vorkommen. Die Isopreneinheiten haben hier alle <a href="Cis-trans-Isomerie" title="Cis-trans-Isomerie"><i>trans</i>-Stellung</a>. Bei Polyprenolen treten oft <i>trans</i>- und <i>cis</i>-Stellungen innerhalb eines Moleküls auf. Bei den Ficaprenolen, die im <a href="Gummibaum" title="Gummibaum">Gummibaum</a> (<i>Ficus elastica</i>) vorkommen, liegt <i>n</i> bei 10 bis 12, wobei drei in <i>trans</i>- und der Rest in <i>cis</i>-Stellung vorliegt.<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>
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<dl><dd><table class="wikitable" style="text-align:center">
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<td colspan="2">Prenole und Polyprenole (Beispiele)
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<td> <small><a href="Farnesol" title="Farnesol">Farnesol</a></small>
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<td> <small><a href="Geranylgeraniol" title="Geranylgeraniol">Geranylgeraniol</a></small>
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<td colspan="2"><small>Ficaprenol-11</small><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>
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<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
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<li id="cite_note-Gold_Book1-1"><span class="mw-cite-backlink"><a href="#cite_ref-Gold_Book1_1-0">↑</a></span> <span class="reference-text">Eintrag zu <i>prenols.</i> In: <a href="International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a> (Hrsg.): <i><a href="Compendium_of_Chemical_Terminology" title="Compendium of Chemical Terminology">Compendium of Chemical Terminology</a>.</i> The “Gold Book”. <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/10.1351/goldbook.P04816">10.1351/goldbook.P04816</a></span> – Version: 2.3.3.</span>
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<li id="cite_note-Gold_Book2-2"><span class="mw-cite-backlink"><a href="#cite_ref-Gold_Book2_2-0">↑</a></span> <span class="reference-text">Eintrag zu <i>polyprenols.</i> In: <a href="International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a> (Hrsg.): <i><a href="Compendium_of_Chemical_Terminology" title="Compendium of Chemical Terminology">Compendium of Chemical Terminology</a>.</i> The “Gold Book”. <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/10.1351/goldbook.P04750">10.1351/goldbook.P04750</a></span> – Version: 2.3.3.</span>
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<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><a href="IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>-<a href="International_Union_of_Biochemistry" class="mw-redirect" title="International Union of Biochemistry">IUB</a>, Joint Commission on Biochemical Nomenclature, <a rel="nofollow" class="external text" href="https://www.qmul.ac.uk/sbcs/iupac/misc/prenol.html"><i>Prenol nomenclature</i></a>, Recommendations 1986.</span>
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<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://www.spektrum.de/lexikon/biochemie/polyprenole/4958"><i>Polyprenole</i></a>. In: <i>Lexikon der Biochemie</i>, Spektrum Akademischer Verlag, Heidelberg, 1999.</span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">Externe Identifikatoren von bzw. Datenbank-Links zu <span style="font-style:italic">Ficaprenol-11</span>: <a href="CAS-Nummer" title="CAS-Nummer">CAS-Nr.</a>: <span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">26296-50-4</span><span class="editoronly" style="display:none;"></span>, <a href="PubChem" title="PubChem">PubChem</a>: <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/11411688">11411688</a>, <a href="ChemSpider" title="ChemSpider">ChemSpider</a>: <a rel="nofollow" class="external text" href="http://www.chemspider.com/Chemical-Structure.9586576.html">9586576</a>, <a href="Wikidata" title="Wikidata">Wikidata</a>: <a href="https://www.wikidata.org/wiki/Q72478301" class="extiw external" title="d:Q72478301">Q72478301</a>.<span class="editoronly" style="display:none;"></span></span>
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