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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Cycloartenol</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
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<td>Cycloartenol
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<td>Andere Namen
</td>
<td>
<ul><li>(3<i>S</i>,5<i>R</i>,8<i>S</i>,9<i>S</i>,10<i>R</i>,13<i>R</i>,14<i>S</i>,17<i>R</i>)-17-((<i>R</i>)-1,5-Dimethyl-hex-4-enyl)-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[<i>a</i>]phenanthren-3-ol</li>
<li>9,19-Cyclo-24-lanosten-3<i>β</i>-ol</li></ul>
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<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
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<td>C<sub>30</sub>H<sub>50</sub>O
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<td>Kurzbeschreibung
</td>
<td>
<p>weißer Feststoff<sup id="cite_ref-Sigma_1-0" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
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<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><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=469-38-5">469-38-5</a><span class="editoronly" style="display:none;"></span>
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<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
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<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/92110">92110</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/Q586501" class="extiw external" title="d:Q586501">Q586501</a>
</td></tr></tbody></table>
</td></tr>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
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<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
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<td>426,72 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
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<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
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<td>
<p>fest
</p>
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<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<ul><li>215 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-RömppOnline_2-0" class="reference"><a href="#cite_note-RömppOnline-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li>
<li>99 °C (Hydrat)<sup id="cite_ref-RömppOnline_2-1" class="reference"><a href="#cite_note-RömppOnline-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
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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><sup id="cite_ref-Sigma_1-1" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<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;">
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<td><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table>
<p>
</p>
</td></tr>
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<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><i>keine H-Sätze</i>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i><sup id="cite_ref-Sigma_1-2" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<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>Cycloartenol</b> ist eine organische <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a>, genauer ein tetracyclischer <a href="Triterpen" class="mw-redirect" title="Triterpen">Triterpen</a><a href="Alkohole" title="Alkohole">alkohol</a> mit zusätzlichem <a href="Cyclopropane" title="Cyclopropane">Cyclopropan</a>-Ring.
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Cycloartenol kommt natürlich in vielen Pflanzen vor und wurde zum Beispiel im Milchsaft von <a href="Wolfsmilchgew%C3%A4chse" title="Wolfsmilchgewächse">Wolfsmilchgewächsen</a> (Euphorbiaceae), in der <a href="Kartoffel" title="Kartoffel">Kartoffel</a> (<i>Solanum tuberosum</i>) und der <a href="Gew%C3%B6hnliche_Brechnuss" title="Gewöhnliche Brechnuss">Brechnuss</a> (<i>Strychnos nux vomica</i>) nachgewiesen.<sup id="cite_ref-Lexikon_der_Biochemie_3-0" class="reference"><a href="#cite_note-Lexikon_der_Biochemie-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Es ist, zumindest in Spuren, in allen grünen, <a href="Photosynthese" title="Photosynthese">Photosynthese</a> aktiven Pflanzen vorhanden, da es sich hier um das erste nachweisbare Cyclisierungsprodukt von <a href="2%2C3-Epoxysqualen" class="mw-redirect" title="2,3-Epoxysqualen">2,3-Epoxysqualen</a> im Zuge der pflanzlichen <a href="Biosynthese" title="Biosynthese">Biosynthese</a> von <a href="Sterole" class="mw-redirect" title="Sterole">Sterolen</a> bzw. <a href="Phytosterine" title="Phytosterine">Phytosterinen</a> handelt. Die Biosynthese erfolgt dabei aus <a href="Squalen" title="Squalen">Squalen</a> über 2,3-Epoxysqualen.<sup id="cite_ref-RömppOnline_2-2" class="reference"><a href="#cite_note-RömppOnline-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DOI10.1111/j.1432-1033.1969.tb00512.x_4-0" class="reference"><a href="#cite_note-DOI10.1111/j.1432-1033.1969.tb00512.x-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In Tieren wird die Funktion der Verbindung von <a href="Lanosterin" title="Lanosterin">Lanosterin</a> übernommen.<sup id="cite_ref-Gerhard_Richter_5-0" class="reference"><a href="#cite_note-Gerhard_Richter-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Cycloartenol ist ein weißer Feststoff.<sup id="cite_ref-Sigma_1-3" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<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-Sigma-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_1-0">a</a></sup> <sup><a href="#cite_ref-Sigma_1-1">b</a></sup> <sup><a href="#cite_ref-Sigma_1-2">c</a></sup> <sup><a href="#cite_ref-Sigma_1-3">d</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/08172">Cycloartenol, ≥90% (GC)</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 24. April 2014 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIGMA/08172?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-RömppOnline-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-RömppOnline_2-0">a</a></sup> <sup><a href="#cite_ref-RömppOnline_2-1">b</a></sup> <sup><a href="#cite_ref-RömppOnline_2-2">c</a></sup></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://roempp.thieme.de/lexicon/RD-03-03090"><i>Cycloartenol</i></a>. In: <i><a href="R%C3%B6mpp_Online" class="mw-redirect" title="Römpp Online">Römpp Online</a>.</i> Georg Thieme Verlag, abgerufen am 24. April 2014.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Lexikon_der_Biochemie-3"><span class="mw-cite-backlink"><a href="#cite_ref-Lexikon_der_Biochemie_3-0">↑</a></span> <span class="reference-text">Lexikon der Biochemie: <a rel="nofollow" class="external text" href="https://www.spektrum.de/lexikon/biochemie/cycloartenol/1466">Cycloartenol - Lexikon der Biochemie</a>, abgerufen am 24. April 2014.</span>
</li>
<li id="cite_note-DOI10.1111/j.1432-1033.1969.tb00512.x-4"><span class="mw-cite-backlink"><a href="#cite_ref-DOI10.1111/j.1432-1033.1969.tb00512.x_4-0">↑</a></span> <span class="reference-text">U. Eppenberger, L. Hirth, G. Ourisson: <i>Anerobische Cyclisierung von Squalen-2,3-epoxyd zu Cycloartenol in Gewebekulturen von Nicotiana tabacum L.</i> In: <i>European Journal of Biochemistry.</i> 8, 1969, S. 180–183, <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/10.1111/j.1432-1033.1969.tb00512.x">10.1111/j.1432-1033.1969.tb00512.x</a></span>.</span>
</li>
<li id="cite_note-Gerhard_Richter-5"><span class="mw-cite-backlink"><a href="#cite_ref-Gerhard_Richter_5-0">↑</a></span> <span class="reference-text">Gerhard Richter: <cite style="font-style:italic">Stoffwechselphysiologie der Pflanzen: Physiologie und Biochemie des Primär- und Sekundärstoffwechsels</cite>. Georg Thieme, 1997, ISBN 3-13-152346-8, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>347<span style="display:inline-block;width:.2em"> </span>ff</span>. (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=eaSK7HCBwDkC&pg=PA347#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:Cycloartenol&rft.au=Gerhard+Richter&rft.btitle=Stoffwechselphysiologie+der+Pflanzen%3A+Physiologie+und+Biochemie+des+Prim%C3%A4r-+und+Sekund%C3%A4rstoffwechsels&rft.date=1997&rft.genre=book&rft.isbn=3131523468&rft.pages=347+ff.&rft.pub=Georg+Thieme" style="display:none"> </span></span>
</li>
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