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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Caryophyllene</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 float-right" style="text-align:center; font-size:90%">
<tbody><tr>
<td class="hintergrundfarbe6" colspan="4"><b>Caryophyllene</b>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left">Name
</td>
<td>α-Caryophyllen</td>
<td>β-Caryophyllen</td>
<td>γ-Caryophyllen
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left">Strukturformel
</td>
<td><span typeof="mw:File"></span>
</td>
<td><span typeof="mw:File"></span>
</td>
<td><span typeof="mw:File"></span>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left">Andere Namen
</td>
<td>Humulen</td>
<td>E-BCP<br><small>BETA-CARYOPHYLLENE</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></td>
<td>Isocaryophyllen
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><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=6753-98-6">6753-98-6</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=87-44-5">87-44-5</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=118-65-0">118-65-0</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5281520">5281520</a></td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5281515">5281515</a></td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5281522">5281522</a>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td colspan="3">C<sub>15</sub>H<sub>24</sub>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td colspan="3">204,36 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td colspan="2">flüssig</td>
<td>flüssig bis fest<sup id="cite_ref-goodsg_2-0" class="reference"><a href="#cite_note-goodsg-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left">Kurzbeschreibung
</td>
<td>gelblich-grüne Flüssigkeit<sup id="cite_ref-goodsa_3-0" class="reference"><a href="#cite_note-goodsa-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</td>
<td>Flüssigkeit von nelken-<br>bis terpentinähnlichem Geruch<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>
</td>
<td>schwachgelb,<br>holzartiger Geruch<sup id="cite_ref-goodsg_2-1" class="reference"><a href="#cite_note-goodsg-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>166–168 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-goodsa_3-1" class="reference"><a href="#cite_note-goodsa-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</td>
<td>260–261 °C<sup id="cite_ref-goods_5-0" class="reference"><a href="#cite_note-goods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
</td>
<td>125 °C<sup id="cite_ref-Römpp_6-0" class="reference"><a href="#cite_note-Römpp-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Dichte" title="Dichte">Dichte</a>
</td>
<td>0,90–0,91 g·cm<sup>−3</sup><sup id="cite_ref-goodsa_3-2" class="reference"><a href="#cite_note-goodsa-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</td>
<td>0,89 g·cm<sup>−3</sup><sup id="cite_ref-goods_5-1" class="reference"><a href="#cite_note-goods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-<br>Kennzeichnung</a>
</td>
<td>
<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>Achtung<sup id="cite_ref-Sigma_1_7-0" class="reference"><a href="#cite_note-Sigma_1-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>
</td>
<td>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table><sup id="cite_ref-Sigma_2_8-0" class="reference"><a href="#cite_note-Sigma_2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>
</td>
<td>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table><sup id="cite_ref-leer_9-0" class="reference"><a href="#cite_note-leer-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left" rowspan="3"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>
</td>
<td><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>
<td><span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i>
</td>
<td><span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i>
</td></tr>
<tr>
<td><span title="Untervorlage eingebunden: EUH-Sätze"></span><i>keine EUH-Sätze</i>
</td>
<td><span title="Untervorlage eingebunden: EUH-Sätze"></span><i>keine EUH-Sätze</i>
</td>
<td><span title="Untervorlage eingebunden: EUH-Sätze"></span><i>keine EUH-Sätze</i>
</td></tr>
<tr>
<td><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>
</td>
<td><span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i>
</td>
<td><span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i>
</td></tr>
</tbody></table>
<p><b>Caryophyllene</b> (Betonung auf der vorletzten Silbe: <i>Caryophyll<u>e</u>ne</i>) sind <a href="Terpene#Sesquiterpene" title="Terpene">Sesquiterpene</a>, die in <a href="%C3%84therisches_%C3%96l" class="mw-redirect" title="Ätherisches Öl">ätherischen Ölen</a> enthalten sind. Es existieren α-Caryophyllen (Humulen), β-Caryophyllen (abgekürzt <i>E-BCP</i> für (<i><b>E</b></i>)-<b>B</b>eta<b>C</b>aryo<b>p</b>hyllen) und γ-Caryophyllen.<sup id="cite_ref-Römpp_6-1" class="reference"><a href="#cite_note-Römpp-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Caryophyllene finden sich in zahlreichen Pflanzen, wie <a href="Blauer_Eukalyptus" title="Blauer Eukalyptus">Blauer Eukalyptus</a> (<i>Eucalyptus globulus</i>), <a href="Schwarze_Johannisbeere" title="Schwarze Johannisbeere">Schwarze Johannisbeeren</a> (<i>Ribes nigrum</i>), <a href="Echter_Baldrian" title="Echter Baldrian">Baldrian</a> (<i>Valeriana officinalis</i>), <a href="Majoran" title="Majoran">Majoran</a> (<i>Origanum majorana</i>), <a href="Echter_Salbei" title="Echter Salbei">Salbei</a> (<i>Salvia officinalis</i>), <a href="Eukalypten" title="Eukalypten">Eukalyptus</a> (<i>Eucalyptus citriodora</i>), <a href="Gew%C3%BCrznelkenbaum" title="Gewürznelkenbaum">Gewürznelken</a> (<i>Syzygium aromaticum</i>), <a href="Echter_Thymian" title="Echter Thymian">Thymian</a> (<i>Thymus vulgaris</i>), <a href="Kurkuma" title="Kurkuma">Kurkuma</a> (<i>Curcuma longa</i>), Minzen (<i><a href="Mentha_spicata" class="mw-redirect" title="Mentha spicata">Mentha spicata</a></i>, <i><a href="Mentha_longifolia" class="mw-redirect" title="Mentha longifolia">Mentha longifolia</a></i>), <a href="Pfeffer" title="Pfeffer">Pfeffer</a> (<i>Piper nigrum</i>) und <a href="Basilikum_(Gattung)" title="Basilikum (Gattung)">Basilikum-Arten</a>.<sup id="cite_ref-Dr._Duke_10-0" class="reference"><a href="#cite_note-Dr._Duke-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup>
</p><p>α-Caryophyllen hat eine monocyclische Struktur und kommt in <a href="Ageratum" title="Ageratum">Ageratum</a> (<i>Ageratum conyzoides</i>) und in geringen Mengen in <a href="Perilla" title="Perilla">Perilla</a> (<i>Perilla frutescens</i>), Sangura (<i>Hyptis suaveolens</i>) <a href="Ysop" title="Ysop">Ysop</a> (<i>Hyssopus officinalis</i>) und <a href="Gamander" title="Gamander">Gamander</a> (<i>Teucrium cyprium</i>) vor.<sup id="cite_ref-Dr._Duke_ALPHA_11-0" class="reference"><a href="#cite_note-Dr._Duke_ALPHA-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup>
</p><p>β-Caryophyllen ist bicyclisch gebaut, es findet sich unter anderem in <a href="Behaarter_Zweizahn" title="Behaarter Zweizahn">Behaartem Zweizahn</a> (<i>Bidens pilosa</i>),<sup id="cite_ref-Dr._Duke_BETA_12-0" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Pfeffer (<i>Piper nigrum</i>),<sup id="cite_ref-Dr._Duke_BETA_12-1" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Perilla (<i>Perilla frutescens</i>),<sup id="cite_ref-Dr._Duke_BETA_12-2" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Indischer_Wassernabel" title="Indischer Wassernabel">Indischem Wassernabel</a> (<i>Centella asiatica</i>),<sup id="cite_ref-Dr._Duke_BETA_12-3" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Harfenstr%C3%A4ucher" title="Harfensträucher">Harfensträuchern</a> (<i>Coleus barbatus</i>),<sup id="cite_ref-Dr._Duke_BETA_12-4" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Hanf" title="Hanf">Hanf</a><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup>, <a href="Sternanis" class="mw-redirect" title="Sternanis">Sternanis</a>,<sup id="cite_ref-PhyRes2020-1248_14-0" class="reference"><a href="#cite_note-PhyRes2020-1248-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> <a href="Anis-Duftnessel" title="Anis-Duftnessel">Anis-Duftnessel</a>,<sup id="cite_ref-FFJ-2004-351_15-0" class="reference"><a href="#cite_note-FFJ-2004-351-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> <a href="Rosmarin" title="Rosmarin">Rosmarin</a> (<i>Rosmarinus officinalis</i>),<sup id="cite_ref-Dr._Duke_BETA_12-5" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Lindera_benzoin" title="Lindera benzoin">Gewürzholz</a> (<i>Lindera benzoin</i>),<sup id="cite_ref-Dr._Duke_BETA_12-6" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Arznei-Engelwurz" title="Arznei-Engelwurz">Arznei-Engelwurz</a> (<i>Angelica archangelica</i>),<sup id="cite_ref-Dr._Duke_BETA_12-7" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Ceylon-Zimtbaum" title="Ceylon-Zimtbaum">Zimt</a> (<i>Cinnamomum verum</i>),<sup id="cite_ref-Dr._Duke_BETA_12-8" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Oregano" title="Oregano">Oregano</a> (<i>Origanum vulgare</i>),<sup id="cite_ref-Dr._Duke_BETA_12-9" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Ptychopetalum_olacoides" title="Ptychopetalum olacoides">Potenzbaum</a> (<i>Ptychopetalum olacoides</i>),<sup id="cite_ref-Dr._Duke_BETA_12-10" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Basilikum (<i>Ocimum basilicum</i>),<sup id="cite_ref-Dr._Duke_BETA_12-11" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Gewürznelken (<i>Syzygium aromaticum</i>),<sup id="cite_ref-Dr._Duke_BETA_12-12" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Salbei (<i>Salvia officinalis</i>),<sup id="cite_ref-Dr._Duke_BETA_12-13" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="M%C3%B6nchspfeffer" title="Mönchspfeffer">Mönchspfeffer</a> (<i>Vitex agnus-castus</i>),<sup id="cite_ref-Dr._Duke_BETA_12-14" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Petersilie" title="Petersilie">Petersilie</a> (<i>Petroselinum crispum</i>),<sup id="cite_ref-Dr._Duke_BETA_12-15" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Echter_Koriander" title="Echter Koriander">Koriander</a> (<i>Coriandrum sativum</i>),<sup id="cite_ref-Dr._Duke_BETA_12-16" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Boswellia_sacra" title="Boswellia sacra">Balsambaum</a> (<i>Boswellia sacra</i>),<sup id="cite_ref-Dr._Duke_BETA_12-17" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Echter_Sellerie" title="Echter Sellerie">Sellerie</a> (<i>Apium graveolens</i>),<sup id="cite_ref-Dr._Duke_BETA_12-18" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="Echter_K%C3%BCmmel" title="Echter Kümmel">Kümmel</a> (<i>Carum carvi</i>),<sup id="cite_ref-Dr._Duke_BETA_12-19" class="reference"><a href="#cite_note-Dr._Duke_BETA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> und <a href="Hopfen" title="Hopfen">Hopfen</a>.
</p><p>γ-Caryophyllen wurde in <a href="Arznei-Engelwurz" title="Arznei-Engelwurz">Arznei-Engelwurz</a> (<i>Angelica archangelica</i>) nachgewiesen.<sup id="cite_ref-Dr._Duke_GAMMA_16-0" class="reference"><a href="#cite_note-Dr._Duke_GAMMA-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Wirkung">Wirkung</h2></div>
<p>Sergio Rasmann von der Universität de Neuchâtel entdeckte 2005, dass E-BCP von Maispflanzen abgesondert wird, wenn Fraßfeinde (z. B. <a href="Maiswurzelbohrer" class="mw-redirect" title="Maiswurzelbohrer">Maiswurzelbohrer</a>) deren Wurzeln anfressen. Dies lockt räuberische <a href="Nematoden" class="mw-redirect" title="Nematoden">Nematoden</a> (<i>Heterorhabditis megidis</i>) an, welche die Fraßfeinde befallen.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup>
</p><p>β-Caryophyllen wird an der Luft zu Caryophyllenoxid oxidiert, einem Stoff mit schwacher allergieauslösender Wirkung; nach fünf Wochen ist etwa die Hälfte des Caryophyllens umgewandelt.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Pharmakologie">Pharmakologie</h2></div>
<p>β-Caryophyllen ist ein CB<sub>2</sub>-<a href="Cannabinoid" class="mw-redirect" title="Cannabinoid">Cannabinoid</a> und wirkt entzündungshemmend.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Da dieser Wirkstoff im Gegensatz zu anderen bekannten Substanzen, die auf den gleichen CB<sub>2</sub>-Rezeptor, aber nicht auf den <a href="Cannabinoid-Rezeptor_1" title="Cannabinoid-Rezeptor 1">CB<sub>1</sub>-Rezeptor</a> wirken, keine berauschende Wirkung hat, kommt dieser <a href="Naturstoff" title="Naturstoff">Naturstoff</a> als Ausgangspunkt für die Entwicklung neuer Arzneistoffe infrage.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<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/54743"><i><small>BETA-CARYOPHYLLENE</small></i></a> in der <a href="CosIng-Datenbank" title="CosIng-Datenbank">CosIng-Datenbank</a> der EU-Kommission, abgerufen am 13. November 2021.</span>
</li>
<li id="cite_note-goodsg-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-goodsg_2-0">a</a></sup> <sup><a href="#cite_ref-goodsg_2-1">b</a></sup></span> <span class="reference-text">Datenblatt <a rel="nofollow" class="external text" href="http://www.thegoodscentscompany.com/data/rw1382561.html">isocaryophyllene</a> bei <i>Good Scents Company</i>, abgerufen am 11. Juli 2021.</span>
</li>
<li id="cite_note-goodsa-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-goodsa_3-0">a</a></sup> <sup><a href="#cite_ref-goodsa_3-1">b</a></sup> <sup><a href="#cite_ref-goodsa_3-2">c</a></sup></span> <span class="reference-text">Datenblatt <a rel="nofollow" class="external text" href="http://www.thegoodscentscompany.com/data/rw1027221.html">α-Caryophyllene</a> bei <i>Good Scents Company</i>, abgerufen am 7. Juni 2017.</span>
</li>
<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://roempp.thieme.de/lexicon/RD-03-00612"><i>Caryophyllene</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 25. Dezember 2014.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-goods-5"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-goods_5-0">a</a></sup> <sup><a href="#cite_ref-goods_5-1">b</a></sup></span> <span class="reference-text">Datenblatt <a rel="nofollow" class="external text" href="http://www.thegoodscentscompany.com/data/rw1060851.html">beta-Caryophyllene</a> bei <i>Good Scents Company</i>, abgerufen am 7. Juni 2017.</span>
</li>
<li id="cite_note-Römpp-6"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Römpp_6-0">a</a></sup> <sup><a href="#cite_ref-Römpp_6-1">b</a></sup></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://roempp.thieme.de/lexicon/RD-03-00612"><i>Caryophyllene</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 11. Juli 2021.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Sigma_1-7"><span class="mw-cite-backlink"><a href="#cite_ref-Sigma_1_7-0">↑</a></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/53675">a-Humulene</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 27. April 2011 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/53675?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Sigma_2-8"><span class="mw-cite-backlink"><a href="#cite_ref-Sigma_2_8-0">↑</a></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/22075">(–)-trans-Caryophyllene</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 27. April 2011 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIGMA/22075?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-leer-9"><span class="mw-cite-backlink"><a href="#cite_ref-leer_9-0">↑</a></span> <span class="reference-text">keine Einstufung vorhanden</span>
</li>
<li id="cite_note-Dr._Duke-10"><span class="mw-cite-backlink"><a href="#cite_ref-Dr._Duke_10-0">↑</a></span> <span class="reference-text"><span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://phytochem.nal.usda.gov/phytochem/chemicals/show/51147">CARYOPHYLLENE</a></span> (englisch). In: <i>Dr. Duke's Phytochemical and Ethnobotanical Database</i>, Hrsg. <a href="Landwirtschaftsministerium_der_Vereinigten_Staaten" title="Landwirtschaftsministerium der Vereinigten Staaten">U.S. Department of Agriculture</a>, abgerufen am 11. Juli 2021.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Dr._Duke_ALPHA-11"><span class="mw-cite-backlink"><a href="#cite_ref-Dr._Duke_ALPHA_11-0">↑</a></span> <span class="reference-text"><span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://phytochem.nal.usda.gov/phytochem/chemicals/show/49220">ALPHA-CARYOPHYLLENE</a></span> (englisch). In: <i>Dr. Duke's Phytochemical and Ethnobotanical Database</i>, Hrsg. <a href="Landwirtschaftsministerium_der_Vereinigten_Staaten" title="Landwirtschaftsministerium der Vereinigten Staaten">U.S. Department of Agriculture</a>, abgerufen am 11. Juli 2021.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Dr._Duke_BETA-12"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Dr._Duke_BETA_12-0">a</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-1">b</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-2">c</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-3">d</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-4">e</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-5">f</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-6">g</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-7">h</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-8">i</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-9">j</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-10">k</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-11">l</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-12">m</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-13">n</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-14">o</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-15">p</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-16">q</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-17">r</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-18">s</a></sup> <sup><a href="#cite_ref-Dr._Duke_BETA_12-19">t</a></sup></span> <span class="reference-text"><span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://phytochem.nal.usda.gov/phytochem/chemicals/show/50306">BETA-CARYOPHYLLENE</a></span> (englisch). In: <i>Dr. Duke's Phytochemical and Ethnobotanical Database</i>, Hrsg. <a href="Landwirtschaftsministerium_der_Vereinigten_Staaten" title="Landwirtschaftsministerium der Vereinigten Staaten">U.S. Department of Agriculture</a>, abgerufen am 11. Juli 2021.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-13"><span class="mw-cite-backlink"><a href="#cite_ref-13">↑</a></span> <span class="reference-text">Jürg Gertsch, Marco Leonti, Stefan Raduner, Ildiko Racz, Jian-Zhong Chen: <cite style="font-style:italic">Beta-caryophyllene is a dietary cannabinoid</cite>. In: <cite style="font-style:italic">Proceedings of the National Academy of Sciences</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>105</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>26</span>, Juli 2008, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>9099–9104</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/10.1073/pnas.0803601105">10.1073/pnas.0803601105</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/18574142?dopt=Abstract">PMID 18574142</a>, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2449371/">PMC 2449371</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:Caryophyllene&rft.atitle=Beta-caryophyllene+is+a+dietary+cannabinoid&rft.au=J%C3%BCrg+Gertsch%2C+Marco+Leonti%2C+Stefan+Raduner%2C+...&rft.date=2008-07&rft.doi=10.1073%2Fpnas.0803601105&rft.genre=journal&rft.issue=26&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences&rft.pages=9099-9104&rft.pmc=2449371&rft.pmid=18574142&rft.volume=105" style="display:none"> </span></span>
</li>
<li id="cite_note-PhyRes2020-1248-14"><span class="mw-cite-backlink"><a href="#cite_ref-PhyRes2020-1248_14-0">↑</a></span> <span class="reference-text">Jayanta Kumar Patra, Gitishree Das, Sankhadip Bose, Sabyasachi Banerjee, Chethala N. Vishnuprasad, Maria Pilar Rodriguez‐Torres, Han‐Seung Shin: <cite style="font-style:italic">Star anise (Illicium verum): Chemical compounds, antiviral properties, and clinical relevance</cite>. In: <cite style="font-style:italic">Phytotherapy Research</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>34</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>6</span>, Juni 2020, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>1248–1267</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/ptr.6614">10.1002/ptr.6614</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:Caryophyllene&rft.atitle=Star+anise+%28Illicium+verum%29%3A+Chemical+compounds%2C+antiviral+properties%2C+and+clinical+relevance&rft.au=Jayanta+Kumar+Patra%2C+Gitishree+Das%2C+Sankhadip+Bose%2C+...&rft.date=2020-06&rft.doi=10.1002%2Fptr.6614&rft.genre=journal&rft.issue=6&rft.jtitle=Phytotherapy+Research&rft.pages=1248-1267&rft.volume=34" style="display:none"> </span></span>
</li>
<li id="cite_note-FFJ-2004-351-15"><span class="mw-cite-backlink"><a href="#cite_ref-FFJ-2004-351_15-0">↑</a></span> <span class="reference-text">G. R. Mallavarapu, R. N. Kulkarni, K. Baskaran, S. Ramesh: <cite style="font-style:italic">The essential oil composition of anise hyssop grown in India</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>19</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>4</span>, Juli 2004, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>351–353</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.1316">10.1002/ffj.1316</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:Caryophyllene&rft.atitle=The+essential+oil+composition+of+anise+hyssop+grown+in+India&rft.au=G.+R.+Mallavarapu%2C+R.+N.+Kulkarni%2C+K.+Baskaran%2C+...&rft.date=2004-07&rft.doi=10.1002%2Fffj.1316&rft.genre=journal&rft.issue=4&rft.jtitle=Flavour+and+Fragrance+Journal&rft.pages=351-353&rft.volume=19" style="display:none"> </span></span>
</li>
<li id="cite_note-Dr._Duke_GAMMA-16"><span class="mw-cite-backlink"><a href="#cite_ref-Dr._Duke_GAMMA_16-0">↑</a></span> <span class="reference-text"><span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://phytochem.nal.usda.gov/phytochem/chemicals/show/54487">GAMMA-CARYOPHYLLENE</a></span> (englisch). In: <i>Dr. Duke's Phytochemical and Ethnobotanical Database</i>, Hrsg. <a href="Landwirtschaftsministerium_der_Vereinigten_Staaten" title="Landwirtschaftsministerium der Vereinigten Staaten">U.S. Department of Agriculture</a>, abgerufen am 11. Juli 2021.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-17"><span class="mw-cite-backlink"><a href="#cite_ref-17">↑</a></span> <span class="reference-text">Spektrum der Wissenschaft: <i>Parasitenlockstoff gegen Maisschädlinge</i>. November 2009, S. 20–22.</span>
</li>
<li id="cite_note-18"><span class="mw-cite-backlink"><a href="#cite_ref-18">↑</a></span> <span class="reference-text">M. Skold <i>et al.</i> (2006): <i>The fragrance chemical beta-caryophyllene-air oxidation and skin sensitization.</i> In: <i>Food Chem. Toxicol.</i> Bd. 44, Nr. 4, S. 538–545; <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/16226832?dopt=Abstract">PMID 16226832</a>.</span>
</li>
<li id="cite_note-19"><span class="mw-cite-backlink"><a href="#cite_ref-19">↑</a></span> <span class="reference-text">Gertsch, J. <i>et al.</i> (2008): <i>Beta-caryophyllene is a dietary cannabinoid.</i> In: <i>Proc. Natl. Acad. Sci. U.S.A.</i> 105(26): S. 9099–9104; <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/18574142?dopt=Abstract">PMID 18574142</a>; <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/10.1073/pnas.0803601105">10.1073/pnas.0803601105</a></span>.</span>
</li>
<li id="cite_note-20"><span class="mw-cite-backlink"><a href="#cite_ref-20">↑</a></span> <span class="reference-text"><a href="Die_Welt" title="Die Welt">Die Welt</a>: <a rel="nofollow" class="external text" href="https://www.welt.de/gesundheit/article2136517/Pizza-Gewuerze-wirken-gegen-Entzuendungen.html"><i>Pizza-Gewürze wirken gegen Entzündungen</i></a>, 28. Mai 2021</span>
</li>
</ol>
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Normdaten (Sachbegriff): <a href="Gemeinsame_Normdatei" title="Gemeinsame Normdatei">GND</a>: <span class="-print"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4510516-9">4510516-9</a></span> </div>
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